Indian Patents
Title of Invention

NOVEL QUINOLINE, TETRAHYDROQUINAZOLINE, AND PYRIMIDINE DERIVATIVES AND METHODS OF TREATMENT RELATED TO THE THEREOF
Abstract The present invention relates to novel componends of the Formula (1) which act as MCH receptor antagonists. These compositions are useful in pharmaceutical composition whose use in cludes prophylaxis or treatment of improving memory function sleeping and arousal anxiety depress- sion mood disorders seizure, abesity, diabetes, appetite and eating discorders, cardiovascular disease hypertension, dyslipidemia , myocardial, infarction, binge eating discorders including bulirmia, anorexia, mental discorders including manic depression, schizophrenia, delirium, dementia, stress, cognitive disorders, attention deficit disor- der, substance abuse discorders and dyskinesias including Parkinson’s disease, epilepsy, and addiction.
Full Text

W1461
1096/112
1
DESCRIPTION
NOVEL QUINOLINE, TETRAHYDROQUINAZOLINE, AND PYRIMIDINE
DERIVATIVES AND METHODS OF TREATMENT RELATED
TO THE USE THEREOF
FIELD OF THE INVENTION
The present invention relates to compounds which act as antagonists for MCH receptors and
to the use of these compounds in pharmaceutical compositions.
BACKGROUND OF THE INVENTION
Melanin Concentrating Hormone (MCH), a cyclic peptide, has been identified as the
endogenous ligand of the orphan G-protein coupled receptor SLC-1. See, for example, Shimomura
et al., Biochem. Biophys. Res. Commun. 261, 622-26 (1999). Studies have indicated that MCH acts
as a neurotransmitter/neuromodulator to alter a number of behavioral responses such as feeding habits.
For example, injection of MCH into rats has been reported to increase their consumption of food.
Reports indicate that genetically engineered mice which lack MCH show lower body weight and
increased metabolism. See Saito et al., TEM, vol. 11,299 (2000). As such, the literature suggests that
discovery of MCH antagonists that interact with SCL-1 expressing cells will be useful in developing
obesity treatments. See Shimomura et al., Biochem. Biophys. Res. Commun. 261, 622-26 (1999).
G protein-coupled receptors (GPCRs) share a common structural motif. All these receptors
have seven sequences of between 22 to 24 hydrophobic amino acids that form seven alpha helices,
each of which spans the membrane. The fourth and fifth transmembrane helices are joined on the
extracellular side of the membrane by a strand of amino acids that forms a relatively large loop.
Another larger loop, composed primarily of hydrophilic amino acids, joins transmembrane helices
five and six on the intracellular side of the membrane. The carboxy terminus of the receptor lies
intracellularly, and the amino terminus lies in the extracellular space. It is thought that the loop joining
helices five and six, as well as the carboxy terminus, interact with the G protein. Currently, Gq, Gs,
Gi, and Go are G proteins that have been identified as possible proteins that interact with the receptor.

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Under physiological conditions, GPCRs exist in the cell membrane in equilibrium between
two different states or conformations: an "inactive" state and an "active" state. A receptor in an
inactive state is unable to link to the intracellular transduction pathway to produce a biological
response. Changing the receptor conformation to the active state allows linkage to the transduction
pathway and produces a biological response.
A receptor may be stabilized in an active state by an endogenous ligand or an exogenous
agonist ligand. Recent discoveries, including but not exclusively limited to, modifications to the
amino acid sequence of the receptor, provide alternative mechanisms other than ligands to stabilize the
active state conformation. These approaches effectively stabilize the receptor in an active state by
simulating the effect of a ligand binding to the receptor. Stabilization by such ligand-independent
approaches is termed "constitutive receptor activation." In contrast, antagonists can competitively
bind to the receptor at the same site as agonists, but do not activate the intracellular response initiated
by the active form of the receptor, and therefore inhibit the intracellular responses by agonists.
Certain 2-aminoquinazoline derivatives have been reported to be NPY antagonists which are
said to be effective in the treatment of disorders and diseases associated with the NPY receptor
subtype Y5. See PCT Patent Application 97/20823. Quinazoline derivatives have also been found to
be useful by enhancing antitumor activity. See PCT Patent Application 92/07844. And also the
quinoline derivatives which have an antagonist activity for MCH receptor are known in these patents,
WO03/070244, WO03/105850, WO03/45313, WO03/045920, and WO04/04726.
Recently, our current knowledge of human obesity has advanced dramatically. Previously,
obesity was viewed as an oppugnant behavior of inappropriate eating in the setting of appealing foods.
Studies of animal models of obesity, biochemical alterations in both humans and animals, and the
complex interactions of psychosocial and cultural factors that create receptiveness to human obesity
indicate that this disease in humans is multifaceted and deeply entrenched in biologic systems. Thus,
it is almost certain that obesity has multiple causes and that there are different types of obesity. Not
only does MCHR1 antagonist have potent and durable anti-obesity effects in rodents, it has surprising
antidepressant and anxiolytic properties as well (Borowsky et al., Nature Medicine, 8, 825-830, 2002).
MCHR1 antagonists have been reported to show antidepressant and anxiolytic activities in rodent

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models such as social interaction, forced swimming test and ultrasonic vocalization. These findings
indicate that MCHRI antagonists could be useful for treatment of obesity patients with multiple
causes. Moreover, MCHRI antagonists could be used to treat subjects not only with obesity, but also
those with depression and anxiety. These advantages make it different from NPY receptor antagonists,
with which anxiogenic-like activity can be expected, as NPY itself has anxiolytic-like effect.
Obesity is also regarded as a chronic disease and the possibly of long-term treatment is a
concept that is receiving more attention. In this context, it is noteworthy that the depletion of MCH
leads to hypophagia as well as leanness (Shimada et al., Nature, 396, 670-674, 1998). By contrast,
NPY (Erickson et al., Nature, 381, 415-418, 1996), as well as the Yl (Pedrazzini et al., Nature
Medicine, 4, 722-726, 1998) and Y5 receptors (Marsh et al., Nature Medicine, 4, 718-721, 1998),
disrupted mice maintained a stable body weight or rather became obese. Considering the above
reports, MCHRI antagonists can be more attractive than Yl or Y5 receptor antagonists in terms of
long-term treatment of obese patients.
Obesity, which is the result of an imbalance between caloric intake and energy expenditure, is
highly correlated with insulin resistance and diabetes in experimental animals and human. However, the
molecular mechanisms that are involved in obesity-diabetes syndromes are not clear. During early
development of obesity, increase insulin secretion balances insulin resistance and protects patients from
hyperglycemia (Le Stunff, et al. Diabetes 43, 696-702 (1989)). However, after several decades, (3 cell
function deteriorates and non-insulin-dependent diabetes develops in about 20% of the obese population
(Pederson, P. Diab. Metab. Rev. 5, 505-509 (1989)) and (Brancati, F. L., et al., Arch. Intern. Med. 159,
957-963 (1999)). Given its high prevalence in modem societies, obesity has thus become the leading risk
factor for NIDDM (Hill, J. O., et al., Science 280, 1371-1374 (1998)). However, the factors which
predispose a fraction of patients to alteration of insulin secretion in response to fat accumulation remain
unknown.
Whether someone is classified as overweight or obese is generally determined on the basis of
their body mass index (BMI) which is calculated by dividing body weight (kg) by height squared (m2).
Thus, the units of BMI are kg/nr and it is possible to calculate the BMI range associated with
minimum mortality in each decade of life. Overweight is defined as a BMI in the range 25-30 kg/m2,

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and obesity as a BMI greater than 30 kg/m2 (see TABLE below). There are problems with this
definition in that it does not take into account the proportion of body mass that is muscle in relation to
fat (adipose tissue). To account for this, obesity can also be defined on the basis of body fat content:
greater than 25% and 30% in males and females, respectively.
CLASSIFICATION OF WEIGHT BY
BODY MASS INDEX (BMI)
BMI CLASSIFICATION
18.5-24.9 Normal
25.0-29.9 Overweight
30.0-34.9 Obesity (Class I)
35.0-39.9 Obesity (Class II)
>40 Extreme Obesity (Class III)
As the BMI increases there is an increased risk of death from a variety of causes that is
independent of other risk factors. The most common diseases with obesity are cardiovascular disease
(particularly hypertension), diabetes (obesity aggravates the development of diabetes), gall bladder
disease (particularly cancer) and diseases of reproduction. Research has shown that even a modest
reduction in body weight can correspond to a significant reduction in the risk of developing coronary
heart disease.
Compounds marketed as anti-obesity agents include Orlistat (XENICAL™) and Sibutramine.
Orlistat (a lipase inhibitor) inhibits fat absorption directly and tends to produce a high incidence of
unpleasant (though relatively harmless) side-effects such as diarrhea. Sibutramine (a mixed
5-HT/noradrenaline reuptake inhibitor) can increase blood pressure and heart rate in some patients.
The serotonin releaser/reuptake inhibitors fenfluramine (Pondimin™) and dexfenfluramine
(Redux™) have been reported to decrease food intake and body weight over a prolonged period

5
(greater than 6 months). However, both products were withdrawn after reports of preliminary
evidence of heart valve abnormalities associated with their use. Accordingly, there is a need for the
development of a safer anti-obesity agent.
Obesity considerably increases the risk of developing cardiovascular diseases as well.
Coronary insufficiency, atheromatous disease, and cardiac insufficiency are at the forefront of the
cardiovascular complication induced by obesity. It is estimated that if the entire population had an
ideal weight, the risk of coronary insufficiency would decrease by 25% and the risk of cardiac
insufficiency and of cerebral vascular accidents by 35%. The incidence of coronary diseases is
doubled in subjects less than 50 years of age who are 30% overweight. The diabetes patient faces a
30% reduced Hfespan. After age 45, people with diabetes are about three times more likely than
people without diabetes to have significant heart disease and up to five times more likely to have a
stroke. These findings emphasize the inter-relations between risks factors for NIDDM and coronary
heart disease and the potential value of an integrated approach to the prevention of these conditions
based on the prevention of these conditions based on the prevention of obesity (Perry, I. J., et al., BMJ
310,560-564(1995)).
An increasing number of children and adolescents are overweight. Although not all
overweight children will necessarily become overweight adults, the growing occurrence of obesity in
childhood is likely to be reflected in increasing obesity in adult years. The high prevalence of obesity
in our adult population and the likelihood that the nation of the future will be even more obese
demands a re-examination of the health implications of this disease. See, Health Implications of
Obesity. NIH Consens. Statement Online 1985 Feb 11-13; 5(9):l-7.
"Clinical obesity" is a measurement of the excess body fat relative to lean body mass and is
defined as a body weight more than 20% above the ideal body weight. Recent estimates suggest that
1 in 2 adults in the United States is clinically obese, an increase of more than 25% over the past
decades. Flegal M.D. et al., 22 Int. J. Obes. Relat. Metab. Disor. 39 (1998). Both overweight
conditions and clinical obesity are a major health concerns worldwide, in particular because clinical
obesity is often accompanied by numerous complications, i.e., hypertension and Type II diabetes,
which in turn can cause coronary artery disease, stroke, late-stage complications of diabetes and

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premature death. (See, e.g., Nishina P.M. et al., 43 Metab. 554 (1994)).
Although the etiologic mechanisms underlying obesity require further clarification, the net
effect of such mechanisms leads to an imbalance between energy intake and expenditure. Both genetic
and environmental factors are likely to be involved in the pathogenesis of obesity. These include
excess caloric intake, decreased physical activity, and metabolic and endocrine abnormalities.
Treatment of overweight conditions and clinical obesity via pharmaceutical agents are not
only of importance with respect to the conditions themselves, but also with respect to the possibility
of preventing other diseases that are associated with, e.g., clinical obesity, as well as enhancement of
the positive feeling of "self' that often accompanies those who are overweight or clinically obese and
who encounter a significant reduction in body weight. Given the foregoing discussion, it is apparent
that compounds which help in the treatment of such disorders would be useful and would provide an
advance in both research and clinical medicine. The present invention is directed to these, as well as
other, important ends.
SUMMARY OF THE INVENTION
The present invention is drawn to compounds, which bind to and modulate the activity of a
GPCR referred to herein as MCH, and uses thereof. The term MCH, as used herein, includes the
human sequences found in GeneBank accession number NM_005297, naturally-occurring allelic
variants, mammalian orthologs, biologically active fragments and recombinant mutants thereof.
One aspect of the present invention relates to certain substituted heterocyclic compounds
represented by Formula (I):

wherein Q is:


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R1 is selected from the group consisting of:
(i) C1-16 alkyl, and
C1-16 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••carbocyclic aryl,
••heterocyclyl, and
••heterocyclyl substituted by C1-5 alkyl,
•C1-5 alkylcarbonyloxy,
•carbocyclyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••hydroxy,
••carboxy,
••carbamoyl,
••nitro,
••cyano,

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••amino,
••carbocyclic aryi,
"carbocyclic aryl substituted by C1-5 alkoxy,
"C1-5 alkoxy,
"C1-5 alkoxy substituted by halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
•••halogen,
•••hydroxy,
•••carboxy,
•••oxo,
•"•mono-C1-5 alkylamino,
••*di-C1-5 alkylamino,
•••mono-C1-5 alkylamino substituted by carbocyclic aryl,
•••di-C1-5 alkylamino substituted by carbocyclic aryl,
—mono-C1-5 alkylamino substituted by halogenated
carbocyclic aryl,
•••di-C1-5 alkylamino substituted by halogenated carbocyclic
aryl,
•••carbocyclic arylcarbonylamino, and
•••carbocyclic arylcarbonylamino substituted by halogen,
•heterocyclyloxy,
•heterocyclyloxy substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
"carboxy,

9
—carbamoyl,
••nitro,
••cyano,
••amino,
••carbocyclic aryl,
••carbocyclic aryl substituted by C1-5 alkoxy,
"C1-5 alkoxy,
"C1-5 alkoxy substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
• "hydroxy, and
•••carboxy,
"C1-5 alkyl, and
••C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
•••halogen,
"•hydroxy, and
•••carboxy,
• substituted heterocyc ly 1-ethy 1 iden earn inooxy,
•C1-5 alkoxycarbonyl,
•C1-5 alkoxycarbonyl substituted by carbocyclic aryl,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by substituent(s) independently selected
from the group consisting of:
••cyano,
••carbocyclic aryl, and

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••heterocyclyl,
•di-C1-5 alkylamino,
•di-C1-5 alkylamino substituted by substituent(s) independently selected from
the group consisting of:
••cyano,
••carbocyclic aryl, and
"heterocyclyl,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
••hydroxy,
"carboxy,
••carbamoyl,
••nitro,
"cyano,
—amino,
••carbocyclic aryl,
"•carbocyclic aryl substituted by C1-5 alkoxy,
"C1-5 alkoxy,
••C1-5 alkoxy substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••hydroxy, and
•••carboxy,
"C1-5 alkyl, and
"C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:

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•••halogen,
•••hydroxy, and
•••carboxy,
•di-carbocyclic arylamino,
•di-carbocyclic arylamino substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
••hydroxy,
'•carboxy,
—carbamoyl,
••nitro,
••cyano,
••amino,
••carbocyclic aryl,
••carbocyclic aryl substituted by C1-5 alkoxy,
••C1-5 alkoxy,
•"C1-5 alkoxy substituted by substituent(s) independently selected
from the group consisting of:
—halogen,
•••hydroxy, and
•••carboxy,
•"C1-5 alkyl, and
"•C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
•••halogen,
—hydroxy, and
—carboxy,
•mono-heterocycly lam ino,

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•mono-heterocyclylamino substituted by substituent(s) independently
selected from the group consisting of:
"halogen,
"hydroxy,
••carboxy,
••carbamoyl,
••nitro,
"•cyano,
••amino,
••carbocyclic aryl,
••carbocyclic aryl substituted by C1-5 alkoxy,
"C1-5 alkoxy,
••C1-5 alkoxy substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••hydroxy, and
•••carboxy,
"C1-5 alky], and
••C1-5 alky! substituted by substituent(s) independently selected from
the group consisting of:
•••halogen,
—hydroxy, and
•••carboxy,
•di-heterocyclylamino,
•di-heterocyclylamino substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
"hydroxy,

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••carboxy,
••carbamoyl,
••nitro,
"cyano,
••amino,
"carbocyclic aryl,
••carbocyclic aryl substituted by C1-5 alkoxy,
""C1-5 alkoxy,
••C1-5 alkoxy substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•"hydroxy, and
•••carboxy,
••C1-5 alkyl, and
•*C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
"•halogen,
•••hydroxy, and
•••carboxy,
•C1-5 alkylcarbonylamino,
•C1-5 alkylcarbonylamino substituted by substituent(s) independently
selected from the group consisting of:
"C1-5 alkylcarbonylamino,
••carbocyclic arylcarbonylamino, and
••heterocyclyl,
•C1-5 alkoxycarbonylamino,
•carbocyclic arylcarbonylamino,
•heterocyclyl carbonylamino,

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•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted by substituent(s) independently
selected from the group consisting of:
••nitro,
"C1-5 alkyl,
**mono-C1-5 alkylamino, and
••di-C1-5 alkylamino,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by substituent(s) independently selected from the
group consisting of:
•*mono-carbocyclic arylaminocarbonyl,
••mono-carbocyclic arylaminocarbonyl substituted by halogen,
••di-carbocyclic arylaminocarbonyl,
••di-carbocyclic arylaminocarbonyl substituted by halogen,
"mono-carbocyclic arylamino,
"•mono-carbocyclic arylamino substituted by halogen,
■•di-carbocyclic arylamino,
••di-carbocyclic arylamino substituted by halogen,
••carbocyclic aryl, and
••carbocyclic aryl substituted by substituent(s) independently
selected from the group consisting of:
•••halogen, and
"•C1-5 alkoxy,
•carbocyciic arylthio,
•carbocyclic arylthio substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
"C1-5 alkyl, and

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••C1-5 alkyl substituted by halogen,
•carbocyclic arylsulfmyl,
•carbocyclic arylsulfmyl substituted by substituent(s) independently selected
from the group consisting of:
"halogen,
••C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
"C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
•heterocyclyithio,
•heterocyclylthio substituted by substituent(s) independently selected from
the group consisting of:
"nitro, and
-C ,.s alkyl,
*C3-6 cycloalkyl,
*C3-6 cycloalkyl substituted by d.5 alkyl,
*C3-6 cycloalkyl substituted by carbocyclic aryl,
•C3-6 cycloalkenyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C,_5 alkyl,
••C1-5 alkoxy,

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••C2-5 alkenyl, and
•*C2-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
"•carbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulfinyl,
carbocyclic aryl,
'carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
••hydroxy,
"carboxy,
"carbamoyl,
"cyano,
•■nitro,
••amino,
"C1-5 alkylcarbonylamino,
••C3-6 cycloalkylcarbonylamino,
••d.s alkyl,
"•C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
•••halogen,
""hydroxy,
•"carboxy,
•••carbamoyl,
••"OXO,
•••carbocyclic aryl,
•••heterocyclyl,
"••mono-carbocyciic arylamino,

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•"di-carbocyclic arylamino,
•••mono-carbocyclic arylamino substituted by substituent(s)
independently selected from the group consisting of:
••••halogen,
"••nitro,
••••C|.5 aikyl,
""C1-5 alkoxy, and
••"Ci,5 alkoxy substituted by halogen,
•••di-carbocyclic arylamino substituted by substituent(s)
independently selected from the group consisting of:
••••halogen,
••••nitro,
••••C1-5 aikyl,
••••C1-5 alkoxy, and
••'•C1-5 alkoxy substituted by halogen,
••C2-5 alkenyl,
•*C1-5 alkoxy,
••C1-5 alkoxy substituted by substituent(s) independently selected
from the group consisting of:
—halogen, and
•••carbocyclic aryl,
••carbocyclic aryloxy,
•*C1-5 alkoxycarbonyl,
•*C1-5 alkylcarbonyloxy,
••mono-C1-5 alkylamino,
"di-C1-5 alkylamino,
"mono-carbocyclic arylamino,
••mono-carbocyclic arylamino substituted by halogen,

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••di-carbocyclic arylamino,
••di-carbocyclic arylamino substituted by halogen,
••mono-carbocyclic arylaminocarbonyl,
••mono-carbocyclic arylaminocarbonyl substituted by substituent(s)
selected from the group consisting of:
•"halogen,
"•nitro,
'"C1-5 alkyl,
"••C1-5 alkoxy, and
•••C1-5 alkoxy substituted by halogen,
••di-carbocyclic arylaminocarbonyl,
••di-carbocyclic arylaminocarbonyl substituted by substituent(s)
selected from the group consisting of:
•"halogen,
•••nitro,
—C1-5 alkyl,
•••C1-5 alkoxy, and
*"Cj_5 alkoxy substituted by halogen,
••mercapto,
••C1-5 alkylthio,
•*C1-5 alkylthio substituted by halogen,
"C1-5 alkylsulfonyl,
"C3-6 cycloalkyl,
••carbocyclic aryl, and
••heterocyclyl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:

19
••halogen,
••hydroxy,
■•carboxy,
••carbamoyl,
••cyano,
••nitro,
••amino,
»C,.s alkyl,
"C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
•••halogen,
•••hydroxy,
—carboxy, and
•••carbamoyl,
"C1-5 alkyl substituted by carbocyclic aryl,
"C1-5 alkoxy,
••C1-5 alkoxy substituted by halogen,
"C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryl, and
••carbocyclic aryl substituted by halogen,
(ii) C2.8 alkenyl, and
C2-8 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclic aryl,

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•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
••hydroxy,
••nitro,
-C,_5 alkyl,
"C1-5 alkyl substituted by halogen,
"C1-5 alkoxy, and
"C1-5 alkoxy substituted by halogen,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••hydroxy,
••nitro,
•■C1-5 alkyl, and
••C1-5 alkoxy,
(iii) C2-5 alkynyl, and
C2-5 alkynyl substituted by carbocyclic aryl,
(iv) C3-12 cycloalkyl, and
C3-12 cycloalkyl substituted by substituent(s) independently selected from the
group consisting of:
•C,.s alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••hydroxy,
••0x0, and
••carbocyclic aryl,
•mono-C1-5 alkylamino,

21
•mono-C1-5 alkylamino substituted by carbocyclic aryl,
•di-C1-5 alkylamino,
•di-C]o alkylamino substituted by carbocyclic aryl,
•carbocyclic arylcarbonylamino,
•carbocyclic aryl, and
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
•*C]o alkoxy,
"C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
(v) C3-6 cycloalkenyl, and
C3-6 cycloalkenyl substituted by C1-5 alkyl,
(vi) carbocyclyl, and
carbocyclyl substituted by substitutent(s) independently selected from the
group consisting of:
•hydroxy, and
•nitro,
(vii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•cyano,
-nitro,
•C1-5O alkyl,
•C1-10 alkyl substituted by substituent(s) independently selected from the
group consisting of:

22
••halogen,
"hydroxy,
••carboxy,
••carbamoyl,
"OXO,
"C1-5 alkoxy,
••carbocyclic aryloxy,
••mono-Ci.s alkylamino-N-oxy,
"di-C1-5 alkylamino-N-oxy,
••mono-C1-5 alkylamino,
"di-C1-5 alkylamino,
••mono-C1-5 alkylamino substituted by carbocyclic aryl,
••di-C1-5 alkylamino substituted by carbocyclic aryl,
"mono-carbocyclic arylamino,
"di-carbocyclic arylamino,
••carbocyclylimino,
"carbocyclylimino substituted by carbocyclic aryl,
'•mono-carbocyclic arylamino,
"di-carbocyclic arylamino,
••mono-carbocyclic arylamino substituted by C1-5 alkoxy,
"di-carbocyclic arylamino substituted by C1-5 alkoxy,
••mono-carbocyclic arylaminocarbonyl,
"di-carbocyclic arylaminocarbonyl,
"mono-carbocyclic arylaminocarbonyl substituted by Ct.5 alkoxy,
"di-carbocyclic arylaminocarbonyl substituted by C1-5 alkoxy,
••carbocyclic aryl,
••carbocyclic aryl substituted by substituent(s) independently
selected from the group consisting of:

23
•••halogen,
•••C1-5 alkyl, and
•••C1-5 alkyl substituted by halogen,
••heterocyclyl, and
"heterocyclyl substituted by C1-5 alkyl,
*C2-5 alkenyl,
•C2-5 alkenyl substituted by carbocyclic aryl,
•C1-9 alkoxy,
•C1.9 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••hydroxy,
••halogen,
"carboxy,
"•mono-C1-5 alkylamino,
••di-C1-5 alkylamino,
••carbocyclic aryl,
••halogenated carbocyclic aryl,
••heterocyclyl,
"heterocyclyl substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
—heterocyclyl, and
"•heterocyclyl substituted by substituent(s) independently
selected from the group consisting of:
••••halogen,
••••C1-5 alkyl, and
••••C1-5 alkyl substituted by halogen,
*C2.5 alkenyloxy,

24
•C3-6 cycloalkoxy,
•C1-5 alkylcarbonyloxy,
•carbocyclic aryloxy,
•carbocyclic aryioxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
"hydroxy,
••carboxy,
••carbamoyl,
••cyano,
••nitro,
••ammo,
••Ci-s alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
•••halogen,
•••hydroxy,
•••carboxy, and
•••carbamoyl,
"Ci,5 alkoxy, and
"C1-5 alkoxy substituted by halogen,
• heterocyc ly loxy,
•heterocyclyloxy substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••carboxy,
"carbamoyl,

25
••cyano,
••nitro,
••amino,
••C1-5 alkyl,
"C[.5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
•••halogen,
•••hydroxy,
•"carboxy, and
•••carbamoyl,
"C1-5 alkoxy, and
••C1-5 alkoxy substituted by halogen,
•(carbocyclic aryl)S(O)2O,
•carboxy,
•carbamoyl,
•C1-5 alkoxycarbonyl,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•mono-carbocyclic arylaminocarbonyl,
•di-carbocyclic arylaminocarbonyl,
•mono-carbocyclic arylaminocarbonyl substituted by C\.s alkyl,
•di-carbocyclic arylaminocarbonyl substituted by C\_5 alkyl,
•amino,
*mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,

26
•di-C1-5 alkylamino substituted by cyano,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•C1-5 alkylcarbonylamino,
*C3-6 cycloalkylcarbonylamino,
•C2-5 alkynylcarbonylamino,
•C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,
*C1-5 alkoxycarbonylamino,
•carbocyclic aryl sulfony lam ino,
•carbocyclic arylsulfonylamino substituted by C^ alkyl,
•(carbocyclic aryl)NHC(O)NH,
•(carbocyclic aryI)NHC(O)NH substituted by C1-5 alkoxy,
•(carbocyclic aryl)NHC(O)NH substituted by haloganated C1-5 alkoxy,
•carbocyclic aryl azo,
•carbocyclic aryl azo substituted by mono-C1-5 atkylamino,
•carbocyclic aryl azo substituted by di-C1-5 alkylamino,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by halogen,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by substituent(s) independently selected
from the group consisting of:
—halogen,
••nitre,
••cyano, and
"Cus alkyl,
•aminosulfonyl,
•heterocydylthio,
•C1-5 alkylsulfonyl,

27
•mono-C1-5 alkylaminosulfonyl,
•di-C1-5 alkylaminosulfonyl,
•heterocyclylsulfonyl,
•C3-6 cycloalkyl,
•C3,6 cycloalkyl substituted by C1-5 alkyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••C1.7 alkyl, and
••C].7 alkyl substituted by halogen,
'heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5 alkyl,
"carbocyclic aryl, and
••halogenated carbocyclic aryl,
•C1-5 alkoxycarbonyl substituted by carbocyclic aryl, and
(viii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•carboxy,
•carbamoyl,
•cyano,
•nitro,
•amino,
•C1-5 alkyl,

28
•C1-5 alkyi substituted by substituent(s) independently selected from the
group consisting of:
"halogen,
••hydroxy,
••carboxy,
••carbamoyl,
••oxo,
"C1-5 alkylcarbonyloxy,
"carbocyclic arylcarbonylamino,
••carbocyclic arylcarbonylamino substituted by halogen,
"C1-5 alkoxycarbonyl,
-Cj.5 aikylthio,
"•Cj.5 aikylthio substituted by carbocyclic aryl,
••C1-5 aikylthio substituted by halogenated carbocyclic aryl,
••carbocyclic aryl,
••carbocyclic aryl substituted by substituent(s) independently
selected from the group consisting of:
•••halogen, and
•••nitro,
••heterocyclyl, and
••heterocyclyl substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
—Cj-5 alkyi, and
•••C1-5 alkyi substituted by halogen,
•C)_5 alkoxy,
•C1-5 alkoxy substituted by halogen,
•C1-5 alkoxy substituted by carbocyclic aryl,

29
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
"halogen,
••nitro,
••cyano,
••hydroxy,
••carboxy,
••carbamoyl,
••amino,
»C1-5 alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
"••halogen,
•••hydroxy,
•••carboxy, and
•"•carbamoyl,
••mono-C1-5 alkylamino,
••di-C1-5 alkylammo,
"C1-5 alkylcarbonylamino,
"C3-6 cycloalkycarbonylamino,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by halogen,
"C3-6 cycloalkyl,
"C2-5 alkenyl,
••C2-5alkynyl,
••carboxy,
"•C1-5 alkoxycarbonyl,

30
••mono-C1-5 alkylaminocarbonyl,
••di-C1-5 alkylaminocarbonyl,
'•mono-C3-6 cycloalkylaminocarbonyl,
••di-C3-6cycloalkyIaminocarbonyl,
•'mono-Cj.5 alkylammocarbonylamino,
"di-C1-5 alkylaminocarbonylamino,
•*mono-C3.fi cycloalkylaminocarbonylamino,
"•di-C3-6 cycloalkylaminocarbonylamino,
••C,_5alkylthio,
"C1-5 alkylthio substituted by halogen,
••C1-5 alkylsulfmyl,
••C1-5 alkylsulfmyl substituted by halogen,
"C1-5 alkylsulfonyl, and
"C1-5 alkylsulfonyl substituted by halogen,
•heterocyclyloxy,
•heterocyclyloxy substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,
••hydroxy,
••carboxy,
••carbamoyl,
••cyano,
"■amino,
"C1-5 alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
•••halogen,

31
•••hydroxy,
—carboxy, and
•••carbamoyl,
••C1-5 alkoxy, and
"C1-5 alkoxy substituted by halogen,
•mono-C1-5 alkylamino,
•di-Cj.5 alkylamino,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•Cj-5 alkylcarbonylamino,
•C1-5 alkylthio,
•C2-5 alkenylthio,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by halogen,
•carbocyclic arylthio substituted by Cj.5 alkoxycarbonyl,
•heterocyclylthio,
•heterocyclylthio substituted by C1-5 alkyl,
•C1-5 alkylsulfinyl,
•C1-5 alkylsulfonyl,
•carbocyclic arylsulfinyl,
•carbocyclic arylsulfinyl substituted by halogen,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
••C1-5 alkoxy,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,

32
•C1-5 alkoxycarbonyl,
•C1-5 alkoxycarbonyl substituted by carbocyclic aryl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,
••C1-5 alky!,
••C1-5 alkyl substituted by halogen,
•"C1-5 alkoxy, and
••C1-5 alkoxy substituted by halogen,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
"halogen,
"Ci-s alkyl,
••Cj-5 alkyl substituted by halogen,
"C1-5 alkoxy, and
••C1-5 alkoxycarbonyl;
R2 is selected from the group consisting of:
hydrogen, halogen, hydroxy, carboxy, carbamoyl, amino, C1-5 alkyl, C1-5
alkyl substituted by halogen, C\.$ alkyl substituted by hydroxy, C1-5 alkyl substituted
by carboxy, Ct.5 alkyl substituted by carbamoyl, C1-5 alkoxy, Cj.5 alkoxy substituted
by halogen, -NHNH2, -NHNHBoc, -N(R2a)(R2b), morpholino, 4-acetyl-piperazyl, or
4-phenyI-piperazyI,
wherein R2a is hydrogen or C 1,5 alkyl and R?b is C]-5 alkyl, C3-6 cycloalkyl, or C1-5 alkyl
substituted by substituent(s) independently selected from the group consisting of:

-1 T
•halogen,
•hydroxy,
•carboxy,
•carbamoyl,
•C1-5 alkoxy.,
•amino,
•-NHBoc,
"C3-6 cycloalkyl,
•carbocyclic aryl,
•carbocyciic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
••C1-5 alkyl,
••C1-5 alkoxy, and
-SO2NH2,
•heterocyclyl, and

wherein Boc is carbamic acid tert-buty\ ester and G is C1-5 alkyl or C1-5 alkyl
substituted by substituent(s) independently selected from the group consisting of:
C3 cycloalkyl, carbocyclic aryl, carbocyclic aryl substituted by substituent(s)
independently selected from the group consisting of:
•halogen,
•C1-5 alkyl,
•C].g alkoxy, and
•a group of Formula (V):

34
•carbocyclic ary],
•halogenated carbocyclic aryl, and
•carbocyclic aryl substituted by C1-5 alkoxy;
or R2 is methylamino or dimethylamino when Q is Formula (II) and Y is a single bond
or-CH2-;
Each T is independently selected from the group consisting of halogen, hydroxy,
carboxy, carbamoyl, amino, cyano, nitro, C1-5 alkyl, C1-5 alkyl substituted by halogen,
C1-5 alkyl substituted by hydroxy, C1-5 alkyl substituted by carboxy, C1-5 alkyl
substituted by carbamoyl, C2-5 alkenyl, C2-5 alkynyl, C3-6 cycloalkyl, C1-5 alkoxy, Cj.5
alkoxy substituted by halogen, carbocyclic aryl, heterocyclyl, and -N(R2a)(R2b);
p is 0, 1, 2, 3,4 or 5;
L is selected from the group consisting of Formulae (VI) to (XXI):


35

wherein R3 and R4 are independently hydrogen or C1-5 alkyl; and A and B are
independently a single bond, -CH2-, or -(CH2)2S
and
Y represents:
(i) -C(O)NR5-, -C(S)NR5-, -C(O)O-, -S(O)2-, -C(O)-, -C(S)-, a single bond, or
-CH2- when L is selected from the group consisting of Formulae (VI) to
(XIII); or
(ii) -C(O)NR5-, -C(S)NR5-, -C(O)O- or -OC(O)- when L is selected from the
group consisting of Formulae (XIV) to (XXI);
wherein R5 is hydrogen or C1-5 alkyl, or when Y is -C(O)NR5- then R5 and Ri together
with the nitrogen they are bonded form a heterocyclyl group;
wherein carbocyclic aryl is phenyl, naphthyl, anthranyl, phenanthryl, or
biphenyl;
carbocyclyl is 10,1 l-dihydro-5-oxo-dibenzo[a,d]cycloheptyl, 1-oxo-indanyl,
7,7-dimethyl-2-oxo-bicyclo[2.2.1 ]heptyl, 9#-fluorenyl, 9-oxo-fluoreny 1,
acenaphthyl, anthraquinonyl, C-fluoren-9-yIidene, indanyl, indenyl,
1,2,3,4-tetrahydro-naphthyt, or bicyclo[2.2.1]heptenyl;
heterocyclyl is 1,2,3,4-tetrahydro-isoquinolyl, 1,2,3-thiadiazolyl,
1,2,3-triazolyl, l,2-dihydro-3-oxo-pyrazolyl, 1,3,4-thiadiazolyI, 1,3-dioxo-isoindolyI,

36
1,3-dioxoIanyl, l//-indolyl, l#-pyrrolo[2,3-c]pyridyl, l#-pyrrolyl,
l-oxo-3#-isobenzofiiranyl, 2)2',5')2"-terthiophenyl, 2,2'-bithiophenyl,
2,3-dihydro-l-oxo-isoindoly], 2,3-dihydro-benzo[l,4]dioxinyl,
2,3-dlhydro-benzofuryl, 2,4-dihydro-3-oxo-pyrazolyl, 2/f-benzopyranyl,
2-oxo-benzopyranyl, 2-oxo-pyrrolidinyl, 3,4-dihydro-2//-benzo[l,4]oxazinyl,
3,4-dmydro-2#-benzo[b][l,4]dioxepinyl, 4#-benzo[l,3]dioxinyl, 4#-benzopyranyl,
4-oxo-l,5,6,7-tetrahydro-indoIyl, 4-oxo-3,4-dihydro-phthalazinyI,
4-oxo-benzopyranyl, 9,10,10-trioxo-thioxanthenyl, 9f/-carbazolyl, 9/f-xanthenyl,
azetidinyl, benzimidazolyl, benzo[l,3]dioxolyl, benzo[2,l,3]oxadiazolyl,
benzo[l,2,5]oxadiazolyl, benzo[b]thienyl, benzofuryl, benzothiazolyl, cinnolyl, furyl,
imidazo[2,l-b]thiazolyl, imidazolyl, isoxazolyl, morpholino, morpholinyl, oxazolyl,
oxolanyl, piperazyl, piperidyl, piridyl, pyrazolo[5,l-b]thiazolyl, pyrazolyl, pyrazinyl,
pyridyl, pyrimidyl, pyrrolidyl, quinolyl, quinoxalyl, thiazolidyl, thiazolyl, thienyl,
thiolanyl, 2,3-dihydro-benzofuryl, tetrahydro-thienyl, or benzofuranyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
One aspect of the present invention pertains to pharmaceutical compositions comprising at
least one compound, as described herein, in combination with a pharmaceutically acceptable carrier.
One aspect of the present invention pertains to methods for the prophylaxis or treatment of
improving memory function, sleeping and arousal, anxiety, depression, mood disorders, seizure,
obesity, diabetes, appetite and eating disorders, cardiovascular disease, hypertension, dyslipidemia,
myocardial infarction, binge eating disorders including bulimia, anorexia, mental disorders including
manic depression, schizophrenia, delirium, dementia, stress, cognitive disorders, attention deficit
disorder, substance abuse disorders and dyskinesias including Parkinson's disease, epilepsy, and
addiction comprising administering to an individual suffering from said condition a therapeutically
effective amount of a compound, as described herein, or a pharmaceutical composition thereof.
One aspect of the present invention pertains to methods for the prophylaxis or treatment of an
eating disorder, obesity or an obesity related disorder comprising administering to an individual

37
suffering from the condition a therapeutically effective amount of a compound, as described herein,
or a pharmaceutical composition thereof.
One aspect of the present invention pertains to methods for the prophylaxis or treatment of
anxiety, depression, schizophrenia, addiction, or epilepsy comprising administering to an individual
suffering from the condition a therapeutical ly effective amount of a compound, as described herein,
or a pharmaceutical composition.
One aspect of the present invention pertains to compounds of the present invention, as
described herein, or a pharmaceutical composition thereof, for use in a method of treatment of the
human or animal body by therapy.
One aspect of the present invention pertains to compounds of the present invention, as
described herein, or a pharmaceutical composition thereof, for use in a method of prophylaxis or
treatment of an eating disorder, obesity or an obesity related disorder of the human or animal body by
therapy.
One aspect of the present invention pertains to compounds of the present invention, as
described herein, or a pharmaceutical composition thereof, for use in a method of prophylaxis or
treatment of anxiety, depression, schizophrenia, addiction, or epilepsy of the human or animal body
by therapy.
One aspect of the present invention pertains to compounds of the present invention, as
described herein, for the manufacture of a medicament for use in the prophylaxis or treatment of an
eating disorder, obesity or obesity related disorders.
One aspect of the present invention pertains to compounds of the present invention, as
described herein, for the manufacture of a medicament for use in the prophylaxis or treatment of
anxiety, depression, schizophrenia, addiction, or epilepsy.
One aspect of the present invention pertains to methods of decreasing food intake of an
individual comprising administering to the individual a therapeutically effective amount of a
compound, as described herein, or a pharmaceutical composition thereof.
One aspect of the present invention pertains to methods of inducing satiety in an individual
comprising administering to said individual a therapeutically effective amount of a compound, as

38
described herein, or a pharmaceutical composition thereof.
One aspect of the present invention pertains to methods of controlling or reducing weight gain
in an individual comprising administering to said individual a therapeutically effective amount of a
compound, as described herein, or a pharmaceutical composition thereof.
One aspect of the present invention pertains to methods of modulating a MCH receptor in an
individual comprising contacting the receptor with a compound, as described herein. In some
embodiments, the compound is an antagonist. In some embodiments, the modulation of the MCH
receptor is for the prophylaxis or treatment of an eating disorder, obesity or obesity related disorder.
In some embodiments, the modulation of the MCH receptor reduces food intake of the individual. In
some embodiments, the modulation of the MCH receptor induces satiety in the individual. In some
embodiments, the modulation of the MCH receptor controls or reduces weight gain of the individual.
In some embodiments, the modulation of the MCH receptor is for prophylaxis or treatment of anxiety,
depression, schizophrenia, addiction, or epilepsy.
In some embodiments, the individual is a mammal.
In some embodiments, the mammal is a human.
In some embodiments, the human has a body mass index of about 18.5 to about 45. In some
embodiments, the human has a body mass index of about 25 to about 45. In some embodiments, the
human has a body mass index of about 30 to about 45. In some embodiments, the human has a body
mass index of about 35 to about 45.
One aspect of the present invention pertains to methods of producing a pharmaceutical
composition comprising admixing a compound, as described herein, and a pharmaceutically
acceptable carrier.
This application claims priority to US Provisional Patent Applications, Serial No. 60/458,530,
filed March 31, 2003; Serial No. 60/495,911, filed August 19, 2003; Serial 60/510,186, filed October
9, 2003; and Serial No. 60/530,360, filed December 16, 2003; all of which are incorporated herein by
reference in their entirety.
DETAILED DESCRIPTION OF THE INVENTION

39
One aspect of the present invention relates to certain substituted heterocyclic compounds
represented by Formula (I):

or a pharmaceutically acceptable salt, hydrate or solvate thereof, wherein Q, L, Y, and Ri are as
described herein, supra and infra.
It is appreciated that certain features of the invention, which are, for clarity, described in the
context of separate embodiments, may also be provided in combination in a single embodiment.
Conversely, various features of the invention which are, for brevity, described in the context of a
single embodiment, may also be provided separately or in any suitable subcombination.
In some embodiments of the present invention, R2 is selected from the group consisting of:
hydrogen, halogen, hydroxy., carboxy, carbamoyl, amino, C1-5 alkyl substituted by hydroxy,
C1-5 alkyl substituted by carboxy, C1-5 a'kyl substituted by carbamoyl, C1-5 alkoxy, C1-5 alkoxy
substituted by halogen, -NHNH2, -NHNHBoc, -N(R2a)(R2b), morpholino, 4-acetyl-piperazyl, or
4-phenyl-piperazyI,
wherein R2a is hydrogen or C1-5 alkyl and R2b is C1-5 alkyl, C3-6 cycloalkyl, or C1-5 alkyt
substituted by substituent(s) independently selected from the group consisting of:
•halogen,
•hydroxy,
•carboxy,
•carbamoyl,
•C1-5 alkoxy,
•amino,
•-NHBoc,
•C3-6 cycloalkyl,
•carbocyclic aryl,

40
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
"C1-5 alkyl,
••C1-5 alkoxy, and
-SO2NH2,
•heterocyclyl, and
C3-6 cycloalkyl, carbocyclic aryl, carbocyclic aryl substituted by substituent(s) independently
selected from the group consisting of:
•halogen,
•C1-5 alkyl,
•C1-5 alkoxy, and
•a group of Formula (V):

wherein Boc is carbamic acid ferr-butyl ester and G is C,_5 alkyl or C1-5 alkyl substituted by
substituent(s) independently selected from the group consisting of:
•carbocyclic aryl,
•halogenated carbocyclic aryl, and
•carbocyclic aryl substituted by C1-5 alkoxy.
In some embodiments of the present invention, R2 is -N(R2a)(R2b), wherein R2a is hydrogen or
C1-5 alkyl and R2b is C1-5 alkyl, C3-6 cycloalkyl, or Clo- alkyl substituted by substituent(s) independently
selected from the group consisting of:
•halogen,
•hydroxy,
•carboxy,

41
•carbamoyl,
•C1-5 alkoxy,
•amino,
•-NHBoc,
•C3-6 cycloalkyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C,_5 alkyl,
"C1-5 alkoxy, and
••-SO2NH2,
•heterocyclyl, and
C3-6 cycloalkyl, carbocyclic aryl, carbocyclic aryl substituted by substituent(s) independently
selected from the group consisting of:
•halogen,
•C1-5 alkyl,
"C1-5 alkoxy, and
•a group of Formula (V):

wherein Boc is carbamic acid tert-buty\ ester and G is C1-5 alkyl or C1-5 alkyl substituted by
substituent(s) independently selected from the group consisting of:
•carbocyclic aryl,
•halogenated carbocyclic aryl, and
•carbocyclic aryl substituted by C1-5 alkoxy.

42
In some embodiments of the present invention, R2 is -N(R2a)(R2b), wherein R2a is hydrogen or
C1-5 alkyl and R?b is C1-5 alkyl or C3-6 cycloalkyl.
In some embodiments of the present invention, R! is selected from the group consisting of:
(i) Ci-g alkyl, and
C|_8 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•halogen,
•oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•C1-5 alkylcarbonyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••nitro,
••C1-5 alkyl, and
'•C1-5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by C1-5 alkyl,
•Ci,5 alkoxycarbonyI,
*mono-C]o alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•mono-C],5 alkylamino substituted by carbocyclic aryl,
*di-C1-5 alkylamino,
•di-Q.5 alkylamino substituted by cyano,

43
•di-C1-5 alkylamino substituted by carbocyclic aryl,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•mono-carbocyclic arylamino substituted by C1-5 alkyl,
•di-carbocyclic arylamino,
•di-carbocyclic arylamino substituted by halogen,
•di-carbocyclic arylamino substituted by C1-5 alkyl,
•C1-5 alkoxycarbonylamino,
•carbocyclic arylcarbonylamino,
•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted C1-5 alkyl,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by substituent(s) independently selected from the
group consisting of:
'•carbocyclic aryl,
••carbocyclic aryl substituted by halogen, and
••carbocyclic aryl substituted by C1-5 alkoxy,
•carbocyclic arylthio,
•heterocyclylthio,
•heterocyclylthio substituted by nitro,
•heterocyclylthio substituted by C1-5 alkyl,
*C3-6 cycloalkyl,
•C3-6 cycloalkenyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
"halogen,
-C1-5 alkyl,

44
••C1-5 alkoxy,
"C2-5 alkenyl, and
•"C7-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and
•"carbocyclic aryl substituted by Cj.5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
—hydroxy,
**nitro,
••C1-5alky],
"C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
•••oxo,
—carbocyclic aryl, and
•••heterocyclyl,
••C2-5 alkenyl,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by halogen,
"C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryloxy,
••mono-carbocyclic arylaminocarbonyl,
••mono-carbocyclic arylaminocarbonyl substituted by halogen,
"di-carbocyclic arylaminocarbonyl,
••di-carbocyclic arylaminocarbonyl substituted by halogen,
••carbocyclic aryl, and

45
•"heterocyclyl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
"Cj-5 alkyl,
••C1-5 alkyl substituted by carbocyclic aryl,
••C1-5 alkoxy,
"C1-5 alkoxy substituted by carbocyclic aryl,
■•carbocyclic aryl, and
"carbocyclic aryl substituted by halogen,
(ii) C2-7 alkenyl, and
C2.7 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
—nitro, and
"C1-5 alkoxy,
(iii) C2-5 alkynyl, and
C2-5 alkynyl substituted by carbocyclic aryl,
(iv) C3.12 cycloalkyl, and
C3-12 cycloalkyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkyl,
•C1-5 alkyl substituted by oxo,
•C1-5 alkyl substituted by carbocyclic aryl, and
•carbocyclic aryl,

46
(v) carbocyclyl,
(vi) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
•carboxy,
•carbamoyl,
•C1-5O alky],
•Ci-io alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••hydroxy,
"OXO,
••carbocyclic aryloxy,
•'carbocyclic aryl, and
••carbocyclic aryl substituted by C1-5 alkyl,
•C1-7 alkoxy,
•C1-7 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••carbocyclic aryl, and
"halogenated carbocyclic aryl,
•C2-5 alkenyloxy,
•C3-6 cycloalkoxy,
•carbocyclic aryloxy,

47
•carbocyclic aryloxy substituted by nitro,
•carbocyclic aryloxy substituted by do alkoxy,
•d-5 alkoxycarbonyl,
•mono-C1-5 alkylaminocarbonyl,
"di-C1-5 alkyiaminocarbonyl,
•mono-C1-5 aikylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•amino,
•mono-d-5 alkylamino,
•di-C1-5 alkylamino,
•mono-d-5 alkylamino substituted by cyano,
•di-Cj.5 alkylamino substituted by cyano,
•C2-5 alkynylcarbonylamino,
"C2_5 alkynylcarbonylamino substituted by carbocyclic aryl,
•d-5 alkoxycarbonylamino,
•(carbocyclic aryl)NHC(O)NH,
'(carbocyclic aryl)NHC(O)NH substituted by d-5 alkoxy,
•(carbocyclic aryl)NHC(O)NH substituted by haloganated d-5 alkoxy,
•carbocyclic aryl azo,
•carbocyclic aryl azo substituted by mono-d-5 alkylamino,
•carbocyclic ary! azo substituted by di-do alkylamino,
•do- alkylthio,
"d-5 alkylthio substituted by halogen,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by nitro,
•carbocyclic arylthio substituted by cyano,
•aminosulfonyl,
•mono-d-5 alkytaminosulfonyl,

48
•di-C1-5 alkylaminosulfonyl,
•heterocyclylsulfonyl,
•C3-6 cycloalkyl,
•C3-6 cycloalkyl substituted by C1-5 alkyl,
•carbocyclic aryl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
"C1-5 alkyl,
"•carbocyclic aryl, and
••halogenated carbocyclic aryl,
(vii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•ammo,
•hydroxy,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••hydroxy,
••Cj.5 alkylthio,
"•C1-5 alkylthio substituted by carbocyclic aryl,
"C1-5 alkylthio substituted by halogenated carbocyclic aryl,
••carbocyclic aryl,
"carbocyclic aryl substituted by halogen, and

49
"heterocyclyl,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C\.5 alkyl,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-C1-5 alkylamino,
"di-C1-5 alkylamino,
•C1-5 alkylthio,
•C2.5 alkenylthio,
"carbocyclic arylthio,
'carbocyclic arylthio substituted by C^ alkoxycarbonyl,
•C[.5 alkylsulfonyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by C1-5 alkyl,
•C1-5 alkoxycarbonyl,
•C1-5 alkoxycarbonyl substituted by carbocyclic aryl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
••nitro,
••C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
•heterocyclyl;
wherein carbocyclic aryl is phenyl, naphthyl, or anthranyl;
carbocyclyl is 1,2,3,4-tetrahydronaphthyl, 1-oxo-indanyl, 9-fluorenyl,
9/f-fluorenyl, 9-oxo-9#-fluorenyl, adamantly, bicyclo[2.2.1]heptenyl,

50
bicyclo[2.2.3]heptyl, indanyl, indenyl, or menthyl;
heterocyclyl is 1,2,3-triazolyl, li/-indolyl, 1/J-pyrrolyl,
2,3-dihydro-l-oxo-isoindoIyI, 2,3-dihydro-benzo[l ,4]dioxinyl,
2,3-dihydro-benzofuryl, 2,4-dihydro-3-oxo-pyrazolyl, 2/f-benzopyranyJ,
2-oxo-benzopyranyl, 3,4-dihydro-2/f-benzo[b][l,4]dioxepinyl,
4,5,6,7-tetrahydro-benzo[b]thienyl, 4//-benzo[l,3]dioxinyl,
4-oxo-l,5,6,7-tetrahydro-indolyI, 4-oxo-benzopyranyl, 9#-carbazolyl, 9#-xanthenyl,
azetidinyl, benzo[l,3]dioxolyl, benzo[2,l,3]oxadiazolyl, benzo[l,2,5]oxadiazolyl,
benzo[2,l,3]thiadiazolyl, benzo[b]thienyl, benzofuryl, benzothiazolyl, furyl,
imidazo[2,l-b]thiazolyl, imidazolyl, isoxazolyl, morpholino, morpholinyl, oxazolyl,
phenanthro[9,10-d]oxazolyl, piperidyl, pyrazolyl, pyridyl, pyrimidyl, quinolyl,
quinoxalyl, tetrahydrofuryl, thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Q is Formula (il);
R] is selected from the group consisting of:
(i) Cj.g alkyl, and
Ci_8 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•halogen,
*oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•C1-5 alkylcarbonyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by nitro,
•heterocyclyloxy,

51
•heterocyclyloxy substituted by C1-5 alkyl,
•Ci_s alkoxycarbonyl,
•mono-C1-5 alkylaminocarbonyl,
•dI-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•mono-Cj.5 alkylamino substituted by carbocyclic aryl,
•di-Ci-s alkylamino,
•di-C1-5 alkylamino substituted by cyano,
*di-C1-5 alkylamino substituted by carbocyclic aryl,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
"C1-5 alkoxycarbonylamino,
•carbocyclic arylcarbonylamino,
•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted C1-5 alkyl,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by substituent(s) independently selected from the
group consisting of:
••carbocyclic aryl,
"carbocyclic aryl substituted by halogen, and
"carbocyclic aryl substituted by C1-5 alkoxy,
•carbocyclic arylthio,
•heterocyc ly Ithio,
•heterocyciylthio substituted by d_5 alkyl,
•C3-6 cycloalkyl,
•C3-6 cycloalkenyl,
•carbocyclyi,

52
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C1-5 alkyl,
••C1-5 alkoxy,
"C2-g alkenyl, and
"C2-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
—nitro,
••Cw alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
—oxo,
"••carbocyclic aryl, and
•••heterocyclyl,
••C2-5 alkenyl,
"C1-5 alkoxy,
"C1-5 alkoxy substituted by halogen,
"C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryloxy,
••mono-carbocyclic arylaminocarbonyl,

53
••mono-carbocyclic arylaminocarbony! substituted by halogen,
••di-carbocydic arylaminocarbony],
"di-carbocyclic arylaminocarbonyl substituted by halogen,
••carbocyclic aryl, and
—heterocyclyl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5 alkyl,
••C1-5 alkyl substituted by carbocyclic aryl,
•"C1-5 alkoxy,
••C1-5 alkoxy substituted by carbocyclic aryl,
"carbocyclic aryl, and
•■carbocyclic aryl substituted by halogen,
(ii) C7-7 alkenyl, and
C2-7 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
'carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
••nitro, and
••C1-5 alkoxy,
(iii) C2-5 alkynyl, and
C7.5 alkyny! substituted by carbocyclic aryl,
(iv) C3-6 cycloalky!, and
C3-6 cycloalkyl substituted by substituent(s) independently selected from the
group consisting of:

54
•C1-5 alkyl,
•C].g alky! substituted by oxo,
•C1-5 alkyl substituted by carbocyclic aryl, and
•carbocyclic aryl,
(v) carbocyciyl,
(vi) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•cyano,
"nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
"OXO,
"carbocyclic aryloxy,
"carbocyclic aryl, and
••carbocyclic aryl substituted by C1-5 alkyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••carbocyclic aryl, and
••halogenated carbocyclic ary],
•C2.5 alkenyloxy,
•C3^ eycloalkoxy,

55
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•C1-5 alkoxycarbonyI,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic ary!,
•di-Cj.5 alkylaminocarbonyl substituted by carbocyclic aryl,
•amino,
•mono-C1-5 alkylamino,
*di-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino substituted by cyano,
*C2.5 alkynylcarbonylamino,
■C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,
•(carbocyclic aryl)NHC(O)NH,
•(carbocyclic aryl)NHC(O)NH substituted by C1-5 alkoxy,
•(carbocyclic aryl)NHC(O)NH substituted by haloganated C1-5 alkoxy,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by halogen,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by cyano,
•mono-C1-5 alkylaminosulfonyl,
•di-C1-5 alkylaminosulfonyi, and
•carbocyclic ary],
(vii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,

56
•nitro,
•C1-5 alkyl,
•C].g alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••hydroxy,
••C1-5 alkylthio,
"C1-5 alkylthio substituted by carbocyclic aryl,
"C[.5 alkylthio substituted by halogenated carbocyclic aryl,
"carbocyclic aryl,
"carbocyclic aryl substituted by halogen, and
"heterocyclyl,
•C1-5 alkoxy,
'carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkyl,
•C1-5 alkylthio,
•C2-5 alkenylthio,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by Ct.5 alkoxycarbonyl,
•C1-5 alkylsulfonyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by C1-5 alkyl,
•C1-5 alkoxycarbonyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
••nitro,

57
—C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
•heterocyclyl;
R2 is methylamino or dimethylamino when Y is a single bond or -CH2-;
wherein carbocyclic aryl is phenyl, naphthyl, or anthranyl;
carbocyclyl is 1,2,3,4-tetrahydronaphthyI, 1-oxo-indanyl, 9-fluorenyI,
9-oxo-9//-fluorenyl, bicyclo[2.2.1]heptyl, indenyl, or menthyl;
heterocyclyl is 1,2,3-triazolyI, l//-indolyl, \H-pyno\y\,
2,3-dihydro-l-oxo-isoindolyl, 2,3-dihydro-benzo[l,4]dioxinyl,
2,3-dihydro-benzofiiryI, 2,4-dihydro-3-oxo-pyrazolyl, 2//-benzopyranyl,
2-oxo-benzopyranyl, 3,4-dihydro-2//-benzo[b][l,4]dioxepinyI, 4-oxo-benzopyranyl,
9//-carbazolyl, 9//-xanthenyl, azetidinyl, benzo[l,3]dioxolyl,
benzo[2,l,3]oxadiazolyl, benzo[l,2,5]oxadiazolyi, benzo[b]thienyl, benzofuryl,
benzothtazolyl, fiiryl, imidazo[2,l-b]thiazolyl, imidazolyl, isoxazolyl, morpholino,
pyrazolyl, pyridyl, pyrimidyl, quinolyl, quinoxalyl, thiazolyl, orthienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceuticalIy acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Rj is selected from the group consisting of:
(i) CUT alkyl, and
C[_7 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
*mono-C1-5 alkylamino,
*mono-C1-5 alkylamino substituted by substituent(s) independently selected
from the group consisting of:

58
••cyano, and
••carbocyclic aryl,
•di-C1-5 alkylamino,
•di-C1-5 alkylamino substituted by substituent(s) independently selected from
the group consisting of:
••cyano, and
"carbocyclic aryl,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted by C1-5 alkyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,
••C1-5 alkyl,
"C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
•••oxo, and
•••carbocyclic aryl,
"C1-5 alkoxy,
"C1-5 alkoxy substituted by halogen,
•heterocyclyl,
•heterocyclyl substituted by carbocyclic aryl, and
•heterocyclyl substituted by halogen,
(ii) C2.7 alkenyl, and
C2-7 alkenyl substituted by substituent(s) independently selected from the

59
group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by C1-5 alkoxy,
(iii) C2_5 alkynyl, and
C2_5 alkynyl substituted by carbocyclic aryl,
(iv) C3,6 cycloalkyl, and
C3-6 cycloalkyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkyl, and
•C1-5 alkyl substituted by carbocyclic aryl,
(v) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•cyano,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
"halogen, and
••carbocyclic aryl,
••carbocyclic aryl substituted by halogen,
•C2_5 alkenyloxy,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,

60
•di-C1-5 alkylamino substituted by cyano,
•C1-5 alkylthio, and
"C1-5 alkylthio substituted by halogen,
(vi) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
"C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
"hydroxy, and
••carbocyclic aryl,
•CN5 alkoxy,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by C1-5 alkoxycarbonyl,
•C1-5 alkoxycarbonyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
L is Formula (VII);
Y is a single bond or -CH2-;
R2 is methylamino or dimethylamino;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is l//-indolyl, l//-pyrrolyl, 2,3-dihydro-benzo[l,4]dioxinyl,
4-oxo-benzopyranyl, 9//-carbazoIyl, azetidinyl, benzo[l,3]dioxolyl, benzo[b]thienyl,

61
furyl, imidazo[2,l-b]thiazolyl, pyrazolyl, pyridyl, orthienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, p is 0; R3 and R4 are hydrogen; A is a single
bond or -CH2-; and B is a single bond or -CH2-; or a pharmaceutically acceptable salt, hydrate, or
solvate thereof.
In some embodiments of the present invention, R] is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•mono-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
*di-C]-5 alkylamino,
•di-C1-5 alkylamino substituted by cyano,
•mono-carbocyclic aryiamino,
•di-carbocyclic aryiamino,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
"C1-5 alkoxy,
•heterocyclyl, and
•heterocyclyl substituted by carbocyclic aryl,
(ii) C7-5 alkenyl, and
C2-5 alkenyl substituted by carbocyclic aryl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:

62
•halogen,
•hydroxy,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by halogen, and
•C2-5 alkenyloxy,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkyl,
•C1-5 alkyl substituted by carbocyclic aryl,
•C1-5 alkoxy, and
•C1-5 alkoxycarbonyl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is I/f-indolyl, azetidinyl, or benzo[l,3]dioxolyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
ethyl 4,6-dichloro-3-{[(cis-4-{[4-(dimethy!amino)quinolin-2-yl]amino}-cyC1-5hexyl)amino]-
methyl} -1 H-indoIe-2-carboxylate;
3-[{2-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-amino]ethyl}(phenyl)-
amino]propanenitrile;
N4,N4-dimethyl-N"-(cis-4-{[2-(2-phenyl-lH-indol-3-yl)ethyI]amino}-cyclohexyI)quinoline-2
,4-diamine;
N2-[cis-4-({[l-(diphenylmethyl)azetidin-3-yl]methyl}amino)cyclohexyl]-N4,N4-
dimethylquinoline-2,4-diamine;
N2-(cis-4-{[(2,6-dimethoxybenzyi)amino]methyl}cyC1-5hexyl)-N4,N4-dimethylquinoline-2,4-

63
diamine;
N2-(cis-4-{[(2-ethoxybenzyl)amino]methyI}cyclohexyl)-N4,N4-dimethylquinoline-2,4-
diamine;
N~-[cis-4-( {[(4-methoxy-1 -naphthyl)methy l]amino} methyl)cyclohexy 1]-N4,N4-
dimethylquinoline-2,4-diamine;
4-bromo-2-({[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-methyl]amino}-
methy I)-6-methoxypheno 1;
N"-[cis-4-({[(5-bromo-lH-indol-3-yl)methyl]amino}methyl)cyclohexyI]-N4,N4-
dimethylquinoline-2,4-diamine;
N~-(cis-4- {[(5-bromo-2,4-dimethoxybenzyl)amino] methyl} cyclohexyt)-N4,N4-
dimethylquinoline-2,4-diamine;
N2-(cis-4-{[(3,3-diphenyIprop-2-en-l-yl)amino]methyl}cyclohexyI)-N4,N4-
dimethylquinoline-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,6-trimethoxybenzyl)amino]methyl}-cyclohexyl)quinoline-2
,4-diamine;
N2-(cis-4-{[(2,5-diethoxybenzyl)amino]methyI}cyclohexyl)-N4,N4-dimethylquinoline-2,4-
diamine;
N2-(cis-4-{[(2,4-diethoxybenzyI)amino]methyl}cyC1-5hexyl)-N4,N4-dimethyIquinoline-2,4-
diamine;
N2-(cis-4-{[(3,5-dibromo-2-methoxybenzyl)amino]methyl}cyclohexyI)-N4,N4-
dimethy!quinoline-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-triethoxybenzy])amino]methyl}-cyclohexyl)quinoline-
2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-trimethoxybenzyI)amino]methyI}-cyC1-5hexyl)quinoline-2
,4-diamine;
N2-[cis-4-({[2-(allyloxy)benzyl]amino}methyl)cyclohexyl]-N4,N4-dimethylquinoline-2,4-
diamine;
N"-[cis-4-({[(7-methoxy-l,3-benzodioxol-5-yl)methyl]amino}methyl)-cyclohexy!]-N4,N4-

64
dimethylquinoline-2,4-diamine;
N2-{cis-4-[2-(4-bromo-2-trifluoromethoxy-phenyl)-ethylamino]-cyclohexyl}-N4,N4-
dimethyl-quinoline-2,4-diamine;
N"-[cis-4-(4-bromo-2-trifluoromethoxy-benzyl)amino-cyclohexyl]-N4,N4-dimethyI-quinoline
-2,4-diamine;
N"-[cis-4-(4-bromo-2-trifluoromethoxy-benzyl)amino-cyclohexyl]-N4-methyl-quinoline-2,4-
diamine;
N2-{4-[2-(4-bromo-2-trifluoromethoxy-phenyl)-ethylamino]-cyclohexyl}-N4-methyl-
quinoline-2,4-diamine;
N -methyl-N"-{cis-4-[(2-trifluoromethoxy-benzyl)amino-methyI]-cyC1-5hexyl}-quinoline-
2,4-diamine;
N -{cis-4-[(4-bromo-2-trifluoromethoxy-benzyI)amino-methyl]-cyclohexyl}'N4-methyl-
quinoline-2,4-diamine;
N2-{cis-4-[(4-bromo-2-trifluoromethoxy-benzyl)amino-methyI]-cyclohexyl}-N4,N4-
dimethyl-quinoline-2,4-diamine;
N4,N4-dimethyl-N2-{cis-4-[(2-trifluoromethoxy-benzyl)amino-methyl]-cyclohexyl}-
quinoline-2,4-diamine;
cis-N-(3,5~dimethoxybenzyl)-N'-(4'methylquinolin-2-yl)cyclohexane-l,4-diamine; and
cis-N-(3,5-dichlorobenzyl)-NL(4-methylquinoIin-2-yl)cyclohexane-l,4-diamine;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•hydroxy,
•oxo,
•C1-5 alkoxy,
•Ci_g alkoxy substituted by carbocyclic aryl,

65
*C1-5 alkylcarbonyloxy,
'carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••nitro,
"Cj.5 alkyl,
••C1-5 alkoxy, and
"C1-5 alkoxy substituted by halogen,
•heterocyclyloxy,
•heterocyclyloxy substituted by C1-5 alkyl,
•mono-C1-5 alky lam inocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylamino,
"di-C1-5 alkylamino,
•mono-carbocyclic arylamino,
*di-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•di-carbocyclic arylamino substituted by halogen,
•carbocyclic arylcarbonylamino,
'C1-5 alkoxycarbonylamino,
•C1-5 alkylthio,
•C1-5 alkytthio substituted by substituent(s) independently selected from the
group consisting of:
••carbocyclic aryl, and
"carbocyclic aryl substituted by substituent(s) independently
selected from the group consisting of:
•••halogen, and

66
"*C1-5 alkoxy,
•carbocyclic arylthio,
•heterocyclylthio,
•heterocyclylthio substituted by C1-5 alkyl,
•C3-6 cycloalkyl,
•C3-6 cycloalkenyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
"halogen,
••C1-5 aikyl,
"C1-5 alkoxy,
"C2.5 alkenyl, and
••C2-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•'•carbocyclic aryl, and
—carbocyclic aryl substituted by d_5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••nitro,
-d.5 alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
""OXO,
"•carbocyclic aryl, and

67
•••heterocyclyl,
"C1-5 alkoxy,
••C1-5 alkoxy substituted by halogen,
••C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryloxy,
••mono-carbocyclic arylaminocarbonyl,
••mono-carbocyclic arylaminocarbonyl substituted by halogen,
••di-carbocyclic arylaminocarbonyl,
••di-carbocyclic arylaminocarbonyl substituted by halogen,
"carbocyclic aryl, and
••heterocyclyl,
'heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
-C1-5 alky!,
"C1-5 alkyl substituted by carbocyclic aryl,
••C1-5 alkoxy,
"C1-5 alkoxy substituted by carbocyclic aryl,
"carbocyclic aryl, and
"carbocyclic aryl substituted by halogen,
(ii) C2-5 alkenyl, and
C2.5 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
"nitro,

68
(iii) C3-6 cycloalkyl, and
C3-6 cycloaiky] substituted by substituent(s) independently selected from the
group consisting of:
•C,_5 aikyl,
•Cj.5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•■oxo, and
••carbocyclic aryl, and
•carbocyclic aryl,
(iv) carbocyclyl,
(v) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
•carboxy,
•carbamoyl,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••hydroxy,
••oxo,
••carbocyclic aryloxy,
"•carbocyclic aryl, and
••carbocyclic aryl substituted by C1-5 alkyl,

69
•Cj_5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
"halogen, and
••carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•C1-5 alkoxycarbonyl,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•amino,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•C2-5 alkynylcarbonylamino,
•C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,
•(carbocyclic aryl)NHC(O)NH,
•(carbocyclic aryl)NHC(O)NH substituted by C1-5 alkoxy,
•(carbocyclic aryl)NHC(O)NH substituted by haloganated C1-5 alkoxy,
•C,_s alkylthio,
•C1-5 alkylthio substituted by halogen,
•carbocyclic arylthio,
•carbocyctic arylthio substituted by cyano,
•mono-C1-5 alky lam inosulfonyl,
•di-C1-5 alkylaminosulfonyl, and
•carbocyclic aryl,
(vi) heterocyclyl, and

70
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•hydroxy,
•amino,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C1-5 alkylthio,
••C1-5 alkylthio substituted by carbocyclic aryl,
"C1-5 alkylthio substituted by halogenated carbocyclic aryl,
"•carbocyclic aryl,
"carbocyclic aryl substituted by halogen, and
••heterocyclyl,
*Ci^ alkoxy,
•carbocyclic aryloxy,
'carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C1-5 alkyl,
•carbocyclic aryioxy substituted by C1-5 alkoxy,
•mono-C1-5 alkylamtno,
•di-C1-5 alkylamino,
*Ct-5 alkylthio,
•C2-5 alkenylthio,
•carbocyclic arylthio,
•C1-5 alkylsulfonyl,
'carbocyclic arylsulfonyl,

71
•carbocyclic arylsulfonyl substituted by C1-5 alkyl,
•carbocyclic aryl.,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
-C1-5 alkyl,
•heterocyclyl;
L is Formula (VII);
Y is -C(O)-;
wherein carbocyclic aryl is phenyl, naphthyl, or anthranyl;
carbocyclyl is 1,2,3,4-tetrahydronaphthyl, 1-oxo-indanyl,
9-oxo-9if-fluorenyl, or indenyl;
heterocyclyl is 1,2,3-triazolyl, \H-'mdo\y\, l//-pyrrolyl,
2,3-dihydro-l-oxo-isoindoIyl, 2,3-dihydro-benzofiiryI, 2,4-dihydro-3-oxo-pyrazolyl,
2#-benzopyranyl, 2-oxo-benzopyranyl, 9//-xanthenyl, benzo[l,3]dioxolyl,
benzo[2,l,3]oxadiazolyl,benzo[l,2,5]oxadiazolyl,benzo[b]thienyl, benzofuryl,
benzothiazolyl, furyl, imidazolyl, isoxazolyl, morpholino, pyrazolyl, pyridyl,
pyrimidyl, quinolyl, quinoxalyl,thiazolyl, orthienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R2 is hydrogen, halogen, methyl,
trifluoromethyl, methoxy, carbamoyl, amino, methylamino, or dimethylamino; p is 0; R3 and R4 are
hydrogen; A is a single bond; B is a single bond or -CH2-; or a pharmaceutically acceptable salt,
hydrate, or solvate thereof.
In some embodiments of the present invention, R] is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the group

72
consisting of:
•oxo,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C1-5 alkyl,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-C1-5 alkylamino,
"di-C1-5 alkylamino,
•mono-carbocyclic arylamino,
•di-carbocydic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•di-carbocyclic arylamino substituted by halogen,
•C3-6 cycloalkyl,
•carbocyciic aryl,
•carbocyclic aryl by substituent(s) independently selected from the group
consisting of:
••halogen,
••Cj.s alkyl, and
••C1-5 alkoxy,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5 alkyl,
••C1-5 alkoxy, and
••carbocyclic aryl,
(ii) C2-5 alkenyl, and
C2_5 alkenyl substituted by substituent(s) independently selected from the
group consisting of:

73
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
••nitro,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
carbamoyl,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
C1-5 alkyl substituted by hydroxy,
•C1-5 alkoxycarbonyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••carbocyclic aryl,
•carbocyclic aryloxy, and
'carbocyclic aryloxy substituted by C1-5 alkoxy,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,

74
* nitro,
•amino,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
*C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by Q.g alkyl,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•carbocyclic aryl,
•carbocyclic aryl substituted by halogen,
'carbocyclic aryl substituted by nitro, and
•heterocyclyl;
wherein carbocyclic aryl is phenyl;
heterocyclyl is 1,2,3-triazolyl, 1/f-indolyl, l#-pyrrolyl, 9#-xanthenyI,
benzo[2,l,3]oxadiazolyl, benzo[l,2,5]oxadiazoryl, furyl, isoxazolyl, pyridyl,
quinolyl, quinoxalyl, thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
'carbocyclic aryloxy,
'carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C1-5 alkyl,

75
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-Ci,5 alkylamino,
*di-Ci_g alkylamino,
•mono-carbocyclic arylamino.,
•di-carbocyclic arylamino,
•mono-carbocyclic aryiamino substituted by halogen,
•di-carbocyclic arylamino substituted by halogen,
•carbocyclic aryl,
•carbocyclic aryl by substituent(s) independently selected from the group
consisting of:
••halogen,
••C1-5 a'kyl, and
••C1-5 alkoxy,
and
•heterocyclyl,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•hydroxy,
•cyano,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxycarbonyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by halogen,
•carbocyclic aryloxy, and

76
•carbocyclic aryloxy substituted by C1-5 alkoxy,
(iii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alky],
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
"carbocyclic aryloxy substituted by C1-5 alkyl,
"carbocyclic aryloxy substituted by C1-5 alkoxy,
•carbocyclic aryl,
•carbocyclic aryl substituted by halogen,
•carbocyclic aryl substituted by nitro, and
•heterocyclyl;
wherein carbocyclic aryl is phenyl;
heterocyclyl is li/-indolyl, l//-pyrrolyl, 9/f-xanthenyl,
benzo[2,I,3]oxadiazolyl, benzo[l,2,5]oxadiazolyl, furyl, isoxazolyl, pyridyl,
thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-3-methoxybenzamide;
3-bromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]aniino}cyclohexyl)-benzamide;
4-bromo-N-{cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-benzamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2?l,3-benzoxadiazole-5-
carboxamide;

77
3-chloro-N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-benzamide;
4-chloro-N-(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}cyclohexyI)-benzamide;
4'ChIoro-N-(cis-4-{[4-(dimethylamino)quinoiin-2-yI]amino}cyclohexyl)-3-niIrobenzamide;
3-cyano-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexy])-benzamide;
3,5-dichloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyC1-5hexy])benzamide;
3,4-dichloro-N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}-cyC1-5hexyI)benzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-2,2-diphenylacetamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-3,4-difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3,5-difluorobenzamide;
N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexyl)-4-fluorobenzamide;
N-(cis-4-{[4-(dimethylatnino)quinolin-2-yl]amino}cyclohexyl)-3-fluoro-5-
(trifluoromethyl)benzam ide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-methyl-3-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-y!]amino}cyclohexyl)-2-phenoxybutanamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-phenoxypropanamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-methylbenzamide;
N'(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-3-(trifluoromethoxy)-
benzamide;
4-bromo-N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-3-
methylbenzamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-3-iodobenzamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2,4-
difluorobenzam ide;
N-(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}cyclohexyI)-2,5-dimethyI-3-furamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-4-fIuorobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyC1-5hexyl)-3-fluoro-4-
methylbenzamide;

78
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-3,5-dimethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3,5-bis(trifluoromethy])-
benzamide;
(2E)-N-(cis-4-{[4-{dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-3-(4-nitrophenyl)-
acrylamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yI]amino}cyclohexyl)-4-fluoro-3-
methy lbenzam ide;
2,5-dichloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)thiophene-3-
carboxamide;
2-(4-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}-cyclohexyl)-
acetamide;
3-(2-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)-5-
methyIisoxazole-4-carboxamide;
l-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)-
cyclopentanecarboxamide;
3-(2-chloro-6-fluorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
5-methylisoxazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-fluorobenzamtde;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-fluoro-3-
(trifluoromethy l)benzam ide;
N-(cis-4-{[4-(dimetbylamino)quinolin-2-yl]amino}cyclohexyl)-5-methyl-2-phenyl-2H-
1,2,3-triazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-(4-methoxyphenoxy)-5-nit
robenzamide;
N-(cis-4-{[4-(dimethylatnino)quinolin-2-yI]amino}cyclohexyl)-5-nitro-2-furamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-phenoxyacetamide;
N-(cis-4-{[4-(dimethy!amino)quinolin-2-yl]amino}cyclohexyl)quinoxaline-2-carboxamide;
2-(3-chIorophenoxy)-N-(cis-4-{[4-(dimethy]amino)quinoIin-2-y]]amino}-cyclohexyl)-

79
acetamide;
3-(2,6-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyC1-5hexyl)-5-
methy 1 isoxazole-4-c arboxam i de;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyc!ohexyl)-2-phenoxynicotinamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yI]amino}cyC1-5hexyI)-2-{4-methylphenoxy)-
nicotinamide;
N-(cis-4-{[4-(dimethylamino)quinoiin"2~yl]amino}cyclohexyl)-2-(2-thienyi)-l,3-thiazole-4-
c arboxam ide;
5-bromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-thiophene-2-
carboxamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-2-(2,3,6-trichlorophenyl)-
acetamide;
5-(4-chloro-2-nitrophenyI)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2
-furamide;
5-chloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-thiophene-2-
carboxamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yi]amino}cyclohexyl)-5-iodo-2-ftiramide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-(2-iodophenyl)acetamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-(5-methoxy-2-methyl-lH-i
ndol-3-yl)acetamide;
(2E)-N-(cis-4-{[4-(dimethyIamino)quinoIin-2-yl]amino}cyclohexyl)-3-(3-nitrophenyl)-
acrylamide;
2,2-bis(4-chIorophenyl)-N-(cis-4-{[4-(dimethy]amino)quinolin-2-yl]-amino}cyC1-5hexyI)-
acetamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyC1-5hexyl)-5-nitrothiophene-2-
carboxamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-3-methyl-4-nitrobenzamide;
N-(cis-4-{[4-(dimethyIamino)quinoIin-2-yI]amino}cyclohexyl)-3-methoxy-4-

80
nitrobenzamide;
5-bromo-N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-furamide;
4,5-dibromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)thiophene-2-
carboxamide;
4,5-dibromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)-2-furamide;
N-(cis-4-{[4-(dimethylamino)quinoIin~2-yl]amino}cyclohexyI)-2-(lH-indol-3-yt)acetamide;
N-(cis~4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-(lH-indol-3-yl)-4-oxo-4-p
henylbutanamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-(2-phenyl-lH-indol-3-
yl)acetamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-(2,4,6-trichlorophenoxy)-a
cetamide;
3-(ben2yloxy)-N-(cis-4-{[4-(dimethylamino)quinolin-2'yl]amino}-cyclohexyl)-4-
methoxybenzamide;
N-(cis-4- {[4-(dimethylamino)quino!in-2-yl]amino} cyclohexyl)-2-phenoxybenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-2-phenylquinoline-4-
carboxamide;
N-(cis-4'{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-5-(3-nitrophenyl)-2-
fiiramide;
N-(cis-4'{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-5-nitrothiophene-3-
carboxamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-l-methyl-4-nitro-lH-
pyrrole-2-carboxamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-4-nitrobenzamide;
N-(cis-4-{[4-{dimethylamino)quinotin-2-yl]amino}cyclohexyl)-2-methoxy-4-
nitrobenzaraide;
N-(cis-4- {[4-(dimethy lamino)quinolin-2-yl]amino} cyclohexyl)-3-fluoro-4-
(trifluoromethyl)benzamide;

81
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3,5-dimethyl-4-
nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-2-mesityi-2-oxoacetamide;
5-chloro-N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexyI)-2-
hy droxybenzam ide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}cyclohexyl)methyl]-3-
methoxybenzamide;
3-bromo-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-methyl]-
benzamide;
4-bromo-N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-methyl]-
benzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-2,l,3-
benzoxadiazole-5-carboxamide;
3-chloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-methyI]-
benzamide;
4-chloro-N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-methyl]-
benzamide;
4-chloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-methyl]-3-
nitrobenzamide;
3-cyano-N-[(cis-4-{[4-(dimethylamino)quinoiin-2-yl]amino}cyclohexyI)-methyl]benzamide;
3,5-dich]oro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)methyl]-
benzamide;
3,4-dichloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)methyl]-
benzamide;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)methyl]-2,2-
diphenylacetamide;
N-[(cis-4-{[4-(dimethylamino)quino!in-2-yl]amino}cyclohexyl)methyl]-3,4-
d ifluorobenzamide;

82
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyI]-3,5-
difluorobenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-4-fluorobenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-3-fluoro-5-
(trifluoromethyl)benzamide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}cyC1-5hexyl)methyl]-4-methyl-3-
nitrobenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-3-nitrobenzamide;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)methyl]-2-
phenoxybutanamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-2-
phenoxypropanamide;
N- [(c is-4- {[4-(dimethy lamino)qu inolin-2-y 1] amino} cy clohexy I)methy 1] -3 -
methy lbenzam i de;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)methyl]-3-
(trifluoromethoxy)benzamide;
4-bromo-N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyC1-5hexyl)-methyl]-3-
methy lbenzam ide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)methyl]-3-iodobenzamide;
3-chloro-N-[(cis-4-{[4-(dimethylamino)quinoiin-2-yI]amino}cyclohexyl)-methyl]-2,4'
difluorobenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)methyl]-2,5-dimethyl-3-
furamide;
3-chloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyc]ohexyl)-methyl]-4-
fluorobenzamide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)methyl]-3-fluoro-4-
methylbenzamide;
N-[(cis-4-{[4-(dimethyIamino)quinoIin-2-yI]amino}cyC1-5hexyl)methyl]-3,5-

83
dimethoxybenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)methyl]-3,5-
bis(trifluoromethyl)benzamide;
(2E)-N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyC1-5hexyI)-methyl]-3-(4-
nitrophenyl)acrylamide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)methyl]-4-fluoro-3-
methylbenzamide;
2,5-dichloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-y]]amino}-cyclohexyl)methyl]-
thiophene-3-carboxamide;
2,6-dichloro-N-[(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} -cyclohexyl)methy 1]-
benzamide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)methyI]-2,4,6-
tr imethy 1 ben zam ide;
2,4,6-trichloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)methyl]-
benzamide;
(2E)-3-(2-chlorophenyl)-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-
methyl]acrylamide;
5-bromo-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-methyl]thiophene-
2-carboxamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methy!]-2-(2)3,6-
trichlorophenyl)acetamide;
5-(4-chloro-2-nitrophenyl)-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)methyl]-2-furamide;
5-chloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-methyl]thiophene-
2-carboxamide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}cyclohexyl)methyl]-5-iodo-2-furamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-2-(2-iodophenyl)-
acetamide;

84
(2E)-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-methyl]-3-(3-
nitrophenyt)acrylamide;
2,2-bis(4-chlorophenyl)-N-[(cis-4-{[4-(dimethylamino)quinoiin-2-yl]amino}cyclohexyI)-
methyl]acetamide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-y!]amino}cyclohexyI)methyI]-5-nitrothiophene-2-
carboxamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyc!ohexyl)methyl]-3-methy]-4-
nitrobenzamide;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)methyl]-3-methoxy-4-
nitrobenzamide;
N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyclohexyI]-2-phenoxy-nicotinamide;
3,4-difluoro-N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyl]-benzamide;
3,4-difluoro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
2-phenoxy-N- [cis-4-(quinol in-2-ylam ino)-cy c I ohexy I] -n icotin ami de;
3-chloro-N-[cis-4-(4-methyl-quinoiin-2-ylamino)-cyclohexyI]-benzamide;
N-[cis-4-(4-chloro-quinolin-2-ylamino)-cyclohexyl]-2-phenoxy-nicotinamide;
3-methyI-N-[cis-4-(quinolin-2-ylamino)-cyclohexyI]-benzamide;
3-methoxy-N-[cis-4-(quinolin-2-ylamino)-cyC1-5hexyl]-benzamide;
3-chloro-N-[cis-4-(quinoIin-2-y!amino)-cyC1-5hexyl]-benzamide;
5-nitro-thiophene-3-carboxylicacid [cis-4-(quinolin-2-ylamino)-cyclohexyl]-amide;
5-nitro-thiophene-3-carboxylicacid [cis-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-amide;
3-chloro-4-fluoro-N-[cis-4-(quinoiin-2-ylamino)-cyclohexyl]-benzamide;
3,5-dimethoxy-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
3,4-dichloro-N-[cis-4-(quinolin-2-ylamino)-cyC1-5hexyl]-benzamide;
benzo[2,3,l]oxadiazole-5-carboxylic acid [cis-4-(quino!in-2-ylamino)-cyclohexyl]-amide;
3-methyl-N-[cis-4-(4-methyi-quinolin-2-yiamino)-cyclohexy]]-benzamide;
3-methoxy-N-[cis-4-(4-methyi-quinoIin-2-y]amino)-cyclohexyl]-benzamide;

85
4-cyano-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-benzamide;
l-methyI-4-nitro-IH-pyrroIe-2-carboxyiic acid [cis-4-(quinolin-2-ylamino)-
cyclohexyl]-amide;
9H-xanthene-9-carboxylic acid [cis-4-(quinolin-2-ylamino)-cyclohexylj-amide;
5-(4-chloro-phenyl)-furan-2-carboxylic acid [cis-4-(quinolin-2-yIamino)-cyclohexyl]-amide;
3-nitro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
4-fluoro-3-methyl-N-[cis-4-(quinolin-2-yIamino)-cyclohexy]]-benzamide;
3-bromo-N-[cis-4-(quinolin-2-yIamino)-cyclohexyl]-benzamide;
2-(2-bromo-phenoxy)-N-[cis-4-(quinolin-2-yIamino)-cyclohexyl]-nicotinamide;
3-cyano-N-[cis-4-(quinoIin-2-ylamino)-cyC1-5hexyI]-benzamide;
N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-trifluoromethyl-benzamide;
N-[cis-4-(4-chloro-quinolin-2-ylamino)-cyclohexyl]-3,4-difluoro-benzamide;
3,4-dichloro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3-chloro-4-fluoro-N-[cis-4-(4-methyl-quino!in-2-ylamino)-cyclohexyl]-benzamide;
4-fluoro-3-methyl-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
l-methyl-4-nitro-lH-pyrrole-2-carboxylicacid [cis-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-amide;
9H-xanthene-9-carboxylic acid [cis-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyl]-amide;
5-bromo-fliran-2-carboxyiic acid [cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-amide;
N-[cis-4-(4-methyI-quinolin-2-yIamino)-cyclohexyI]-2-m-tolyIoxy-acetamide;
N-[cis-4-(quinoIin-2-ylamino)-cyclohexyI]-2-m-tolyloxy-acetamide;
2,2-diphenyl-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide;
5-brotno-furan-2-carboxylic acid [cis-4-(quinolin-2-ylamino)-cyclohexyl]-amide;
benzo[2,3,l]oxadiazo!e-5-carboxylic acid [cis-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-amide;
3-bromo-N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyl]-benzamide;
3-cyano-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyC1-5hexy]]-3-trifluoromethyl-benzamide;

86
N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyl]-2,2-diphenyl-acetamide;
2-(4-fluoro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-fluoro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-y!amino)-cyC1-5hexyl]-nicotinamide;
2-(3,4-difluoro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(3,4-difluoro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
nicotinamide;
N-[cis-4-(quinoIin-2-ylamino)-cyclohexyl]-2-/?-tolyloxy-nicotinamide;
N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-2~p-toIyloxy-nicotinamide;
2-(4-chloro-phenoxy)-N-[cis-4-(quinolin-2-yIamino)-cyclohexyl]-nicotinamide;
2-(4-chloro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-bromo-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-bromo-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-methoxy-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-methoxy-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(3-chloro-4-fIuoro-phenoxy)-N-[cis-4-(quinoIin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(3-chloro-4-fluoro-phenoxy)-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-
nicotinamide;
N-[cis-4-(quinolin-2-ylamino)-cyC1-5hexyl]-2-m-tolyloxy-nicotinamide;
N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyC1-5hexyl]-2-w-tolyloxy-nicotinamide;
2-(3-methoxy-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-acetamide;
2-(3-chloro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyclohexyl]-acetamide;
2-(3-chloro-4-fluoro-phenoxy)-N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyl]-
acetamide;
2-(3,4-dichloro~phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-acetamide;
C-(methyl-pheny]-amino)-N-[cis-4-(4-methyl-quinoIin-2-yIamino)-cyclohexyl]-acetamide;
2-(3,4-dichloro-phenylamino)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-
acetamide;
2-(3-methoxy-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide;

87
2-(3-chloro-phenoxy)-N-[cis-4-(quinoIin-2-ylamino)-cyclohexyl]-acetamide;
2-(3-chIoro-4-fluoro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide;
2-(3,4-dichloro-phenoxy)-N-[cis-4-(quinolin-2-yIamino)-cyclohexyl]-acetamide;
C-(methy!-phenyl-amino)-N-[cis-4-(quinolin-2-ylamino)-cyC1-5hexyl]-acetamide;
2-(3,4-dichIoro-phenylamino)-N-[cis-4-(quinoIin-2-ylaraino)-cyclohexyl]-acetamide;
3-hydroxy-N-[cis-4-(quinolin-2-y!amino)-cyclohexyl]-benzamide;
N-[cis-4-(quinolin-2-ylamino)-cyclohexyI]-isophthalamic acid methyl ester;
N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-3-trifluoromethoxy-benzamide;
N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-bis-trifluoromethyl-benzamide;
N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-3-trifluoromethoxy-benzamide;
N-[cis-4-(4-amino-quinoIin-2-ylamino)-cyclohexyl]-3,4-difluoro-benzamide;
C-(ethyl-phenyl-amino)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide;
C-(ethyl-phenyl-amino)-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-acetamide;
3-hydroxy-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-benzamide;
2-amino-N~[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2,3-difluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
2,4-difluoro-N-[cis-4-(4-methyl-quinolin-2-y!amino)-cyclohexyl]-benzamide;
2,5-difluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
2,6-difluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3,5-difluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
C-[(4-chloro-phenyt)-ethyl-amino]-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
acetamide;
4-chIoro-3-fluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
4-fluoro-N-[cis-4-(4-methyl-quino!in-2-yIamino)-cyclohexyl]-benzamide;
3-fIuoro-N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyc]ohexyl]-benzamide;
2-fluoro-N-[cis-4-(4-methyl-quinoIin-2-y]amino)-cyclohexyl]-benzamide;
4-chIoro-N-[cis-4-(4-methyt-quinoIin-2-ylamino)-cyclohexyl]-benzamide;
N-[cis-4-(4-methyi-quinolin-2-ylamino)-cyclohexyl]-isophthalamic acid methyl ester;

3,5-difluoro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
4-chloro-3-fluoro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
C-[(4-chloro-phenyI)-ethyi-amino]-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide;
6-chIoro-N-[cis-4-(4-methyI-quinoIin-2-ylamino)-cyclohexyl]-nicotinamide;
6-dimethylamino-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
3-hydroxymethyI-N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyc]ohexyl]-benzamide;
N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-isophthalamide;
3-chloro-5-fluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3,4,5-trifluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
pyridine-2-carboxylic acid [cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-amide;
4-chloro-pyridine-2-carboxylic acid [cis-4-(4-methyl-quinoIin-2-ylamino)-
cyclohexyl]-amide;
5-bromo-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyclohexyl]-6-trifluoromethyI-nicotinamide;
3,4-difluoro-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexylmethyl]-benzamide;
N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexylmethyl]-2-phenoxy-nicotinamide;
N-[cis-4-(4-dimethyIamino-quinolin-2-ylamino)-cyclohexylmethyl]-3,4-difluoro-benzamide;
3,4-difluoro-N-[cis-4-(quinoHn-2-ylamino)-cyclohexylniethyI]-benzamide;
2-phenoxy-N-[cis-4-(quinolin-2-ylamino)-cyclohexylmethyl]-nicotinamide;
4-methyl-N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}benzamide;
2-(4-chlorophenoxy)-N-{cis-4-[(4-methyJquinolin-2-yl)amino]cyclohexyl}acetamide;
3,4,5-trimethoxy-N-{cis-4-[(4-methyIquinolin-2-yl)amino]cyclohexyI}benzamide;
2-(3,4-difluorophenyI)~N-{cis-4-[(4-methyiquinolin-2-yl)amino]cyclohexyl}acetamide;
2-(2-bromo-4?5-dimethoxyphenyl)-N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyi}-
acetamide;
2,6-dimethoxy-N'{cis-4-[(4-methyIquinolin-2-yl)amino]cyclohexyl}nicotinamide;
N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}-4-(trifluoromethoxy)benzamide;
5-chloro-N-[cis~4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-nicotinamide; and

89
5-fluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
3-bromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-benzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2,l,3-benzoxadiazole-5-
carboxamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-benzamide;
4-chIoro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-ben2amide;
4-chloro-N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-3-nitrobenzamide;
3,4-dtchloro-N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}-cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-3,4-difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-fluorobenzamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-3-nitrobenzamide;
N-(cis~4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-phenoxybutanamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-2-phenoxypropanamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-methylbenzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-
methylbenzamide;
N-(cis-4-{[4-(dimethyIamino)qumolin-2-yl]amino}cyclohexyl)-2,5-dimethyl-3-ruramide;
3-chIoro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3,5-dimethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)quinoiin-2-yl]amino}cyclohexyl)-4-fluoro-3-
methylbenzamide;
2-(4-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)-
acetamide;
3-(2-chlorophenyl)-N-(cis-4-{[4-(dimethyiamino)quinolin-2-yl]amino}-cyclohexyl)-5-
methylisoxazole-4-carboxamide;

90
3-(2-chloro-6-fluorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
5-methylisoxazoie-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)quino]in-2-yl]amino}cyclohexyl)-4-fluoro-3-
(trifluoromethyl)benzamide;
N-(cis-4- {[4-(dimethyIamino)quinolin-2-y ljamino} cyclohexy l)-2-(4-methoxyphenoxy)-5-
nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-5-nitro-2-furamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-phenoxyacetamide;
2-(3-chIorophenoxy)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyC1-5hexyl)-
acetamide;
3-(2,6-dichIorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)-5-
methylisoxazoIe-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-phenoxynicotinamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-y!]amino}cyC1-5hexyl)-2-(4-methylphenoxy)-
nicotinamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-2-(2-thienyl)-l,3-thiazole-4-
carboxamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-t2,3,6-trichlorophenyl)-
acetamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-5-iodo-2-furamide;
N-(cis-4-{[4-(dimethyIamino)quinoIin-2-yI]ammo}cyclohexyl)-5-nitrothiophene-2-
carboxaraide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-methyI-4-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-methoxy-4-
nitrobenzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-furamide;
4,5-dibromo-N-(cis-4-{[4-(dimethy!amino)quinolin-2-yl]amino}-cyclohexyl)-2-furamide;
N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-2-(lH-indol-3-yI)acetamide;

91
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-5-(3-nitrophenyl)-2-
furamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-5-nitrothiophene-3-
carboxamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-l-methyi-4-nitro-lH-
pyrrole-2 -c arboxam ide;
N-(cis-4-{[4-(diraethylamino)quinolin-2-yl]amino}cyclohexyI)-4-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyC1-5hexyI)-3-fluoro-4-
(trifluoromethyljbenzamide;
3-bromo-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-methyl]-
benzamide;
N-[(cis-4- {[4-(dimethyIamino)quinoIin-2-yl]amino} cyc!ohexyI)methyI]-2,1,3-
benzoxadiazole-5-carboxamide;
3-chloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-methyl]-
benzamide;
4-chloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-methyl]-
benzamide;
4-chloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-methyI]-3-
nitrobenzamide;
3,4-dichloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyI)methyl]-
benzamide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)methyl]-3,4-
difluorobenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)methyl]-4-fluorobenzamide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyC1-5hexyI)methyl]-3-nitrobenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-2-
phenoxybutanamide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}cyclohexyl)methyl]-2-

93
3,4-difluoro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
2-phenoxy-N-[cis-4-(quinolin~2-ylamino)-cyclohexyl]-nicotinamide;
3-chloro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-benzamide;
3-methyl-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
3-methoxy-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
3-chloro-N-[cis-4-(quinolin-2-ylamino)-cycJohexyl]-benzamide;
5-nitrothiophene-3-carboxyIic acid [cis-4-(quinolin-2-ylamino)-cyclohexyI]-amide;
5-nitro-thiophene-3-carboxylic acid [cis-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-amide;
3-chIoro-4-fluoro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
3,5-dimethoxy-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
3,4-dichIoro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
benzo[2J3,l]oxadiazole-5-carboxylic acid [cis-4-(quinolin-2-ylamino)-cyclohexyl]-amide;
3-methyI-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-benzamide;
3-methoxy-N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyclohexyl]-benzamide;
4-cyano-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-benzamide;
l-methyl-4-nitro-lH-pyrrole-2-carboxylicacid [cis-4-(quinolin-2-ylamino)-
cyclohexyl]-amide;
9H-xanthene-9-carboxylic acid [cis-4-(quinolin-2-ylamino)-cyclohexyl]-amide;
3-nitro-N-[cis-4-(quinoIin-2-ylamino)-cyC1-5hexy!]-benzamide;
4-fluoro-3-methyl-N~[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
3-bromo-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
2-(2-bromo-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
3-cyano-N-[cis-4-(quinoIin-2-yIamino)-cyclohexyI]-benzamide;
N-[cis-4-(quinolin-2-ylamino)-cyC1-5hexyl]-trifluoromethyI-benzamide;
N-[cis-4-(4-ch!oro-quinolin-2-ylamino)-cyC1-5hexyl]-3,4-difluoro-benzamide;
3,4-dichloro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3-chIoro-4-fIuoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;

94
4-fluoro-3-methyl-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
l-methyl"4-nitro-lH-pyrrole-2-carboxylic acid [cis-4-(4-methyI-quinolin-2-ylamino)-
cyclohexyl]-amide;
9H-xanthene-9-carboxylic acid [cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-amide;
5-bromo-furan-2-carboxyIic acid [cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-amide;
N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyl]-2-m-tolyloxy-acetamide;
N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-2-m-toIyloxy-acetamide;
2,2-diphenyl-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide;
5-bromo-furan-2-carboxylic acid [cis-4-(quinolin-2-ylamino)-cyclohexyl]-amide;
benzo[2,3,l]oxadiazole-5-carboxylic acid [cis-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-amide;
3-bromo-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3-cyano-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-benzamide;
N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-3-trifluoromethyl-benzamide;
N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyC1-5hexyl]-2,2-diphenyl-acetamide;
2-(4-fluoro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-fluoro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(3,4-difluoro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(3,4-difIuoro-phenoxy)-N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyI]-
nicotinamide;
N-[cis-4-(quinolin-2-yIamino)-cyclohexyl]-2-/'-tolyloxy-nicotinainide;
N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-2-p-tolyloxy-nicotinamide;
2-(4-chloro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-chIoro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-bromo-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-bromo-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-methoxy-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-methoxy-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide;

95
2-(3-chloro-4-fluoro-phenoxy)-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-
nicotinamide;
N-[cis-4-(qutnolin-2-ylamino)-cyclohexyl]-2-m-tolyloxy-nicotinamide;
N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-2-w-tolyloxy-nicotinamide;
2-(3-methoxy-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-acetamide;
2-(3-chloro-phenoxy)-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyC1-5hexyl]-acetamide;
2-(3-chloro-4-fluoro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-
acetamide;
2-(3,4-dichloro-phenoxy)-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-acetamide;
C-(methyl-phenyl-amino)-N-[cis-4-(4-methyl-quinolin-2-yl am ino)-cyclohexyl]-acetamide;
2-(3-methoxy-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyC1-5hexyl]-acetamide;
2-(3-chloro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyC1-5hexyl]-acetamide;
2-(3-chloro-4-fluoro-phenoxy)-N-[cis-4-(quinoIin-2-ylamino)-cyclohexyl]-acetamide;
2-(3,4-dichIoro-phenoxy)-N-[cis-4-(quinolin~2-ylamino)-cyclohexyl]-acetamide;
C-(methyl-phenyl-amino)-N-[cis-4-(quinolin-2-yIamino)-cyC1-5hexyl]-acetamide;
N-[cis-4~(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-3-trifluoromethoxy-benzamide;
N-[cis-4-(4-amino-quinolin-2-ylamino)-cyclohexyl]-3,4-difluoro-benzamide;
C-(ethyl-phenyl-amino)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide;
C-(ethyl~phenyl-amino)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexy I]-acetamide;
3-hydroxy-N-[cis-4-(4-methyI-quinoIin-2-yIamino)-cyclohexyl]-benzamide;
2,4-difluoro-N-[cis-4-(4~methyl-quinoIin-2-yIamino)-cyclohexyl]-benzamide;
3,5-difluoro-N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyl]-benzamide;
C-[(4-chloro-phenyl)-ethyl-amino]-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
acetamide;
4-chloro-3-fluoro-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyC1-5hexyl]-benzamide;
4-fluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3-fluoro-N-[cis-4-(4-methyl-quinolin-2-y]amino)-cyclohexy!]-benzamide;
4-chloro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;

96
N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-isophthaIamic acid methyl ester;
3,5-difluoro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]--benzamide;
4-chloro-3-fluoro-N-[cis-4-(quinolin-2-y]amino)-cyclohexyI]-benzamide;
C-[(4-chloro-phenyl)-ethyl-amino]-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide;
6-chloro-N-[cis-4-(4-methyI-quinoIin-2-y]amino)-cyc]ohexyl]-nicotinamide;
3-chloro-5-fluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3,4,5-trifluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
5-bromo-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyC1-5hexyl]-nicotinamide;
4-methyl-N-{cis-4-[(4-methylquinolin-2-yl)amino]cyC1-5hexyl}benzamide;
2-(4-chlorophenoxy)-N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}-acetamide;
3,4,5-trimethoxy-N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}benzamide;
2-(3,4-difluorophenyI)-N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}-acetamide;
2-(2-bromo-4,5-dimethoxyphenyl)-N-{cis-4-[(4-methylquinolin-2-yI)amino]-cyclohexyl}-
acetamide;
2,6-dimethoxy-N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}nicotinamide;
N-{cis-4-[(4-methylquinoiin-2-yl)amino]cyclohexyl}-4-(trifluoromethoxy)-benzamide;
5-chloro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide; and
5-fluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Ri is selected from the group consisting of:
C1-16 alkyl, and
C1-16 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••Cw aikyl,

97
••C1-5 alkyl substituted by halogen,
••C1-5 alkoxy, and
••C1-5 alkoxy substituted by halogen,
L is Formula (XV);
Y is -C(O)NR5-;
wherein carbocyclic aryl is phenyl; and
halogen is fluoro, chloro, or bromo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Rj is selected from the group consisting of:
C1-16 alkyl, and
C1-16 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
"C1-5 alkyl, and
"C1-5 alky! substituted by halogen,
wherein carbocyclic aryl is phenyl; and
halogen is fluoro, chloro, or bromo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R2 is methyl; p is 0; R3 and R4 are both
hydrogen; A and B are both single bonds; and R5 is hydrogen: or a pharmaceutically acceptable salt,
hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
cis-N-[(lR)-l-(4-bromophenyl)ethyl]-4-[(4-methylquinolin-2-yl)amino]-
cyclohexanecarboxamide;

98
cis-N- {(1S)-1 -[3,5-bis(trifluoromethyl)phenyl]ethyI} -4-[(4-methylquinolin-2-y I)amino]-
cyc lohexanecarboxam ide;
cis-N-[(lR)-I-(2-fluorophenyl)ethyl]-4-[(4-methylquinoIin-2-y!)amino]-
cyclohexanecarboxamide;
cis-N-[(lS)-l-(2-fluorophenyI)ethyl]-4-[(4-methylquinoIin-2-yl)amino]-
cyclohexanecarboxamide;
cis-4-[(4-methylquinolin-2-yl)amino]-N-{(lS)-l-[2-(trifluoromethyl)phenyl]ethyl}-
cyc lohexanecarboxam ide;
cis-4-[(4-methylquinolin-2-yl)amino]-N-{(lS)-l-[3-(trifluoromethyl)phenyl]ethyl}-
cyc lohexanec arboxam ide;
cis-N-[(lR)-l-(4-chlorophenyl)ethyI]-4-[(4-methylquinolin-2-yl)amino]-
cyclohexanecarboxamide; and
cis-N-[(lS)-l-(4-chlorophenyl)ethyl]-4-[(4-methylquinolin-2-yl)amino]-
cyc lohexanecarboxam ide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
cis-N-[(lR)-l-(4-bromophenyl)ethyl]-4-[(4-methylquinolin-2-yl)amino]-
cyclohexanecarboxamide;
cis-N-[(IS)-l-(2-fluorophenyl)ethyl]-4-[(4-methylquinolin-2-yi)ammo]-
cyclohexanecarboxamide;
cis-4-[(4-methylquinolin-2-yl)amino]-N-{(lS)-l-[2-(trifluoromethyl)phenyl]ethyI}-
cyclohexanecarboxamide; and
cis-4-[(4-methyIquinolin-2-yl)amino]-N-{(lS)-l-[3-(trifluoromethyl)phenyl]ethyl}-
cyclohexanecarboxamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Ri is selected from the group consisting of:
(i) C1-5 alkyl, and

99
C1-5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•C1-5 alkoxycarbonyl,
•C1-5 alkylthio,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
"C1-5 alkyl, and
••C2.3 alkenyl,
(ii) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by carbocyclic aryl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•cyano,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxycarbonyl,
•C1-5 alkoxy.,
•C1-5 alkoxy substituted by carbocyclic aryl,
•C3-6 cycloatkoxy,
'carbocyclic aryloxy,
•C1-5 alkylthio, and
•carbocyclic aryl,
(iv) heterocyclyl, and

100
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alky 1,
•C1-5 alkyl substituted by halogen, and
•carbocyclic aryl;
L is Formula (VII);
Y is -C(O)NR5-;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is 2,3-dihydro-benzo[l,4]dioxinyl,
3,4-dihydro-2/7-benzo[b][l,4]-dioxepinyl, benzo[l,3jdioxolyl, fury], or isoxazolyl;
and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutical ly acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R2 is hydrogen, methyl, methylamino, or
dimethylamino; p is 0; R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-; R5 is
hydrogen; or a pharmaceutical ly acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•C1-5 alkoxycarbonyl,
•carbocyclic aryl, and
•carbocyclic aryl substituted by halogen,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,

101
•C1-5 alky],
•C1-5 alkyl substituted by halogen, and
•C1-5 alkoxy,
(iii) heterocyclyl,
heterocyclyl substituted by C1-5 alkyl, and
heterocyclyl substituted by carbocyclic aryl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is isoxazolyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
N-(2-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-N'-(2-ethyl-6-
methylphenyl)urea;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-mesitylurea;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-(2,4,6-trichlorophenyl)-
urea;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-(2,4,6-tribromophenyl)-
urea;
N-(2,4-dibromo-6-fluorophenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)urea;
N-(2,6-diethylphenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)urea;
N-(2-chlorobenzyl)-N'-(cis-4-{[4-^dimethylamino)quinolin-2-yl]amino}-cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-(2-ethyl-6-
isopropylphenyl)urea;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-(2-isopropyl~6-
methylphenyl)urea;

102
N-(2-tert-butyl-6-methylphenyl)-N'-(cis-4-{[4-(dimethyiamino)quinolin-2-yi]amino}-
cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-N'-(diphenyImethyl)urea;
N-(4-bromo-2,6-dimethylphenyI)-Nt-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyc!ohexyl)urea;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-(3-methyl-5-
phenylisoxazol-4-yl)urea;
N-(cis-4- {[4-(dimethylamino)quinolin-2-y l]amino}cyclohexyl)-N'-1 -naphthylurea;
N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexyl)-N'-[ 1 -(1 -naphthyl)ethy 1]-
urea;
methyl N-{[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyi)-arnino]carbonyl}-
phenylalaninate;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-(3,4,5-
trimethoxyphenyl)urea;
N-(5-chloro-2,4-dimethoxyphenyl)-N'-(cis-4- {[4-(dimethylamino)quinolin-2-y l]amino} -
cyclohexyl)urea;
N-(4-bromo-2-methylphenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)urea;
N-[(cis-4-{[4-(dimethyIamino)q«inolin~2-yl]amino}cyclohexyl)methyl]-Nl-(2-ethyl-6-
methylphenyl)urea;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyI]-N'-mesitylurea;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-N'-(2,4,6-
trichlorophenyl)urea;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)methyI]-N'-(2,4,6-
tribromoph eny l)urea;
N-(2,4-dibromo-6-fluorophenyI)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}-
cyclohexyl)methyi]urea;
N-(2,6-diethylphenyl)-Nt-[(cis^-{[4-(dimethylamino)quinoIin-2-yl]amino}-cyclohexyl)-

103
methyl] urea;
N-[2-chloro-6-(trifluoromethyl)phenyI]-N'-[(cis-4-{[4-(dimethylamino)-quinolin-2-yl]-
amino}cyclohexyl)methyl]urea;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyi)methy]]-N'-(2-ethyI-6-
isopropylphenyi)urea;
N-[(cis-4-{[4-(dimethy!amino)quinolin-2-yI]amino}cyclohexyl)methyl]-N'-(2-isopropyl-6-
methylphenyl)urea;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)methyl]-N'-(2-methyl-3-
nitrophenyl)urea;
N-(2-tert-butyl-6-methylphenyl)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}-
cyclohexyl)methyl]urea;
N-(2-tert-butylphenyl)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]-amino}cyclohexyl)-
methyljurea;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-N'-
(diphenylmethyl)urea;
N-(4-bromo-2,6-dimethylphenyI)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
eye lohexyl)methyl] urea;
N-(2,3-dichlorophenyl)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]-amino}cyclohexyl)-
methyl] urea;
N-(2?6-diisopropylphenyl)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]-amino}-
cyclohexyl)methyl]urea;
l-(2,3-dichloro-phenyl)-3-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-urea; and
l-(2,3-dichloro-phenyl)-3-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexylmethyl]-urea;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R] is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the group
consisting of:

104
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
"C1-5 alkoxy,
(ii) carbocyclyl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•cyano,
•nitro,
•C,_s alkyl,
•C1-5 alkyl substituted by halogen,
•C[-5 alkoxy carbonyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by halogen,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino, and
•carbocyclic aryl,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alky!,
•C1-5 alkoxy carbonyl, and
'carbocyclic aryl;
L is Formula (VII);
Y is -C(S)NR5-;

105
wherein carbocyclic aryl is phenyl or naphthyl;
carbocyclyl is bicyclo[2.2.1]heptyl;
heterocyclyl is 2,3-dihydro-benzo[l,4]dioxinyl, benzo[l,3]dioxolyl,
isoxazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-; R5 is hydrogen; or a
pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Ri is selected from the group consisting of:
(i) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C,.s alkyl,
•C[.5 alky I substituted by halogen,
•Ci-g alkoxy,
•mono-Cj.5 alkylamino, and
*di-C1-5 alkylamino,
(ii) heterocyclyl, and
heterocyciyl substituted by C1-5 alkyl, and
heterocycly! substituted by C1-5 alkoxy carbonyl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyciyl is thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:

106
N-(2,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-yl]-amino}cyclohexyl)-
thiourea;
N-(cis-4-{[4-(dimethylamino)quino!in-2-yl]amino}cyclohexyl)-N'-(3,4,5-
trimethoxyphenyl)thiourea;
N-[4-(dimethyIamino)-l-naphthyl]-N'-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cy c lohexy l)th iourea;
N-(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}cyclohexyI)-N'-(2,4,6-tribromophenyI)-
thiourea;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-(2,4,6-trichlorophenyl)-
thiourea;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-mesitylthiourea;
N-(2J6-diethy!pheny])-N'-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)-
thiourea;
N-(4-bromo-2,6-dimethyIphenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
eye lohexy l)thiourea;
N-(4-bromo-2-methyIphenyl)-N'-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}-
eye lohexy l)thiourea;
N-[4-bromo-2-(trifluoromethy!)phenyl]-N'-(cis-4-{[4-(dimethylamino)-quinolin-2-yl]-
amino}cyclohexyl)thiourea;
N-(5-chIoro-2,4-dimethoxyphenyI)-Nt-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}-
cyclohexyl)thiourea;
N-(2,4-dibromo-6-fluorophenyl)-NI-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)thiourea;
N-(2,4-dichloro-6-methyIphenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-yJ]amino}-
cyclohexyl)th iourea; and
methyl 3-({[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-amino]-
carbonothioyl}amino)-4-methylthiophene-2-carboxylate;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.

107
In some embodiments of the present invention, K] is selected from the group consisting of:
(i) C|_g alkyl, and
C|_8 alkyi substituted by substituent(s) independently selected from the group
consisting of:
•halogen,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
••nitro, and
••C1-5 alkoxy,
(ii) C2-5 alkenyl,
(iii) carbocyclyl,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•Cj.5 alkyl,
•C1-5 alkyl substituted by halogen, and
•C|_5 alkoxy;
L is Formula (VII);
Y is -C(O)O-;
wherein carbocyclic aryl is phenyl or naphthyl;
carbocyclyl is 9//-fluorenyl or menthyl; and
halogen is fluoro, chloro, bromo, or iodo;

108
or a pharmaceutical ly acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-; or a pharmaceuticaliy
acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Q is Formula (III);
(i) C]_8 alkyl, and
Ci_g alkyl substituted by substituent(s) independently selected from the group
consisting of:
•halogen,
"OXO,
•C1-5 alkoxy,
*C1-5 alkoxy substituted by carbocyclic aryl,
•C1-5 alkylcarbonyloxy,
•carbocydic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by nitro,
•heterocyclyloxy,
•heterocyclyloxy substituted by C1-5 alkyl,
*Ct_5 alkoxycarbonyl,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C]-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•mono-C1-5 alkylamino substituted by carbocyclic aryl,
•di-C]., alkylamino,
•di-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino substituted by carbocyclic aryl,
•mono-carbocyclic arylamino,

109
•mono-carbocyclic arylamino substituted by C1-5 alky I,
di-carbocyclic arylamino,
•di-carbocyclic arylamino substituted by C1-5 alkyl,
•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted C1-5 alkyl,
•Cj.g alkylthio,
•C1-5 alkylthio substituted by substituent(s) independently selected from the
group consisting of:
••carbocyclic aryl,
••carbocyclic aryl substituted by halogen, and
"carbocyclic aryl substituted by C1-5 alkoxy,
•carbocyclic arylthio,
•heterocyclytthio,
•heterocyclylthio substituted by C1-5 alkyl,
•C3-6 cycloalkyl,
•C3-6 cycloalkenyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C1-5 alky],
••C1-5 alkoxy,
••C2-5 alkenyl, and
"C2-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
••"carbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulfmyl,
•carbocyclic aryl,

110
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••nitro,
C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
•••oxo,
"••carbocyclic aryl, and
•••heterocyclyl,
"C2-5 alkenyl,
•*C^5 alkoxy,
••C1-5 alkoxy substituted by halogen,
••C1-5 alkoxy substituted by carbocyclic aryl,
'•carbocyclic aryloxy,
••mono-carbocyclicarylaminocarbonyl,
••mono-carbocyclic arylaminocarbonyl substituted by halogen,
•• di-carbocyclic arylaminocarbonyl,
••di-carbocyclic arylaminocarbonyl substituted by halogen,
•'carbocyclic aryl, and
"heterocyclyl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5 alkyl,
"C1-5 alkoxy,
••C1-5 alkoxy substituted by carbocyclic aryl,

Ill
"carbocyclic aryl, and
••carbocyclic aryl substituted by halogen,
(ii) C2.7 alkenyl, and
C2,7 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
"C1-5 alkoxy,
(iii) C2-5 alkynyl,
(iv) C3-i2 cycloalkyl, and
C3-12 cycloalkyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkyl,
•C1-5 alkyl substituted by oxo,
•C1-5 alkyl substituted by carbocyclic aryl, and
•carbocyclic aryl,
(v) carbocyclyl,
(vi) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
•C1-50 alkyl,

112
•C1-5O alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
**oxo,
••carbocyclic aryloxy,
••carbocyclic aryl, and
••carbocyclic aryl substituted by Cj.5 alkyl,
•C]_7 alkoxy,
•C1.7 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
'•carbocyclic aryl, and
"halogenated carbocyclic aryl,
•C2-5 alkenyloxy,
•C3-6 cycloalkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by nitro,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•carboxy,
•C1-5 alkoxycarbonyl,
•moao-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C}-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•amino,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,

113
•di-C1-5 aikylamino substituted by cyano,
•C2-5 alkynylcarbonylamino,
•C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,
■C1-5 alkoxycarbonylamino,
•(carbocyciic aryl)NHC(O)NH,
•(carbocyclic aryI)NHC(O)NH substituted by C\.$ alkoxy,
"(carbocyclic aryl)NHC(O)NH substituted by haloganated C1-5 aikoxy,
•carbocyclic aryl azo,
•carbocyclic aryl azo substituted by mono-C1-5 alkyiamino,
•carbocyclic aryl azo substituted by di-Cj_5 aikylamino,
•C1-5alkylthio,
•C3.5 alkylthio substituted by halogen,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by nitro,
•carbocyclic arylthio substituted by cyano,
•aminosulfonyl,
•mono-C1-5 alkylaminosulfonyl,
•di-Cj.5 alkylaminosulfonyl,
•heterocyclylsulfonyl,
•C3-6 cyeloalkyi,
•C3-6 cyeloalkyi substituted by C1-5 alkyl,
•carbocyclic aryl,
•heterocydyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
»C1-5 alkyl,
••carbocyclic aryl, and
••halogenated carbocyclic aryl,

114
(vii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
"C1-5 alkyt substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••hydroxy,
••C1-5 alkylthio,
•"C1-5 alkylthio substituted by carbocyclic aryl,
"C1-5 alkylthio substituted by halogenated carbocyclic aryl,
"carbocyclic aryl,
••carbocyclic aryl substituted by halogen, and
"heterocyclyl,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by Cj.5 alkyl,
•C1-5 alkylthio,
•C2-5 alkenylthio,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by C1-5 alkoxycarbonyl,
•C1-5 alkylsulfonyt,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by C1-5 alkyl,
•C1-5 alkoxycarbonyl,
•C1-5 alkoxycarbonyl substituted by carbocyclic aryl,

115
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,
"C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
"heterocyclyl;
wherein carbocyclic aryl is phenyl, naphthyl, or anthranyl;
carbocyclyl is 1,2,3,4-tetrahydronaphthyl, 1-oxo-indanyl, 9-fluorenyl,
9//-fluorenyl, 9-oxo-9//-fluorenyl, adamantly, bicyclo[2.2.1]heptenyl,
bicyclo[2.2.1]heptyl, indanyl, indenyl, ormenthyl;
heterocyclyl is 1,2,3-triazolyl, lif-indolyl, l//-pyrrolyl,
2,3-dihydro-l-oxo-isoindolyl, 2,3-dihydro-benzo[l,4]dioxinyl,
2,4-dihydro-3-oxo-pyrazolyl, 2//-benzopyranyl, 2-oxo-benzopyranyl,
3,4-dihydro-2#-benzo[b][l,4]dioxepinyl, 4,5,6,7-tetrahydro-benzo[b]thienyl,
4//-benzo[ 1,3]dioxinyl, 4-oxo-1,5,6,7-tetrahydro-indolyl, 4-oxo-benzopyranyl,
9//-carbazolyI, 9//-xanthenyl, azetidinyl, benzo[l,3]dioxolyl,
benzo[2,l,3]oxadiazolyl5benzo[l,2,5]oxadiazolyl, benzo[2,l,3]thiadiazolyl,
benzo[b]thienyl, benzofuryl, benzothiazolyl, furyl, imidazo[2,l-b]thiazolyl,
isoxazolyl, morpholino, morpholinyl, oxazolyl, phenanthro[9,10-d]oxazolyl,
piperidyl, pyrazolyl, pyridyl, pyrimidyl, quinolyl, quinoxalyl, tetrahydrofuryl,
thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R] is selected from the group consisting of:
(i) Ct_7 alkyl, and
C1.7 alkyl substituted by substituent(s) independently selected from the group

116
consisting of:
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic ary],
•carbocyciic aryloxy,
•mono-C1-5 alkylamino,
•mono-Ci0- alkylamino substituted by substituent(s) independently selected
from the group consisting of:
••cyano, and
••carbocyclic aryl,
•di-Ci-s alkylamino,
•di-C1-5 alkylamino substituted by substituent(s) independently selected from
the group consisting of:
••cyano, and
••carbocyclic aryl,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by C1-5 alkyl,
•di-carbocyclic arylamino substituted by C\.5 alkyl,
•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted by C1-5 alkyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,
»C1-5 alky],
"C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:

117
•"oxo, and
•••carbocyclic aryl,
••C1-5 alkoxy,
•heterocyclyl, and
•heterocyclyl substituted by carbocyclic aryl,
(ii) C2-7 alkenyl, and
C2.7 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by C1-5 alkoxy,
(iii) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkyl, and
•Cj_5 alkyl substituted by carbocyclic aryl,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•cyano,
*C1-5 alkyl,
•C1-5 atkyl substituted by halogen,
*C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••carbocyclic aryl,

118
••carbocyclic aryl substituted by halogen,
•C2-5 alkenyloxy,
*mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
"di-C|.5 alkylamino substituted by cyano,
•C1-5 alkylthio, and
•C1-5 alkylthio substituted by halogen,
(v) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alky],
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••hydroxy, and
••carbocyclic aryl,
•C1-5 alkoxy,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by Ct-5 alkoxycarbonyl,
•C1-5 alkoxycarbonyl,
•carbocyclic aryl,
'carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
"C1-5 alkyl substituted by halogen;
L is Formula (VII);

119
Y is a single bond or -CH2-;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is li-Mndolyl, li/-pyrroryl, 2,3-dihydro-benzo[l,4]dioxinyl,
4-oxo-benzopyranyl, 9-tf-carbazoIyl, azetidinyl, benzo[1.3]dioxolyl, benzo[b]thienyl,
furyl, imidazo[2,l-b]thiazolyl, pyrazolyl, pyridyl, orthienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R? is methylamino or dimethyl am in o; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-; or a pharmaceutically
acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•mono-Cj-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino,
•di-C1-5 alkylamino substituted by cyano,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by C^ alkyl,
•di-carbocyclic arylamino substituted by d_5 alkyl,
•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted by C1-5 alkyl,
•carbocyclic aryl, and
•carbocyclic aryl substituted by C1-5 alkoxy,
(ii) C2-5 alkenyl, and
C7.5 alkenyl substituted by carbocyclic aryl,

120
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•C1-5 alkyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by halogen,
•mono-C1-5 alkylamino, and
•di-C1-5 alkylamino,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
-C1-5 alkyl,
•C1-5 alkyl substituted by carbocyclic aryl,
•C1-5 alkoxy,
•C1-5 alkoxycarbonyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
"C1-5 alkyl, and
**C1-5 alkyl substituted by halogen;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is l/f-indolyl, 4-oxo-benzopyranyl, azetidinyl,
benzo[l,3]dioxolyl, or pyrazolyl; and
halogen is fluoro, chloro, bromo, or iodo;

121
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R] is selected from the group consisting of:
(i) C3.5 alky], and
C1-5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•mono-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino,
•di-C1-5 alkylamino substituted by cyano,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted by C1-5 alkyl, and
•carbocyclic aryl,
(ii) C2_5 alkenyl, and
C2-5 alkenyl substituted by carbocyclic aryi,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
"halogen,
•hydroxy,
•C1-5 alkoxy, and
•C1-5 alkoxy substituted by halogen,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkyl,

122
•C1-5 alkyl substituted by carbocyclic aryl,
•C1-5 alkoxy,
•C1-5 alkoxycarbonyi,
•carbocyclic aryl, and
•carbocyclic aryl substituted by halogen;
wherein carbocyclic aryl is phenyl;
heterocyclyl is l//-indolyl, azetidinyl, or pyrazolyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
N2-{cis-4-[(2,6-dimethoxybenzyl)amino]cyclohexyI}-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-{cis-4-[(2-ethoxybenzyI)amino]cyclohexyl}-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-{cis-4-[(lH-indol-3-ylmethyl)amino]cyclohexyl}-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-{cis-4-[(2,5-dimethoxybenzyl)amino]cyclohexyl}-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(4-methoxy-l-naphthyl)methyl]amino}cyclohexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(5-methoxy-lH-indoI-3-yl)methyl]amino}cyclohexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
4-bromo-2-{[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroqumazolin-2-yl]amino}-
cyclohexyl)amino]methyl}-6-methoxyphenol;
N2-(cis-4-{[(5-bromo-lH-indol-3-yl)methyl]amino}cyC1-5hexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroqu i nazol i ne-2,4-d iamine;
4-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-

123
amino]methyI}-2,6-dimethoxyphenol;
N2-{cis-4-[(3-ethoxy-4-methoxybenzyl)amino]cyclohexyl}-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoIine-2,4-diamine;
N4,N4-dimethyl-N2-{cis-4-[({344-(trifluoromethyl)phenyl]4H-pyrazo]-4-yl}methyI)-
amino]cyclohexyl}-5,6,7,8-tetrahydroquina2oline-2,4-diamine;
N4,N4-dimethyI-N2-{cis-4-[(3,4,5-trimethoxybenzyl)amino]cyclohexyI}-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethyl-N2-{cis-4-[(pentamethylbenzyI)amino]cyclohexyi}-5,6,7,8-
tetrahydroquinazoIine-2,4-diamine;
N2-{cis-4-[(3,5-dimethoxybenzyl)amino]cyC1-5hexyl}-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
4-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyI)-
amino]methyl}-2-iodo-6-methoxyphenol;
4-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yi]amino}-cyclohexyI)-
amino]methyl}-2,6-dimethyIphenol;
3-{[(cis-4-{[4-(diraethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyl)-
araino]methyl}-6,8-dimethyI-4H-chromen-4-one;
ethyl 4,6-dichioro-3-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino}cyclohexyl)amino]methyl}-lH-indole-2-carboxyIate;
N2-[cis-4-({[3-(4-fluorophenyl)-lH-pyrazol-4-yl]methyl}amino)cyC1-5hexyl]-N4,N4-
dimethyI-5,6,7,8-tetrahydroquinazoIine-2,4-diamine;
N4,N4-dimethyl-N2-[4-(pentamethylphenylmethyl-amino)-cyclohexyl]-5,6,7,8-tetrahydro-
quinazoi ine-2,4-diam ine;
3-[{2-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}cyC1-5hexyI)-
amino]ethyl}(3-methylphenyl)amino]propanenitrile;
3-[{2-[(cis-4-{[4-(dimethylamino)-5J6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)-
amino]ethyl}(phenyl)amino]propanenitrile;
N-{(lS)-I-benzyl-2-[(cis-4-{[4-(dimethylamino)-5,6r7,8-tetrahydroquinazolin-2-yl]amino}-

124
cyC1-5hexyl)amino]ethyi}-4-methyIbenzenesuIfonamide;
N2-(cis-4-{[2-(3,5-dimethoxyphenyl)ethyl]amino}cyclohexyl)-N4,N4-dimethyI-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-[cis-4-({[l-(diphenyImethyl)azetidin-3-yI]methyl}amino)cyclohexyl]-N4,N4-dimethyI-
5,6,7,8-tetrahydroq u inazol ine-2,4-d iam ine;
N2-(cis-4-{[(2,6-dimethoxybenzyl)amino]methyl}cyC1-5hexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(2-ethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-dimethyl-5?6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(lH-indol-3-ylmethyl)amino]methyl}cyclohexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(2,5-dimethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-[cis-4-({[(4-methoxy-l-naphthyl)methyl]amino}methyl)cyclohexyI]-N4,N4-dimethyl-
5,6,7,8-tetrahydroquinazoiine-2,4-diamine;
N2-[cis-4-({[(5-methoxy-lH-indol-3-yl)methyl]amino}methyl)cyclohexyl]-N4,N4-dimethyl-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
4-bromo-2-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)methyl]amino}methyI)-6-methoxyphenoI;
N2-[cis-4-( {[(5-bromo-l H-indoI-3-yl)methyI]amino} methy l)cyclohexyI]-N4,N4-dimethy 1-
5,6,7,8-tetrahydroquinazoIine-2,4-diamine;
N2-(cis-4-{[(3-ethoxy-4-methoxybenzyI)amino]methyl}cyclohexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethyI-N2-(cis-4-{[({3-[4-(trifluoromethyI)phenyl]-lH-pyrazol-4-yl}methyl)-
amino]methyl}cyclohexyl)-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(3,4,5-trimethoxybenzyl)amino]-methyI}cyclohexyl)-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N"-{cis-4-{[(3,5-dimethoxybenzyI)amino]methyl}cyclohexyl)-N4,N -dimethyl-5,6,7,8-

125
tetrahydroquinazoline-2,4-diamine;
4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)-
methyl]amino}methyI)-2-iodo-6-methoxyphenol;
4-({[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyI)-
methyl]amino}methyl)-2,6-dimethyIphenoI;
3-chloro-4-({[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]aniino}-
cyclohexyl)methyl]amino}methyl)phenol;
N2-[cis-4-({[4-(diethylamino)benzyl]amino}methyl)cyclohexyl]-N4,N4-dimethyI-5,6,7,8-
tetrahydroq u inazo 1 ine-2,4-d iam ine;
N2-(cis-4-{[(3,3-diphenylprop-2-en-l'yl)amino]methyl}cyclohexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
4-({[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2'yI]amino}cyclohexyI)-
methyl]amino}methyl)-2-ethoxyphenoI;
N2-{cis-4-[({[4-(dimethy!amino)-l-naphthyl]methyl}amino)methyl]-cyclohexyl}-N4,N4-
dimethy]-5,6,7,8-tetrahydroquinazoIine-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,6-trimethoxybenzyl)amino]methyl}-cyclohexyl)-5,6,7,8-
tetrahydroqu inazo line-2,4-diam ine;
2-bromo-4-chloro-6-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino}cyclohexyl)methyl]amino}methyl)phenol;
N2-(cis-4-{[(2,5-diethoxybenzyI)amino]methyl}cyclohexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(2,4-diethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(3,5-dibromo-2-methoxybenzyI)amino]methyl}cyclohexyI)-N ,N -dimethyl-
5,6,7;8-tetrahydroquinazoIine-2?4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-triethoxybenzyl)amino]methyl}-cyclohexyl)-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-trimethoxybenzyl)amino]methyI}-cyclohexyl)-5,6,7,8-

126
tetrahydroquinazoIine-2,4-diamine;
^-[cis^-d^T-methoxy-lp-benzodioxoi-S-y^methyljaminolmethylJ-cyC1-5hexylJ-N4^4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)-
methyl]amino}methyl)-2-methylphenoi;
N2-(cis-4-{[(4-methoxy-2,5-dimethylbenzyI)amino]methyl}cyclohexyl)-N4,N4-dimethyl-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
4-({[(cis-4-{[4-(dimethylamino)-556,7,8-tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)-
methyl]amino}methyl)-2-fluoro-6-methoxyphenol;
N4,N4-dimethyI-N2-[cis-4-( {[(1 -phenyl-5-propyl-1 H-pyrazol-4-yl)methy l]amino}methyl)-
cyclohexyl]-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N2- {cis-4-[{ {[ 1 -(4-chlorophenyI)-5-propyl-l H-pyrazol-4-y I] methyl j -amino)methy 1]-
cyclohexyl}-N4,N4-dimethyl-5,6,7,8-tetrahydroquina2oline-2,4-diamine;
N2-{cis-4-[2-(4-bromo-2-trifluoromethoxy-phenyI)-ethylarnino]-cyclobexyl}-N4,N4-
dimethyI-5,6,7,84etrahydro-quinazoline-2,4-diamine;
N2-{cis-4-[2-(4-bromo-2-trifluoromethoxy-phenyl)-ethylamino]-cyclohexyl}-N4-methyl-
5,6,7,8-tetrahydro-quinazoline-2,4-diamine;
N2-{cis-4-[(4-bromo-2-trifluoromethoxy-benzyl)amino-methyl]-cyclohexyl}-N4-methyI-
S^^^-tetrahydro-quinazoline^^-diamine;
N2-{cis-4-[(4-bromo-2-trifluoromethoxy-benzyl)amino-methyl]-cyclohexyI}-N4,N4-
dimethyl-5,6,7,8-tetrahydro-quinazoiine-2,4-diamine;
N4,N4-dimethyI-N2-{cis-4-[(24rifluoromethoxy-benzyI)amino-methyl]-cyclohexyl}-5,6,7,8-
tetrahydro-quinazoline-2,4-diamine; and
N4-methyl-N2-{cis-4-[(2-trifluoromethoxy-benzyl)amino-methyl]-cyclohexyl}-5,6,7,8-
tetrahydro-quinazoline-2,4-diamine;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:

127
N2-(cis-4-{[(5-methoxy-3H-indol-3-yi)methyl]amino}cyclohexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
ethyl 4,6-dichloro-3-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquin azoIin-2-yl]-
amino}cyclohexyl)ammo]methyl}-lH-indole-2-carboxylate;
N2-[cis-4-({[3-(4-fIuorophenyl)-lH-pyrazoI-4-yl]methyl}amino)cyclohexyI]-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoIine-2,4-diamine;
3-[{2-[(cis-4-{[4-(dtmethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}cyC1-5hexyI)-
amino]ethyl}(phenyl)amino]propanenitrile;
N-{(lS)-l-benzyl-2-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cydohexyl)amino]ethyl}-4-methylbenzenesulfonamide;
N2-[cis-4-( {[ 1 -(diphenylmethyI)azetidin-3-yl]methyl} amino)cyclohexyl]-N4,N4-dimethyI-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(2,6-dimethoxybenzyl)amino]methyl}cyclohexyI)-N4,N -dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-[cis-4-({[(5-methoxy-lH-indol-3-yl)methyl]amino}methyl)cyclohexyl]-N4,N -dimethyl-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N2-[cis-4-({[(5-bromo-lH-indoI-3-yl)methyl]amino}methyl)cyC1-5hexyl]-N4,N4-dimethyI-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(3-ethoxy-4-methoxybenzyl)amino]methyl}cyclohexyI)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}cyclohexyl)-
methyl]amino}methyl)-2-iodo-6-methoxyphenol;
N2-(cis-4-{[(3,3-diphenylprop-2-en-l-yI)amino]methyl}cyclohexy])-N4,N4-dimethyI-5,6,7,8-
tetrahydroquinazoIine-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,6-trimethoxybenzyl)amino]methyl}-cyclohexyl)-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[{2,5-diethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;

128
N2-(cis-4-{[(2,4-diethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(3!5-dibromo-2-methoxybenzyI)amino]methyl}cyc]ohexy])-N4,N4-dimethyI-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-triethoxybenzyl)amino]methyl}-cyclohexyl)-5,6,7,8-
tetrahydroquinazoiine-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-trimethoxybenzyl)amino]methyl}-cyclohexyl)-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethyl-N2-[cis-4-( {[(1 -phenyI-5-propyI-1 H-pyrazol-4-yl)methyl]amino} methyl)-
cyclohexyI]-5,6,7,8-tetrahydroquinazoIine-2,4-diamine;
N2-{cis-4-[({[l-(4-chlorophenyI)-5-propyl-lH-pyrazol-4-yl]methyl}-amino)methyl]-
cyclohexyI}-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamme;
N2-{cis-4-[2-(4-bromo-2-trifluoromethoxy-phenyl)-ethylamino]-cyC1-5hexyl}-N4,N4-
dimethyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine;
N"-{cis-4-[(4-bromo-2-trifluoromethoxy-benzyl)amino-methyI]-cyC1-5hexyl}-N -methyl-
5,6,7,8-tetrahydro-quinazoline-2,4-diamine;
N2-{cis-4-[(4-bromo-2-trifluoromethoxy-benzyI)amino-methyl]-cyclohexyl}-N4,N4-
dimethyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine; and
N4,N4-dimethyl-N2-{cis-4-[(2-trifluoromethoxy-benzyl)amino-methyl]-cyclohexyl}-5,6,7,8-
tetrahydro-quinazoline-2,4-diamine;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R; is selected from the group consisting of:
(i) C1-5 alky], and
Q.5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,

129
•C1-5 alkylcarbonyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by nitro,
•heterocyclyloxy,
•heterocyclyloxy substituted by C1-5 alkyl,
•mono-C1-5 alkyl am inocarbonyl,
*di-C1-5 alkylaminocarbonyl,
•carbocyclic arylcarbonylamino,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl, and
••carbocyclic aryl substituted by substituent(s) independently
selected from the group consisting of:
•••halogen, and
•C1-5 alkoxy,
•carbocyclic arylthio,
•heterocyclylthio,
•heterocyclylthio substituted by C1-5 alky],
•C3-6 cycloalkyl,
•C3^ cycloalkenyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C1-5 alkyl,
••C1-5 alkoxy,

130
"C2-s alkenyl, and
•*C2o alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and
•••carbocyclic aryl substituted by Cj.5 alkylsulflnyl,
•carbocyclic ary],
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••nitro,
••C,-5 alkyl,
"C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
•••oxo,
•••carbocyclic aryl, and
"•heterocyclyl,
••C1-5 alkoxy,
"C1-5 alkoxy substituted by halogen,
••C1-5 alkoxy substituted by carbocyclic ary!,
••carbocyclic aryloxy,
••mono-carbocyclicarylaminocarbonyl,
••mono-carbocyclic arylaminocarbonyl substituted by halogen,
••di-carbocyclic arylaminocarbonyl,
••di-carbocyclic arylaminocarbonyl substituted by halogen,
"carbocyclic aryl, and
"heterocyclyl,
"heterocyclyl, and

131
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5 alky I,
••C1-5 alkoxy,
*"C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryl, and
••carbocyclic aryl substituted by halogen,
(ii) C2,5 alkenyl, and
C2-5 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen, and
••nitro,
(iii) C3-6 cycloalkyl, and
C3-6 cycloalkyt substituted by substituent(s) independently selected from the
group consisting of:
•Ci_s alky!,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
*"oxo, and
••carbocyclic aryl,
•carbocyclic aryl,
(iv) carbocyclyl,
(v) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:

132
•halogen,
•hydroxy,
•cyano,
•nirro,
•d.salkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••oxo,
••carbocyclic aryloxy,
••carbocyclic aryl, and
••carbocyclic aryl substituted by d-5 alkyl,
•Cj-5 alkoxy,
*C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
•*carbocyciic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by d-5 alkoxy,
•mono-d-5 alkylaminocarbonyl.,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
*di-C]-5 aikylaminocarbonyl substituted by carbocyclic aryl,
•amino,
•mono-d-5 alkylamino,
•di-Ci-s alkylamino,
•C2-5 alkynylcarbonylamino,
"C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,

133
•(carbocyclic aryl)NHC(O)NH,
•(carbocyciic aryl)NHC(O)NH substituted by C1-5 alkoxy,
•(carbocyclic aryI)NHC(O)NH substituted by haloganated C1-5 alkoxy,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by halogen,
•carbocyciic arylthio,
•carbocyclic arylthio substituted by cyano,
•mono-C]_g alky lam inosulfonyl,
•di-C1-5 alkylaminosulfonyl,
•carbocyclic aryl,
•heterocycly],
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
-Csalkyl,
"carbocyclic aryl, and
••halogenated carbocyclic aryl,
(vi) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
"halogen,
•nitro,
•Chalky],
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
"halogen,
••C1-5 alkylthio,
••C1-5 alkylthio substituted by carbocyclic aryl,
••C1-5 alkylthio substituted by halogenated carbocyclic aryl,

134
••carbocyclic aryl,
••carbocyclic aryl substituted by halogen, and
••heterocyclyl,
•C1-5alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkyi,
•C1-5 alkylthio,
•C2.5 alkenylthio,
'carbocyclic arylthio,
•C1-5 alkylsulfonyl,
'carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by C1-5 alkyi,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
••C,_5 alkyi,
•heterocyclyl;
L is Formula (VII);
Y is -C(O)-;
wherein carbocyclic aryl is phenyl, naphthyl, or anthranyl;
carbocyclyl is 1,2,3,4-tetrahydronaphthyl, l-oxo-indanyl,
9-oxo-9//-fluorenyI, or indenyl;
heterocyclyl is 1,2,3-triazolyI, 1 //-indolyl, l//-pyrrolyl,
2,3-dihydro-l-oxo-isoindoIyl, 2,4-dihydro-3-oxo-pyrazolyl, 2#-benzopyranyl,
2-oxo-benzopyranyI, 4-oxo-1,5,6,7-tetrahydro-indolyl, 9//-xantheny 1,
benzo[l,3]dioxolyl, benzo[2,l,3]oxadiazolyl, benzo[l,2;5]oxadiazolyl,

135
benzo[b]thienyl, benzofuryl, benzothiazolyl, furyl, isoxazolyl, morpholino, pyrazolyl,
pyridyl, pyrimidyl, quinolyl, quinoxalyl, thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-; or a pharmaceutically
acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C\,5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•C1-5 alkylcarbonyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
■mono-C1-5 alky lam inocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•carbocyclic arylcarbonylamino,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by substituent(s) independently selected from the
group consisting of:
••carbocyclic aryl, and
••carbocyclic aryl substituted by halogen,
•heterocyclylthio,
•heterocyclylthio substituted by C1-5 alkyl,
•C3-6 cycloalkyl,

136
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
"halogen,
"C1-5 alkyl,
••C2-5 alkenyl, and
••C7.5 alkenyl substituted by substituent(s) independently selected
from the group consisting of;
"•carbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
"hydroxy,
■•nitro,
••C1-5 alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
•"oxo, and
•••heterocyciyl,
••C1-5 alkoxy,
"carbocyclic aryloxy,
••carbocyclic aryl, and
••heterocyciyl,
•heterocyciyl, and
•heterocyciyl substituted by substituent(s) independently selected from the
group consisting of:

137
"C,_5 alkyl,
"C1-5 alkoxy, and
••carbocyclic aryl,
(ii) C2-5 alkenyl, and
C2-5 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by nitro,
(iii) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by carbocyclic aryl,
(iv) carbocyclyl,
(v) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••oxo, and
••carbocyclic aryl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and

138
••carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•C2.5 alkynylcarbonylamino,
•C2_5 alkynylcarbonylamino substituted by carbocyclic aryl,
•(carbocyclic aryl)NHC(O)NH,
•(carbocyclic aryl)NHC(O)NH substituted by C1-5 alkoxy, and
•(carbocyclic aryl)NHC(O)NH substituted by haloganated Q.5 alkoxy,
(vi) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C1-5 alkylthio,
"C1-5 alkylthio substituted by carbocyclic aryl,
••C1-5 alkylthio substituted by halogenated carbocyclic aryl,
••carbocyclic aryl, and
••heterocycly!,

139
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by Cj_5 alky!,
•C1-5 alkylthio,
•carbocyclic aryl,
•carbocyciic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
—nitro, and
»C1-5 alkyl,
•heterocyclyl;
wherein carbocyclic aryl is phenyl;
carbocyclyl is 1-oxo-indanyl or indenyl;
heterocyclyl is 1,2,3-triazolyl, l//-indolyl, li/-pyrrolyl,
2,3-dihydro-l-oxo-isoindolyl, 2-oxo-benzopyranyl, benzo[2,l,3]oxadiazolyl,
benzo[l,2,5]oxadiazolyl, furyl, isoxazolyl, morpholino, pyrazolyl, pyridyl, pyrimidyl,
quinolyl, quinoxaiyl, thiazolyl, or thienyl;
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Rt is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•oxo,
•Ci_s alkylcarbonyJoxy,
•carbocyclic aryloxy,
"carbocyclic aryloxy substituted by halogen,
•mono-C1-5 alkylaminocarbonyl,
-di-Ci,5 alkylaminocarbonyl,

140
•carbocyclic arylcarbonylamino,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
"C,_s alkyl,
••C2-5 alkenyl, and
"C2.5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••nitro,
••C1-5 alkyl, and
••C1-5 alkoxy,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
-d.s alkyl,
••C1-5 alkoxy, and
••carbocyclic aryl,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:

141
•halogen,
•hydroxy,
•cyano,
•nitro,
•C ,.5 alky I,
•C1-5 alky! substituted by substituent(s) independently selected from the
group consisting of:
"halogen, and
"OXO,
•Cj-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
*mono-C1-5 alkylaminocarbonyl,
*di-C1-5 alkylaminocarbonyl,
*mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•C2-5 alkynylcarbonylamino,
-C2-5 alkynylcarbonylamino substituted by carbocyclic aryi,
•(carbocyclic aryl)NHC(O)NH,
•(carbocyclic aryl)NHC(O)NH substituted by C^5 alkoxy, and
•(carbocyclic aryI)NHC(O)NH substituted by haloganated C1-5 alkoxy,
(iii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,

142
•C|_5 alkyl substituted by halogen,
•C1-5 alkyl substituted by heterocyclyl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C^ alkyl,
•C1-5 alkylthio,
•carbocyclic aryl,
•carbocyclic aryl substituted by halogen, and
"carbocyclic aryl substituted by nitro;
wherein carbocyclic aryl is phenyl;
carbocyclyf is indenyl;
heterocyclyl is l#-indolyl, l//-pyrrolyl, 2-oxo-benzopyranyl,
benzo[2,l,3]oxadiazolyl, benzo[l,2,5]oxadiazolyl, ruryl, isoxazolyl, morpholino,
pyridyl, quinoxalyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-3-
methoxybenzamide;
3-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)benzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2,l,3-
benzoxadiazole-5-carboxamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2'yl]amino}-
cyclohexyl)benzamide;
4-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-

143
cyclohexyl)benzamide;
4-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyI)-3-nitrobenzamide;
2-(4-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]-
amino}cyclohexyl)acetamide;
3-cyano-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyl)benzamide;
3,5-dichloro-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)benzamide;
3,4-dichloro-N-(cis-4-{[4-(dimethylamino)-5,6!7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7;8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2,2-
diphenylacetamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-3,4-
difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-cyC1-5hexyI)-3,5-
difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-4-
fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5?6,7,8-tetrahydroquinazolin-2-yJ]amino}-cyclohexyl)-3-
fluoro-5-(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-
hexanamide;
N-(cis-4- {[4-(dimethylamino)-5,6,7;8-tetrahydroquinazolin-2-yI]amino} -cyc!ohexyl)-4-
methyl-3-nitrobenzamide;
N-(cis-4-{[4-tdimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyC1-5hexyI)-3-
nitrobenzamide;
(2R)-N-(cis-4-{[4-(dimethylamino)-5T6,7,8-tetrahydroquinazolin-2-yI]amino}cyclohexyl)-2-

144
phenylcyclopropanecarboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyI)-2-
ph en oxybutanam ide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyC1-5hexyl)-2-
phenoxypropanam ide;
N-(cis-4-{[4-(dimethylamino)-5,6!7!8-tetrahydroquinazoIin-2-yl]amino}-cyclohexyl)-3-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yI]amino}-cyclohexyl)-4-
methy Ibenzam i de;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-cyC1-5hexyl)-3-
(trifluoromethoxy)benzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cy clohexy l)-3 -methylbenzam ide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-3-
iodobenzamide;
2-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyc lohexy l)-4-fluorobenzam ide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-cyclohexyl)-2-(3-
methoxyphenyl)acetamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-(4-
fluorophenyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyl)-2-(4-
meth oxypheny l)acetam ide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-5-
methyl-2-(trifluoromethyl)-3-fiiramide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2,5-
dimethyI-3-furamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-

145
cyclohexyl)-4-fluorobenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyI)-3-
fluoro-4-methylbenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyi)-3J5-
dimethoxybenzamide;
N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyC1-5hexyI)-3,5-
bis(trifiuoromethyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-4-
fluoro-3-methyIbenzamide;
2,5-dichloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexy])thiophene-3-carboxamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyl)-2-
(propylthio)nicotinamide;
l-benzyI-3-tert-butyl-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
ammo}cyclohexyl)-lH-pyrazole-5-carboxamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)nicotinamide;
2-[(cis-4- {[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino} -cyclohexyl)-
amino]-2-oxo-l -phenylethyl acetate;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyI)-
benzamide;
2-(benzyloxy)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)acetamide;
2-(4-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino}cyclohexyl)acetamide;
3-(2-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino}cyclohexyl)-5-methyItsoxazoIe-4-carboxamide;
l-(4-chloropheny!)-N-(cis-4-{[4-(dimethylamino)"5,6,7,8-tetrahydroquinazolin-2-yI]-

146
amino}cyclohexyl)cyclopentanecarboxamide;
3-(2-chloro-6-fluorophenyI)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-5-methylisoxazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyI)-l,3-
dimethy 1-1 H-pyrazole-5-carboxamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyl)-3-
fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyI)-4-
fluoro-3-(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethy)amino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-cyclohexyl)-5-
methyl-2-phenyi-2H-1,2,3-triazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyC1-5hexyl)-2-(4-
methoxyphenoxy)- 5 -n itrobenzam i de;
N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-5-
nitro-2-furamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyl)-2-
phenoxyacetam ide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-
quinoxaIine-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6?7,8-tetrahydroquinazolin-2-yl]amino}-cyC1-5hexyl)-3-
(trifluoromethy l)benzam ide;
2-(3-chIorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]-
amino}cyclohexyl)acetamide;
3-(2,6-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino}cyC1-5hexyl)-5-methyHsoxazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-
phenoxynicotinamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-(4-

147
methylphenoxy)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexy])-2-(2-
thienyl)-l,3-thiazole-4-carboxamide;
5-bromo-N-(cis-4-{[4-(dimethy!amino)-5,6?7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)thiophene-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-
(2,3,6-trichIorophenyi)acetamide;
2-(2-chloro-4-fluorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
y!]amino} cyclohexyl)acetamide;
5-(4"Chloro-2-nitrophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-furamide;
5-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyI)thiophene-2-carboxamide;
N-(cis-4-{t4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2,3-
d i pheny lpropanam ide;
N-(cis-4-{[4-(dimethylamino)-5,6,7;8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-3-(2-
hy droxypheny l)propanam ide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-5-
iodo-2-fliramide;
N-(cis-4-{[4-(dimethylamino)-5,657,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyI)-2-(2-
iodophenyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5!6,7)8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-(5-
methoxy-2-methyl-lH-indol-3-yl)acetamide;
N-(cis-4-{[4-(dimethylamino)'5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-cyclohexyl)-3-
oxoindane-1 -carboxamide;
2-benzyl-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)benzamide;
2,2-bis(4-chIorophenyl)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-

148
amino}cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-5-(4-
methyl-2-nitrophenyl)-2-furamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-y]]amino}-cyclohexyl)-5-
nitrothiophene-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyC1-5hexy])-3-
methyI-4-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-cyclohexyl)-3-
methoxy-4-nitrobenzamide;
3-acetyl-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)benzamide;
5-bromo-N-(cis-4-{[4'(dimethylamino)-5,6,7,8-tetrahydroqumazolin-2-yl]amino}-
cyc!ohexyl)-2-furamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-[(4-
methy 1 pyr imid in-2 -y l)th io] ac etam ide;
5-(4-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]-
amino}cyclohexyl)-2-furamide;
2-(3,4-dichlorophenyi)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino} cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyl)-2-(4-
hydroxy-3,5-dimethoxyphenyl)acetamide;
4,5-dibromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)thiophene-2-carboxamide;
N2,N6-dibenzoyl-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazo]in-2-yl]amino}-
cyclohexyl)lysinamide;
3-(dimethylamino)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino}cyclohexyl)benzamide;
4,5-dibromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-

149
cyclohexy])-2-furamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-4-(4-
fluorophenyl)-4-oxobutanamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyI)-2-(2-
fluorobiphenyl-4-yI)propanamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquina2olin-2-yI]amino}-cyC1-5hexyI)-2-[4-
(1-oxo-l, 3 -dihydro-2H-isoindol-2-yl)phenyl]propanamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-(lH-
indoI-3-yI)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-(7-
methoxy-2-oxo-2H-chromen-4-yl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7:,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-(lH-
indol-3-yl)-4-oxo-4-phenylbutanamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-3,5-
dimethyI-2-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-benzamide;
3,5-dichloro-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-[(3-pheny!prop-2-ynoyl)amino]benzamide;
4-(4-tert-butylphenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino} cyclohexyl)-2-(7-ethyl-1 H-indoI-3-yI)-4-oxobutanamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-(l-
methyl-lH-indol-3-yl)-4-(4-methylphenyl)-4-oxobutanamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroqutnazoJin-2-yI]amino}-cyclohexyl)-2-
methyI-l-(3-morpholin-4-ylpropyl)-5-phenyI-lH-pyrrole-3-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyI)-4-(4-
n itropheny l)butan am id e;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyI)-2-(3-
phenoxypheny l)ac etam i de;
N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-y]]amino}-cyC1-5hexyl)-2-(4-

150
phenoxyphenyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6?7,8-tetrahydroquinazoIin-2-yl]amino}-cyc!ohexyl)-2-(2-
phenyl-1 H-indol-3-yl)acetamide;
N2-benzoyl-N5-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquina2olin-2-yl]amino}-
cyC1-5hexyO-N^N'-dipropylglutamamide;
N-(cis-4-{[4-(dimethyIamino)-556,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyl)-3-
phenoxybenzaraide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyI)-2-
(ethylthio)-2,2-diphenyIacetamide;
N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yI]amino}-cyC1-5hexyl)-N,N-
bis[(lS)-l-phenylethyl]phthaIamide;
(2S)-N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}cyclohexyl)-2-
(2-fluorobiphenyl-4-yl)propanamide;
2-[(4-chlorobenzyl)thio]-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino}cyclohexyl)-4-(4-methylphenyI)-4-oxobutanamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-
{(1 E)-5-fluoro-2-methyI-l -[4-(methylsuIfinyl)benzylidene]-1 H-inden-3-yl} acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-[4-
(2-thienylcarbonyl)phenyI]propanamide;
3-(benzyloxy)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cy c lohexy l)-4 -meth oxybenzam ide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-cyclohexyl)-2-
methyl-1,5-diphenyl-l H-pyrrole-3-carboxamide;
l-{2-[(2-chloro-6-fluorobenzyl)thio]ethyI}-N-(cis-4-{[4-(dimethylamino)-5!6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyI)-2-methyl-5-phenyl-I H-pyrrole-3-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-
phenoxy benzam ide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-

151
phenylquinoline-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyC1-5hexyl)-5-(3-
nitrophenyl)-2-furamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-cyclohexyI)-5-
nitrothiophene-3-carboxamide;
N-(cis-4- {[4~(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino} -cyclohexyl)-1 -
methyI-4-nitro-lH-pyrrole-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-
methoxy-4-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyC1-5hexyl)-2-
methoxy-2 -pheny lacetam ide;
5-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2~yl]amino}-
cyclohexyI)-2-hydroxybenzamide;
3-bromo-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)methyl]benzamide;
N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-
methyl] -2-(ethy 1th io)n ic otinam ide;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-
methyl]-2-(4-methoxyphenyl)acetamide;
N-Etcis^-f^-tdimethylaminoVS^^^-tetrahydroquinazolin^-y^aminoj-cyclohexyl)-
methyI]-5-methyl-2-(trifIuoromethyI)-3-furamide;
(2E)-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)-
methyl]-3-(4-nitrophenyl)acryIamide;
N-[(cis-4-{[4-(dimethyJamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-
methyl]-4-fluoro-3-methylbenzatnide;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-
methyl]-2-(propylthio)nicotinamide;
2,6-dichloro-N-[(cis-4-{[4-(dtmethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-

152
cyclohexyl)methyl]benzamide;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazo]in-2-yl]amino}-cyclohexyl)-
methyl]-2,4,6-trimethylbenzamide;
2-chloro-N-[(cis-4-{[4-(dimethylamino)-5,6;7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyI)methy]]-6-fluorobenzamide;
2,4,6-trichloro-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)methyl]benzamide;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-
methyl]-2-(2,3,6-trichlorophenyl)acetamide;
(2E)-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)-
methyl]-3-(3-nitrophenyl)acrylamide; and
N-[cis-4-(4-dimethylamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-cyclohexylmethyl]-
3,4-difluoro-benzamide;
or a pharniaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyC1-5hexyl)-3-
methoxybenzamide;
3-bromo-N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquina2olin-2-yl]amino}-
cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2,l,3-
benzoxadiazole-5-carboxamide;
3-chloro-N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyi)benzamide;
4-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)benzamide;
4-chloro-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-3-nitrobenzamide;

153
2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino}cyclohexyl)acetamide;
3-cyano-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)benzamide;
3,5-dichIoro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)benzamide;
354-dichloro-N-(cis-4-{[4-tdimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2,2-
diphenylacetarnide;
N-(cis-4-{[4-(dimethyIamino)-556,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-3,4-
difluorobenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-3,5-
difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-4-
fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyl)-3-
fluoro-5-(trif!uoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6r7,8-tetrahydroquinazoiin-2-yl]amino}-cyclohexyl)-4-
methyl-3-nitrobenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-3-
nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyC1-5hexyl)-2-
phenoxybutanamide;
N-(cis-4-{[4-(dimethylamino)-5?6,7;8-tetrahydroquinazolin-2-yI]amino}-cyc]ohexyl)-2-
phenoxypropanamide;
N-(cis-4-{[4-(dimethylamino)-5;6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-3-
methylbenzamide;

154
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl}amino}-cyclohexy])-3-
iodobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-cyclohexyl)-2-(4-
fluorophenyl)acetamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2,5-
dimethyI-3-furamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyl)-4-fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-3,5-
d i methoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-3,5-
bis(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)~5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyC1-5hexyl)-4-
fluoro-3-methylbenzamide;
2,5-dichIoro-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)thiophene-3-carboxamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)nicotinamide;
2-[(cis-4-{[4-(dimethy]amino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyC1-5hexyl)-
amino]-2-oxo-1 -phenylethyl acetate;
3-(2-chIoro-6-fluorophenyI)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,84etrahydroquinazolin-2-
yl]amino}cyclohexyI)-5-methylisoxazo!e-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5!6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-3-
fl u orobenzam ide;
N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazo]in-2-yl]amino}-cyclohexyl)-4-
fluoro-3-(trifluoromethy])benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-cyclohexyl)-2-(4-
methoxyphenoxy)-5-nitrobenzamide;

155
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yi]amino}-cyclohexyl)-5-
nitro-2-furamide;
N-(cis-4-{[4-(dimethylamino)-5,6;7;8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-
phenoxyacetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoiin-2-yl]amino}-cyclohexyl)-
quinoxaline-2-carboxamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyl)-3-
(trifluoromethyl)benzamide;
2-(3-chlorophenoxy)-N-(cis-4-{[4'(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yI]-
amino}cyclohexyl)acetamide;
3-(2,6-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino}cyclohexyl)-5-methylisoxazoIe-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyC1-5hexyl)-2-(4-
methylphenoxy)nicotinamide;
2-(2-chloro-4-fluorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)acetamide;
5-(4-chloro-2-nitrophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yljamino} cyclohexyl)-2-fiiramide;
5-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cy c lohexy l)th ioph ene-2-carboxam ide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-5-
iodo-2-furamide;
2,2-bis(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino} cyclohexyl)acetamtde;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyi)-5-
nitrothiophene-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6;7,8-tetrahydroquinazolin-2-yl]amino}-cycbhexyl)-3-
methyl-4-nitrobenzamide;

156
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyl)-3-
methoxy-4-nitrobenzamide;
3-acetyl-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)benzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyI)-2-furamide;
5-(4-chlorophenyI)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino}cyclohexyl)-2-furamide;
2-(3,4-dichiorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino} cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-(4-
hydroxy-3,5-dimethoxyphenyl)acetamide;
4,5-dibromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-furamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyI)-2-(lH-
indoI-3-yl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-(7-
methoxy-2-oxo-2H-chromen-4-yl)acetamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-3,5-
dimethyl-2-[( {[4-(trifluoromethoxy)phenyI]amino} carbonyl)amino]-benzamide;
3,5-dichloro-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-[(3-phenylprop-2-ynoyl)amino]benzamide;
4-(4-tert-butylphenyl)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino}cyclohexyi)-2-(7-ethyl-lH-indo]-3-yI)'4-oxobutanamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-yI]amino}-cyclohexyl)-2-
methyl-l-(3-morphoIin-4-yIpropyl)-5-phenyl-lH-pyrrole-3-carboxamide;
N-(cis-4-{[4-(dimethyIamino)-5;6,7,8-tetrahydroquinazolin-2~yl]amino}-cyclohexyl)-4-(4-
nitrophenyl)butanamide;

157
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-(2-
phenyl-lH-indol-3-yl)acetamide;
N2-benzoy]-N5-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyO-N^N'-dipropylglutamamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,S-tetrahydroquinazolin-2-yI]amino}-cyclohexyl)-3-
phenoxybenzamide;
N'-(cis-4-{[4-(dimethy]amino)-5,6,7,8-telrahydroquinazoIin-2-y]]amino}-cyC1-5hexy])-N,N-
bis[(lS)-l-phenylethyl]phthalamide;
N"(cis-4-{[4-(dimethylamino)-5,6,7?8-tetrahydroquinazolin-2-yl]amino}-cyC1-5hexyl)-2-
{(lE)-5-fluoro-2-methyl-l-[4-(methylsulfmyI)benzyIidene]-lH-inden-3-yl}acetamide;
3-(benzyloxy)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexy])-4-methoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-2-
phenoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7?8-tetrahydroquinazolin-2-yl]amino}-cyclohexyI)'5-
nitrothiophene-3-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-cyclohexyl)-l-
methyI-4-nitro-lH-pyrrole-2-carboxamide;
5-chIoro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyc lohexy I)-2-hy droxybenzam ide;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}'Cyclohexyl)-
methyl]-2-(ethylthio)nicotinamide;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyI)-
methy!]-2-(4-methoxyphenyl)acetamide;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-cyclohexyl)-
methyl]-5-methyl-2-(trifluoromethyI)-3-furamide;
N-[{cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-
methyI]-2-(propylthio)nicotinamide; and

158
2,4,6-trichloro-N-[(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyl)methyl]benzamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R[ is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
"OXO,
•C1-5 alkoxy carbonyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C,_5 alkyl,
••C2-5 alkenyl, and
••C1-5 alkoxy,
•Cu alkylthto, and
•heterocyclyl,
(ii) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by carbocyclic aryl,
(iii) carbocyclyl,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•cyano,
•nitro,
•do alkyl,

159
•C|.5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
"halogen,
"oxo? and
"carbocyclic aryl,
*C1-5 alkoxy carbonyl,
•C^ alkoxy,
•C,_7 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
"halogen, and
••carbocyclic aryl,
*C3-6 cycloalkoxy,
'carbocyclic aryloxy,
•mono-C1-5 alkylamino,
*di-C1-5 alkylamino,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by halogen, and
•carbocyclic aryl,
(v) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy carbonyl
•C1-5 alkoxy carbonyl substituted by carbocyclic aryl, and
•carbocyclic aryl;
L is Formula (VII);

160
Y is -C(O)NR5-;
wherein carbocyclic aryl is phenyl or naphthyl;
carbocyclyl is indanyl, adamantly, or 9#-fluorenyl;
heterocyclyl is 2,3-dihydro-benzo[I,4]dioxinyl,
3,4-dihydro-2#-benzo[b][l,4]dioxepinyl, 4#-benzo[l,3]dioxinyl,
benzo[l,3]dioxolyl, furyl, isoxazolyl, piperidyl, pyridyl, orthienyl;
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-: R5 is hydrogen; or a
pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•C1-5 alkoxy carbonyl,
•carbocyclic aryl, and
■carbocyclic aryl substituted by halogen,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy, and
•C1-5 alkoxy substituted by halogen,
(iii) heterocyclyl, and

161
heterocyclyl substituted by C1-5 alky I, and
heterocyclyl substituted by carbocyclic aryl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is isoxazolyl;
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
N-(cis-4-{[4-(dimethylamino)-5,657J8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-(2-
ethyI-6-methylphenyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-(4-
fluorophenyl)urea;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-
mesitylurea;
N-(cis-4-{[4-(dimethylamino)-5T6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-
(2,4,6-trichlorophenyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-
(2,4,6-tr ibromopheny I)urea;
N-(254-dibromo-6-fluorophenyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]arnino}cyclohexyl)urea;
N-(2,6-diethylphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino}cyclohexyl)urea;
N-(2-chlorobenzyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino} cyclohexyl)urea;
N-(cis-4-{[4-(dimethytamino)-5,6,7;,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-(2-
ethy 1 -6-i sopropy lph eny I)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-(2-
ethylphenyl)urea;

162
N^cis^-l^-tdimethylamino^S^JjS-tetrahydroquinazolin^-yljaminoJ-cyC1-5hexy^-N'-tS-
isopropyl-6-methylphenyl)urea;
N-(2-tert-butyl-6-methylphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyC1-5hexyl)-N'-
(diphenylmethyl)urea;
N-(4-bromo-2,6-dimethylphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-(3-
methyl-5-phenylisoxazol-4-yl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyC1-5hexyI)-N'-l-
naphthylurea;
N-(cis-4-{[4-(dimethyIamino)-5,6)7,8-tetrahydroquinazolin-2-yl]amino}-cyc]ohexyl)-N'-[l-
(l-naphthyl)ethyl]urea;
N-(2,4-dibromophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino} cyclohexyl)urea;
N-(2,4-dichlorobenzyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]-
amino}cyclohexyl)urea;
N-(2,4-dimethoxyphenyI)-N'-(cis-4-{[4-(dimethylaraino)-5,6,7)8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-(2-
ethoxyphenyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-(2-
fluorobenzyl)urea;
N-(cis-4-{[4-(dimethylamino)-5)6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyl)-Nl-
(3,4,5-trimethoxyphenyl)urea;
N-(3,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)urea;

163
N-(4-chloro-2-methylphenyl)-N'-(cis-4-{[4-(dimethy]amino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yI]amino}-cyclohexyl)-N'-(4-
fluorobenzyl)urea;
N-(cis-4-{[4-tdimethy]amino)-5,6,7,8-tetrahydroquinazoIin-2-yI]amino}-cyC1-5hexyl)-N'-(4-
methoxy-2-methyl phenyl)urea;
N-(5-chloro-2,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyc!ohexyl)urea;
N-[l-(4"bromophenyI)ethyI]-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)urea;
N-(4-bromo-2-methylphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yl]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6;7,8-tetrahydroquinazoIin-2-yl]amino}-cyclohexyl)-N'-(5-
methyl-3-phenylisoxazol-4-yl)urea;
N-(2,3-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino} cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-(4-
methylphenyl)urea;
N-(2,6-diisopropyiphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-
(2,4,5-trichlorophenyl)urea;
N-(2,5-dimethoxyphenyI)-N'-(cis-4-{[4-tdimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino} cyclohexy l)urea;
N-(4-bromo-2-chlorophenyl)-N'-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yljamino} cyclohexyl)urea;
N-(cis-4-{[4-{dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}cyclohexyl)-N'-[2-
(trifluoromethoxy)phenyl]urea;

164
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-
methyl]-N'-(2,6-dimethylphenyI)urea;
N-(254-difIuorophenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]-
amino}cyclohexyl)methyl]urea;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-
methyl]-N'-(2-ethyl-6-methylphenyl)urea;
ethyl N-( {[(cis-4- {[4-(dimethy lamino)-5,6,7,8-tetrahydroquinazolin-2-y l]-amino} -
cyclohexyl)methyl]amino}carbonyl)Ieucinate;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-
methyl]-N'-(4-fiuorophenyl)urea;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-
methy 1] -N'-mes ity lu rea;
N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-
methy 1] -N'-(2,4,6-trich loropheny I)urea;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyl)-
methyl]-N'-(2,4,6-tribromophenyl)urea;
N-(2,6-diethylphenyl)-Nt-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]-
amino}cyclohexyl)methyl]urea;
N-[2-chloro-6-(trifluoromethyl)phenyl]-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyC1-5hexyl)methyl]urea;
N-(2-chloro-6-methyIphenyl)-N'-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-
2-yl]amino}cyclohexyl)methyl]urea;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,84etrahydroquinazolin-2-yl]amino}-cyclohexyl)-
methyl]-N'-(2-ethyl-6-isopropylphenyl)urea;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyC1-5hexyl)-
methyl]-N'-(2-isopropyl-6-methylphenyI)urea;
N-(2-tert-butyl-6-methyIphenyI)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)methyl]urea;

165
N-(2-tert-butyIphenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yi]-
amino}cyclohexyl)methyi]urea;
N-(3-chIoro-2-methylphenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-
2-yl]amino}cyC1-5hexyI)methyl]urea;
N-(4-bromo-2,6-dimethy]phenyI)-Nl-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyI)methyI]urea;
N-(2,6-diisopropyIphenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyc!ohexyl)methyl]urea;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-
methyl]-N'-(2,3-dimethyl-6-nitrophenyI)urea;
N-(2,6-dibromo-4-fluorophenyl)-N'-[(cis'4-{[4-(dimethylamino)-5,6;7,8-
tetrahydroquinazolin-2-yI]amino}cyc!ohexyl)methyl]urea;
N-(2?6-dichlorophenyI)-N'-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino} cyclohexyl)methyl]urea; and
l-(2,3-dichIoro-phenyI)-3-[cis-4-(4-dimethy)amino-5,6,7,8-tetrahydro-quinazolin-2-
y lam i no)-cy c Iohexy Imethy l]-urea;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R^ is selected from the group consisting of:
(i) Ci-8 alkyl, and
Ci_8 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•mono-C1-5 alkylamino,
•di-Cj.5 alkylamino,
•C3-6 cycloalkyi,
•C3-6 cycloalkenyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:

166
"halogen,
••C1-5 alky], and
••Ci.s alkoxy,
•heterocyclyl,
(ii) C7.5 alkynyl,
(iii) C2.5 alkenyl,
(iv) C3.12 cycloalkyl,
(v) carbocyclyl,
(vi) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•cyano,
•nitro,
•CHoaIkyl,
•C1.10 alky] substituted by substituent(s) independently selected from the
group consisting of:
"halogen, and
"OXO,
•carboxy,
•C1-5 alkoxy carbonyl,
•C]-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
"halogen, and
••carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by nitro,

167
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•C1-5 alkoxy carbonylamino,
•carbocyclic aryl azo,
•carbocyclic aryl azo substituted by substituent(s) independently selected
from the group consisting of:
••mono-C1-5 alkylamino, and
••di-Cj.g alkylamino,
"C1-5 alkylthio,
•C1-5 alkylthio substituted by halogen,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by nitro,
•amino sulfonyl,
•heterocyclyl sulfonyl,
•C3-6 cycloalkyl,
*C3-6 cycloalkyl substituted by C1-5 alkyl.,
•carbocyclic aryl, and
•heterocyclyl,
(vii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkyl,
•C1-5 alkoxy carbonyl,
•carbocyclic aryloxy,
•carbocyclic aryl, and
•heterocyclyl;
L is Formula (VII);
Y is -C(S)NR5-;

168
wherein carbocyclic aryl is phenyl or naphthyl;
carbocyclyl is indanyl, bicyclo[2,2.1]heptyl, bicyclo[2.2.1]heptenyi, or
adamantly;
heterocyclyl is 2,3-dihydro-benzo[l,4]dioxinyl,
4,5,6,7-tetrahydro-benzo[b]thienyl, benzo[l,3]dioxolyl, benzo[2,l,3]thiadiazolyl,
fury], isoxazolyl, morpholinyl, oxazolyl, phenanthro[9,10-d]oxazolyl, piperidyl,
pyrazolyl, pyridyl, tetrahydrofuryl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH?-: R5 is hydrogen; or a
pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R] is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by carbocyclic aryl,
(ii) carbocyclic ary!, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy,
*C1-5 alkoxy substituted by halogen,
•mono-C]-5 alky lam ino, and
•di-Cto alkylamino;
wherein carbocyclic aryl is phenyl or naphthyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.

169
In some embodiments, compounds of the present invention are of Formula ([) wherein the
compound is selected from the group consisting of:
N-(2,4-dimethoxyphenyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)thiourea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-
(3,4,5-trimethoxyphenyl)thiourea;
N-(354-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)thiourea;
N-[4-(dimethylamino>l-naphthyl]-N'-(cis-4-{[4-(dimethylamino)-5,6,758-
tetrahydroquinazolin-2-yl]amino}cyclohexyI)thiourea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-(2-
methoxy-5-methylphenyl)thiourea;
N-(4-bromo-2-chIorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazo]in-2-
yljamino} cyclohexyl)thiourea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-cyclohexyl)-N'-(4-
iodophenyl)thiourea;
N-(cis-4-{[4-(dimethylamino)-55657,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-
(2,4,6-tribromophenyl)thiourea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-
(2,4,6-trichlorophenyI)thiourea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2 -yljamino} -cyclohexyl)-N'-
mesitylthiourea;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquina2olin-2-yl]amino}-cyC1-5hexyl)-N'-
(2,4-dimethylphenyI)thiourea;
N-(2;6-diethyiphenyl)-N'-(cis-4-{[4-(dimethylamino)-5?6,7,8-tetrahydroquinazolin-2-yl]-
amino}cyclohexyl)thiourea;
N-(4-bromo-2,6-dimethylphenyl)-N'~(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-y)]amino}cyclohexyl)thiourea;

170
N-(4-bromo-2-methylphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yl]amino}cyC1-5hexyI)thiourea;
N-[4-bromo-2-(trifluoromethyI)phenyl]-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea;
N-(4-chloro-2-methylphenyI)-N'-(cis-4-{[4-(dimethy]amino)-5,6,7,8-tetrahydroquinazoIin-2-
y l]amino} cyclohexyl)thiourea;
N-[4-chloro-2-(trifIuoromethyI)phenyI]-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]arnino}cyclohexyl)thiourea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-(4-
fluoro-2-methylphenyl)thiourea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyclohexyl)-N'-(4-
methoxy-2-methyIphenyl)thiourea;
N-(5-chloro-2,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyI)thiourea;
N-(2,4-dibromo-6-fluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yI]amino}cyclohexyI)thiourea;
N-(2,4-dichioro-6-methylphenyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)thiourea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-cyclohexyl)-N'-(2-
ethoxyphenyl)thiourea;
N-[4-bromo-2-(trifluoromethoxy)phenyl]-N'-(cis-4-{[4-tdimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyi)thiourea;
N-{4-ch]oro-2,5-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)thiourea; and
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-cyC1-5hexyI)-N'-
(2,2-diphenylethyl)thiourea;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R] is selected from the group consisting of:

171
(i) C^8 alkyl, and
Ci_8 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•halogen,
"C1-5 alkoxy,
*Ct_5 alkoxy substituted by carbocyclic aryl,
•carbocyclyl,
•carbocyclic aryl,
•carbocyclic aryi substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
"C1-5 alkoxy,
(ii) C2-5 alkenyl,
(iii) carbocyclyl,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen, and
•C1-5 alkoxy;
L is Formula (VII);
Y is -C(O)O-;
wherein carbocyclic aryl is phenyl or naphthyl;
carbocyclyl is 9#-fluorenyl or menthyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.

172
In some embodiments of the present invention, R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH?-; or a pharmaceutically
acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Q is Formula (IV); p is 0;
Ri is selected from the group consisting of:
(i) Ci_g alkyl, and
Ci_8 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•halogen,
•oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•C1-5 alkylcarbonyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryioxy substituted by nitro,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•heterocyclyloxy,
•heterocyelyloxy substituted by C1-5 alkyl,
•Cj.s alkoxycarbonyl,
•mono-C1-5 alkylaminocarbonyl,
•di-Cj.5 afkylaminocarbonyl,
•mono-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•mono-Ct_5 alkylamino substituted by carbocyclic aryl,
*di-C1-5 alkylamino,
•di-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino substituted by carbocyclic aryl,

173
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by C1-5 alkyl,
•di-carbocyclic arylamino,
•di-carbocyclic arylamino substituted by C1-5 alkyl,
•C1-5 alkoxycarbonylamino,
•carbocyclic arylcarbonylamino,
•C|.5 alkylthio,
"C1-5 alkylthio substituted by substituent(s) independently selected from the
group consisting of:
"carbocyclic aryl,
••carbocyclic aryl substituted by halogen, and
••carbocyclic aryl substituted by C1-5 alkoxy,
•carbocyclic arylthio,
•heterocyclylthio,
•heterocyclylthio substituted by nitro,
•heterocyclylthio substituted by C1-5 alkyl,
•C3^ cycloalkyl,
•C3-6 cycloalkenyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
»C1-5 alkyl,
••C1-5 alkoxy,
•*C2-5 alkenyl, and
"C2-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and

174
•••carbocyclic aryl substituted by C1-5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••nitro,
-•C1-5 alky],
••C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
—oxo,
•••carbocyclic aryl, and
"•heterocyclyl,
"C2-5 alkenyl,
••C1-5 alkoxy,
**C1-5 alkoxy substituted by halogen,
••C1-5 alkoxy substituted by carbocyclic aryl,
"carbocyclic aryloxy,
"carbocyclic aryl, and
••heterocyclyl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5 alkyl,
••C1-5 alkyl substituted by carbocyclic aryl,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryl, and

175
'•carbocyclic aryl substituted by halogen,
(ii) C2-7 alkenyl, and
C2_7 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
•nitro, and
"C1-5 alkoxy,
(iii) C2-5 alkynyl, and
C?.5 alkynyl substituted by carbocyclic aryl,
(iv) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by substituent(s) independently selected from the
group consisting of:
•d.s alkyl,
•C1-5 alkyl substituted by oxo,
•C1-5 alkyl substituted by carbocyclic aryl, and
•carbocyclic aryl,
(v) carbocyclyl,
(vi) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
•Ci.s alkyl,

176
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
"halogen,
"OXO,
"carbocyclic aryloxy,
•"carbocyclic aryl, and
"carbocyclic aryl substituted by C1-5 alkyl,
•C1-5 alkoxy,
•Ci-s alkoxy substituted by substituent(s) independently selected from the
group consisting of:
"halogen,
••carbocyclic aryl, and
"halogenated carbocyclic aryl,
•C2-g alkenyloxy,
•C3.fi cycloalkoxy,
"carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•C],5 alkoxycarbonyl,
•mono-C1-5 atkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-Cj.j alkyl ami noc arbonyl substituted by carbocyclic aryl,
•amino,
*mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino substituted by cyano,
•C2-5 alkynylcarbonylamino,

177
•C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,
•(carbocyclic aryl)NHC(O)NH,
•(carbocyclic aryI)NHC(O)NH substituted by C1-5 alkoxy,
•(carbocyclic aryI)NHC(O)NH substituted by haloganated C1-5 alkoxy,
•C1-5 aikylthio,
•C,.,- aikylthio substituted by halogen,
'carbocyclic arylthio,
•carbocyclic arylthio substituted by cyano,
"mono-C1-5 alkylaminosulfonyl,
•di-C1-5 alkylaminosulfonyl,
•carbocyclic aryl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
-C1-5 alkyl,
••carbocyclic aryl, and
•halogenated carbocyclic aryl,
(vii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
"hydroxy,
••C1-5 aikylthio,

178
"C1-5 alkylthio substituted by carbocyclic aryl,
••Cj.5 alkylthio substituted by halogenated carbocyclic aryl,
"carbocyclic aryl,
"carbocyclic aryl substituted by halogen, and
••heterocyclyl,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by Cj_5 alkyl,
•C,_5 alkylthio,
•C2-5 alkenylthio,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by Ct_5 alkoxycarbonyl,
"Cj-5 alkylsulfonyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by C1-5 alkyl,
•Ct_5 alkoxycarbonyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
••nitro,
'•C1-5 alkyl, and
•"C1-5 alkyl substituted by halogen,
•heterocyclyl;
wherein carbocyclic aryl is phenyl, naphthyl, or anthranyl;
carbocyclyl is 1,2,3,4-tetrahydronaphthyl, 1-oxo-indanyl, 9-fluorenyl,
9-oxo-9//-fIuorenyI, bicyclo[2.2.1]heptyl, indenyl, or menthyl;
heterocyclyl is 1,2,3-triazolyl, \H-'mdo\y\, l//-pyrrolyl,

179
2,3-dihydro-l-oxo-isoindoly], 2,3-dihydro-benzo[l,4]dioxinyl,
2,3-dihydro-benzofuryl, 2,4-dihydro-3-oxo-pyrazolyl, 2#-benzopyranyl.
2-oxo-benzopyranyl, 3,4-dihydro-2//-benzo[b][l,4]dioxepinyl,
4-oxo-l,5,6,7-tetrahydro-indolyl, 4-oxo-benzopyranyl, 9#-carbazolyl, 9//-xanthenyl,
benzo[l,3]dioxolyl, benzo[2,l,3]oxadiazolyl, benzo[l,2,5]oxadiazolyl,
benzo[b]thienyl, benzofuryl, benzothiazolyl, fury!, imidazo[2,l-b]thiazolyl,
imidazolyl, isoxazolyl, morpholino, pyrazolyl, pyridyl, pyrimidyl, quinolyl,
quinoxalyl, thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R, is selected from the group consisting of:
(i) C]-7 alkyl, and
C1-7 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•mono-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by substituent(s) independently selected
from the group consisting of:
••cyano, and
"carbocyclic aryl,
•di-C1-5 alkylamino,
•di-C1-5 alkylamino substituted by substituent(s) independently selected from
the group consisting of:
••cyano, and
••carbocyclic aryl,

180
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by C1-5 alkyl,
•di-carbocyclic arylamino substituted by C1-5 alky],
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
••Cj.5 alkyi, and
••C1-5 alkoxy,
(ii) C2-7 alkenyl, and
C2-7 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by C1-5 alkoxy,
(iii) C7.5 alkynyl, and
C2-5 alkynyl substituted by carbocyclic aryl,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•cyano,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:

181
••halogen,
"carbocyclic aryl, and
"carbocyclic aryl substituted by halogen,
*C2-5 alkenyloxy,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-Cj.s alkylamino substituted by cyano,
•di-Cj.5 alkylamino substituted by cyano,
•C1-5 alkylthio, and
•C1-5 alkylthio substituted by halogen,
(v) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
■C1-5 alky],
•C1-5 alkyl substituted by hydroxy,
•C1-5 alkoxy,
'carbocyclic arylthio,
•carbocyclic arylthio substituted by C1-5 alkoxycarbonyl,
•C1-5 alkoxycarbonyl,
'carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
•*C1-5 alkyl, and
**C1-5 alkyl substituted by halogen;
L is Formula (VII);
Y is a single bond or -CH2-;

182
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is l//-indolyl, 1/f-pyrrolyl, 2!3-dihydro-benzo[l,4]dioxinyl,
4-oxo-benzopyranyl, 9//-carbazoIyI, benzo[l,3]dioxolyl, benzo[b]thienyl, furyl,
imidazo[2,l-b]thiazolyl, pyrazolyl, pyridyl, orthienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R2 is methylamino, or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-; or a pharmaceutically
acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Rj is selected from the group consisting of:
(i) C2.5 alkenyl, and
C2-5 alkenyl substituted by carbocyclic aryl,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
"halogen,
•hydroxy,
•C1-5 alkyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
—halogen,
••carbocyclic aryl, and
••carbocyclic aryl substituted by halogen,
•C2-5 alkenyloxy,
•mono-C1-5 alkylamino,
•di-C]-g alkylamino,
*mono-C1-5 alkytamino substituted by cyano, and

183
*di-C1-5 alkylamino substituted by cyano,
(iii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkyl,
•C1-5 alkoxy,
•C1-5 alkoxycarbonyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
"C1-5 alkyl, and
"C1-5 alkyl substituted by halogen;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is l//-indolyl, 9//-carbazolyI, benzo[l,3]dioxolyl, pyrazolyl, or
pyridyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R] is selected from the group consisting of:
(i) C2_5 alkenyl, and
C2-5 alkenyl substituted by carbocyclic aryl,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•C1-5 alkyl,

184
•C1-5 alkoxy,
"C1-5 alkoxy substituted by halogen,
*C2-5 alkenyloxy,
(iii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C,-s alkyl,
•C1-5 alkoxy,
•C1-5 alkoxycarbonyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by C1-5 alkyl, and
•carbocyclic aryl substituted by halogenated C1-5 alkyl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is l/f-indolyl, 9//-carbazolyl, benzo[l,3]dioxolyl, or
pyrazolyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
N2-(cis-4-{[(5-bromo-lH-indol-3-yl)methyl]amino}cyclohexyl)-N4,N4-dimethylpyrimidine-
2,4-diamine;
N2-[cis-4-({[5-(4-fluorophenyl)pyridin-3-yl]methyl}amino)cyclohexyl]-N4,N4-
dimethylpyrimidine-2,4-diamine;
ethyl 4,6-dichloro-3-{[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)-
amino]methyl}-lH-indole-2-carboxyIate;
N2-(cis-4-{[(2,6-dimethoxybenzy!)amino]methyI}cyclohexyl)-N4,N4-dimethylpyrimidine-
2,4-diamine;

185
N""-(cis-4-{[(2-ethoxybenzyI)amino]methyl}cyclohexyl)-N4,N4-dimethylpyrimidine-2,4-
diamine;
N2-[cis-4-({[(4-methoxy-l-naphthyl)methyl]amino}methyl)cyclohexyl]-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-[cis-4-({[(5-methoxy-lH-indoI-3-yl)methyl]amino}methyl)cyclohexyl]-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-[cis-4-({[(2-methoxy-l-naphthyl)methyl]amino}methyl)cyclohexyI]-N4,N4-
dimethyIpyrimidine-2,4-diamine;
4-bromo-2-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)methyl]-
amino}methyi)-6-methoxyphenol;
N2-[cis-4-({[(5-bromo-lH-indoI-3-yl)methyl]amino}methyl)cyclohexyl]-N4,N4-
dimethylpyrimidine-2;4-diamine;
N2-(cis-4-{[(2,4-dimethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-dimethylpyrimidine-
2,4-diamine;
N4)N4-dimethyl-N2-(cis-4-{[(2,3,4'trimethoxybenzyl)araino]methyl}-cyC1-5hexyl)pyrimidine-
2,4-diamine;
N2-(cis-4-{[(3-ethoxy-4-methoxybenzyl)amino]methyl}cyclohexyI)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[({3-[4-(trifluoromethyI)phenyl]-lH-pyrazol-4-y!}methyl)-
amino]methyl}cyclohexyI)pyrimidme-2,4-diamine;
N4,N4-dimethyI-N2-(cis-4-{[(3,4,5-trimethoxybenzyl)amino]methyl}-cyclohexyl)pyrimidine-
2,4-diamine;
4-({[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexy!)-methyl]amino} methyl)-
2-iodo-6-methoxyphenol;
4-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-amino}methyl)-
2,6-dimethylphenoI;
N2-(cis-4-{[(5-bromo-2,4-diraethoxybenzyI)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;

186
N2-(cis-4-{[(5-bromo-2-methoxybenzyl)amino]methyi}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N"-[cis-4-({[4-(diethylamino)benzyl]amino}methyI)cyclohexyl]-N4,N4-dimethylpyrimidine-
2,4-diamine;
N2-[cis-4-({[(9-ethyl-9H-carbazoi-3-yl)methyl]amino}methyl)cyclohexyl]-N4,N4-
dimethyIpyrimidine-2,4-diamine;
N2-(cis-4-{[(4-isopropoxybenzyl)amino]methyl}cyC1-5hexyl)-N4,N4-dimethylpyrimidine-2,4-
diamine;
N"-(cis-4-{[(3,3-diphenylprop-2-en-l-yl)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
4-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-amino} methyl)-
2-ethoxyphenol;
N2-{cis-4-[({[4-(dimethylamino)-l-naphthyl]methyl}amino)raethyl]-cyC1-5hexyl}-N4,N4-
dimethylpyrimidine-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,6-trimethoxybenzyl)amino]methyl}-cyclohexyl)pyrimidine-
2,4-diamine;
N2-(cis-4-{[(5-bromo-2-ethoxybenzyl)amino]methyl}cyclohexyi)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(2,4-dimethoxy-3-methylbenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(2,5-diethoxybenzyI)amino]methyl}cyclohexyl)-N4,N4-dimethylpyrimidine-2,4-
diamine;
N2-(cis-4-{[(2,4-diethoxybenzyI)amino]methyI}cyclohexyl)-N4,N4-dimethylpyrimidine-2,4-
diamine;
N2-(cis-4-{[(3,5-dibromo-2-methoxybenzy!)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N4,N4-dimethyl-N"-(cis-4-{[(2,4,5-triethoxybenzyl)amino]methyl}-cyclohexyl)pyrimidine-
2,4-diamine;

187
N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-trimethoxybenzyI)amino]methyI}-cyclohexyI)pyrimidine-
2,4-diamine;
N"-[cis-4-({[2-tallyIoxy)benzyl]amino}methyl)cyclohexy]]-N4;N4-dimethyIpyrimidine-2,4-
diamine;
N4,N4-dimethyl-N2-[cis-4-({[(l-methyl-lH-indol-3-yl)methyl]amino}-methyl)cyclohexyI]-
pyrim idine-2,4-d iamine;
N"-[cis-4-({[(7-methoxy-l,3-benzodioxol-5-yI)methyI]amino}methyl)-cyclohexyl]-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(3-bromo-4,5-dimethoxybenzyi)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(4-methoxy-3-methylbenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrim id ine-2,4-d iamine;
N2-tcis-4-{[(2-bromo-4,5-dimethoxybenzyl)amino]methyI}cyC1-5hexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N^-(cis-4-{[(3,4-dimethoxybenzyl)amino]methyI}cyclohexyl)-N4,N4-dimethylpyrimidine-
2,4-diamine;
N2-(cis-4-{[(4-methoxy-2,5-dimethylbenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
3-[[4-({[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-methyl]amino}-
methy i)pheny 1] (methy l)am ino] propan en itri le;
N2-{cis-4-[({4-[(4-bromobenzyI)oxy]benzy]}amino)methyI]cyC1-5hexyl}-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(3,5-dibromo-2-ethoxybenzyl)amino]methyI}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-[4-(4-bromo-2-trifluoromethoxy-benzyl)amino-cyclohexyl]-N4,N4-dimethyl-pyrimidine-
2,4-diamine;
N2-{cis-4-[2-(4-bromo-2-trifluoromethoxy-phenyl)-ethylamino]-cyclohexyl}-N4,N4-
dimethyi-pyrimidine-2,4-diamine; and

1 oo
N"-{cis-4-[(4-bromo-2-trifluoromethoxy-benzyI)amino-methyl]-cyclohexyl}-N4,N4-
dimethyl-pyrimidine-2J4-diamine;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
ethyl 4,6-dichloro-3-{[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}-cyclohexyl)-
amino]methyI}-lH-indole-2-carboxylate;
N2-[cis-4-({[(4-methoxy-l-naphthyl)methyl]amino}methyl)cyclohexyl]-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-[cis-4-({[(2-methoxy-l-naphthyl)methyl]amino}methyl)cyclohexyl]-N4,N4-
dimethylpyrimidine-2,4-diamine;
4-bromo-2-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyC1-5hexyl)methyl]-
amino} methyl)-6-methoxyphenol;
N2-[cis-4-({[(5-bromo-lH-indoI-3-yl)methyl]amino}methyl)cyclohexyl]-N4,N4-
dimethylpyrimidine-2,4-diamine;
N4,N -dimethyl-N2-(cis-4-{[(2,3,4-trimethoxybenzyl)amino]methyl}-cyclohexyl)pyrimidine-
2,4-diamine;
N2-(cis-4-{[(3-ethoxy-4-methoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethyIpyrimidine-2,4-diamine;
N4,N4-dimethyl-N3-(cis-4-{[({3-[4-(trifluoromethyl)phenyl]-lH-pyrazol-4-yl}methyl)-
amino]methyI}cyclohexyI)pyrimidine-2,4-diamine;
4-( {[(cis-4- {[4-(dimethy lamino)pyrimidin-2-yl]amino} cyclohexyl)methyl]-amino} methy 1)-
2-iodo-6-methoxyphenol;
4-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)methyl]-amino}methyl)-
2,6-dimethylphenol;
N2-(cis-4-{[(5-bromo-2,4-dimethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(5-bromo-2-methoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-

189
dimethyIpyrimidine-2,4-diamine;
N2-[cis-4-({[(9-ethyl-9H-carbazol-3-yl)methyl]amino}methyl)cyC1-5hexy!]-N4,N4-
dimethyIpyrimidine-2,4-diamine;
N2-(cis-4-{[(3,3-dipheny]prop-2-en-l-yl)amino]methyl}cyclohexyl)-N4,N4-
d i methy I pyrim id ine-2,4-d iam i n e;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,6-trimethoxybenzyl)amino]methyI}-cyC1-5hexyl)pyrimidine-
2,4-diamine;
N2-(cis-4-{[(5-bromo-2-ethoxybenzyl)amino]methyl}cyclohexyI)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(2,4-dimethoxy-3-methyIbenzyl)amino]methyl}cycbhexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(2,5-diethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-dimethylpyrimidine-2?4-
diamine;
N2-(cis-4-{[(3,5-dibromo-2-methoxybenzyl)amino]methyl}cyC1-5hexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N4,N4-dimethyI-N2-(cis-4-{[(2,4,5-triethoxybenzyl)amino]methyl}-cyC1-5hexyl)pyrimidine-
2,4-diamine;
N2-[cis-4-({[2-(allyloxy)benzyl]amino}methyl)cyclohexyI]-N4,N4-dimethylpyrimidine-2,4-
diamine;
N2-[cis-4-({[(7-methoxy-I,3-benzodioxol-5-y!)methyl]amino}methyl)-cyclohexyl]-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(3-bromo-4,5-dimethoxybenzyl)amino]methyl}cyC1-5hexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N"-{cis-4-[2-(4-bromo-2-trifluoromethoxy-phenyl)-ethylamino]-cyclohexyl}-N4,N4-
dimethyl-pyrimidine-2,4-diamine; and
N2-{cis-4-[(4-bromo-2-trifluoromethoxy-benzyl)amino-methyl]-cyclohexyl}-N4,N4-
dimethy!-pyrimidine-2,4-diamine;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.

190
In some embodiments of the present invention, Ri is selected from the group consisting of:
(i) C1-5 alky], and
C1-5 alky I substituted by substituent(s) independently selected from the group
consisting of:
•oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•C1-5 alkylcarbonyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by nitro,
'carbocyclic aryloxy substituted by C1-5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by d.5 alkyl,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylamino,
•di-Cj.5 alkylamino,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•di-carbocyclic arylamino substituted by halogen,
"carbocyclic arylcarbonylamino,
*C1-5 alkoxycarbonylamino,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by substituent(s) independently selected from the
group consisting of:
"carbocyclic aryl, and

191
••carbocyclic aryl substituted by substituent(s) independently
selected from the group consisting of:
—halogen, and
"••C1-5 alkoxy,
•carbocyclic aryithio,
•heterocyclylthio,
•heterocyclylthio substituted by C1-5 alkyl,
•heterocyclylthio substituted by nitro,
•C3-6 cycloalkyl,
•C3-6 cycloalkenyl,
•carbocyclyl,
•carbocyciyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
"C|.s alkyl,
••Cj-5 alkoxy,
••C2-5 alkenyl, and
••C2-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryi substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••nitro,
••C1-5 alkyl,

192
"Cj-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
•"OXO,
"•carbocyclic aryl, and
•••heterocyclyl,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by halogen,
"C1-5 alkoxy substituted by carbocyclic aryl,
"carbocyclic aryloxy,
"carbocyclic aryl, and
••heterocyclyl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5 alkyl,
"C1-5 alkyl substituted by carbocyclic aryl,
•*C1-5 alkoxy,
"Cj-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryi, and
••carbocyclic aryl substituted by halogen,
(ii) C2-5 alkenyl, and
C2-g alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
"nitro,

193
(iii) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkyl,
•C1-5 aikyl substituted by substituent(s) independently selected from the
group consisting of:
'•oxo, and
••carbocyclic aryl, and
•carbocyclic aryl,
(iv) carbocyclyl,
(v) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
'Cj-5 alkyl,
•C|_5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
"0X0,
••carbocyclic aryloxy,
"carbocyclic aryl, and
••carbocyclic ary! substituted by C1-5 alkyl,
•C1-5 alkoxy,
•C|.5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:

194
••halogen, and
••carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-Ci-s alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C^ alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•amino,
•mono-Ci-s alkylamino,
•di-C1-5 alkylamino,
■C2.5 alkynylcarbonylamino,
•C2-5 alkynylcarbonylamino substituted by carbocyclic aryi,
•(carbocyclic aryl)NHC(O)NH,
•(carbocyclic aryl)NHC(O)NH substituted by C1-5 alkoxy,
•(carbocyclic aryl)NHC(O)NH substituted by haloganated C1-5 alkoxy,
'C1-5 alkylthio,
•C1-5 alkylthio substituted by halogen,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by cyano,
•mono-C1-5 alkylaminosulfonyl,
*di-C1-5 alkylaminosulfonyl, and
•carbocyclic aryl,
•carbocyclic aryl substituted by halogen,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•"C1-5 alkyl,

195
••carbocyclic aryl, and
••halogenated carbocyclic aryl,
(vi) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
•Ci-s alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
"C,_5 alkylthio,
"C1-5 alkylthio substituted by carbocyclic aryl,
••C[-5 alkylthio substituted by halogenated carbocyclic aryl,
"carbocyclic aryl,
•"carbocyclic aryl substituted by halogen, and
••heterocyclyl,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C1-5 alkyl,
•C1-5 alkylthio,
•C2-5 atkenylthio,
•carbocyclic arylthio,
•C],5 alkylsulfonyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by C1-5 alkyl,
•carbocyclic aryl,

196
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
"nitro, and
••C1-5 alkyl,
•heterocyclyl;
L is Formula (VII);
Y is -C(O)-;
wherein carbocyclic aryl is phenyl, naphthyl, or anthranyi;
carbocyclyl is 1,2,3,4-tetrahydronaphthyl, 1-oxo-indanyl,
9-oxo-9#-fluorenyI, or indenyl;
heterocyclyl is 1,2,3-triazoIyl, 1/f-indolyl, li/-pyrrolyl,
2,3-dihydro-l-oxo-isoindolyI52,3-dihydro-benzofuryI, 2,4-dihydro-3-oxo-pyrazolyl,
2//-benzopyranyI, 2-oxo-benzopyranyl, 4-oxo-l ,5,6,7-tetrahydro-indolyl,
9//-xanthenyl, benzo[l,3]dioxolyl, benzo[2,l,3]oxadiazolyl,
benzo[l,2,5]oxadiazolyl, benzo[b]thienyl, benzofuryl, benzothiazolyl, furyl,
imidazolyl, isoxazolyl, morpholino, pyrazolyl, pyridyl, pyrimidyl, quinolyl,
quinoxalyl, thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R2 is hydrogen, trifluoromethyl, methoxy,
methylamino, dimethylamino, ethylamino, ethylmethylamino, or hydroxylethylmethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-; or a pharmaceutically
acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Rx is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substiruent(s) independently selected from the group
consisting of:

197
•0X0,
•carbocyclic aryloxy.,
•carbocyclic aryloxy substituted by halogen,
"carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-C1-5 alkyiaminocarbonyl,
•di-C1-5 alkyiaminocarbonyl,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-carbocyclic arylamtno,
•di-carbocyclic arylamino,
"mono-carbocyclic arylamino substituted by halogen,
•di-carbocyclic arylamino substituted by halogen,
•carbocyclic arylcarbonylamino,
•C1-5 alkylthio,
•C3-6 cycloalkyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C,_5 alkyl,
••C2-5 alkenyl, and
••C2-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••earbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:

198
••halogen,
••hydroxy,
••nitro,
"C1-5 alkyl,
"C1-5 alkyl substituted by substituent(s) independently selected from
the group consisting of:
—oxo,
"•carbocyclic aryl, and
•••heterocyclyl,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by halogen,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••d.5 alkyl,
••carbocyclic aryl, and
"carbocyclic aryl substituted by halogen,
(ii) C2-5 alkenyl, and
C2-5 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
••nitro,
(iii) carbocyclyl,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the

199
group consisting of:
•halogen,
•hydroxy,
•nitro,
•C 1.5 alky!,
•Ci-s alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••oxo, and
•"carbocyclic aryl,
•C1-5 alkoxy,
*C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••carbocyclic aryl,
•carbocyclic aryloxy,
"carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
"mono-C]-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•C2-5 alkynylcarbonylamino,
•C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,
•mono-C1-5 alkylaminosulfonyl, and
•di-Cj.5 alkylaminosulfonyl,
(v) heterocyclyl, and

200
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
■C1-5 alky],
•Cj-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
«C1-5 alkylthio,
"C1-5 alkylthio substituted by carbocyclic aryl,
••C1-5 alkylthio substituted by halogenated carbocyclic aryl,
••carbocyclic aryl,
""carbocyclic aryl substituted by halogen, and
••heterocyclyl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C1-5 alkyl,
•C1-5 alkylthio,
•C1-5 alkylsulfonyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by C|_5 alkyl,
•carbocyclic aryl,
•carbocyclic ary! substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
"C1-5 alkyl,
•heterocyclyl;
wherein carbocyclic aryl is phenyl or naphthyl;

201
carbocyclyl is 1-oxo-indanyl, 9-oxo-9#-fluorenyl, or indenyl;
heterocyclyl is 1,2,3-triazolyI, 1/f-indolyl, l#-pyrrolyl,
2,3-dihydro-benzofuryl, 2i/-benzopyranyl, 9//-xanthenyl, benzo[2,l,3]oxadiazolyl,
benzo[l,2,5]oxadiazolyl, benzo[b]thienyl, furyl, isoxazolyl, morpholino, pyrazolyl,
pyridyl, quinolyl, quinoxalyl, thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R! is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•oxo,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by CV5 alkoxy,
•mono-C1-5 alkylamino,
*di-Cj_5 alkylamino,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•di-carbocyclic arylamino substituted by halogen,
•C,_5alkylthio,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••C,_s alkyl,

202
"C1-5 alkoxy, and
••C1-5 alkoxy substituted by halogen,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
"C1-5 alkyl,
••carbocyclic aryl, and
••carbocyclic aryl substituted by halogen,
(ii) C2-5 alkenyl, and
C7.5 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by nitro,
(iii) carbocyclyl,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by halogen,
•C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclic aryloxy,
'carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-C1-5 alky lam inocarbonyl,

203
•di-C1-5 alky lam inocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•mono-C1-5 alkylaminosulfonyl, and
•di-C1-5 alkylaminosulfonyl,
(v) heterocyclyl., and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
• nitro,
•C,_5 alkyl,
•C1-5 alky! substituted by substituent(s) independently selected from the
group consisting of:
"Cj.5 alkylthio,
"C1-5 alkylthio substituted by carbocyclic aryl, and
"Cj-5 aikylthio substituted by halogenated carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C|.5 alkyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by halogen,
•carbocyclic aryl substituted by nitro, and
•heterocyclyl;
wherein carbocyclic aryl is phenyl or naphthyl;
carbocyclyl is 1 -oxo-indanyl;
heterocyclyl is 1,2,3-triazolyl, \H-'mdo\y\, l//-pyrrolyl,
2,3-dihydro-benzofuryl, 9//-xanthenyI, benzo[2,l,3]oxadiazolyl,
benzo[l,2,5]oxadiazoiyl, benzo[b]thienyl, ftiryl, isoxazoiyl, pyridyl, quinoxalyl,

204
thiazolyl, or thienyi; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I)
wherein the compound is selected from the group consisting of:
N-(cis~4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-methoxybenzamide;
3-bromo-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-benzamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-2,l,3-benzoxadiazole-5-
carboxamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-benzamide;
4-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-benzamide;
4-chloro-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-3-
nitrobenzamide;
3,5-dichloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}-cyclohexyl)benzamide;
3,4-dichloro-N-(cis~4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidm-2-yl]amino}cyclohexyl)-2,2-diphenylacetamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3,4-difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-3,5-diftuorobenzamide;
N-(cis-4- {[4-(dimethy lamino)pyrimidin-2-yl]amino} cyclohexyl)-3-fluoro-5-
(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-4-methyl-3-
nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-phenoxybutanamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-3-methyIbenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidtn-2-yl]amino}cyclohexyl)-3-(trifluoromethoxy)-
benzamide;
4-bromo-N-(cis-4-{[4-(dimethyIamtno)pyrimidin-2-yl]amino}cyC1-5hexyl)-3-

205
methyl benzamide;
N-(cis-4-{[4~(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-3-iodobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2,5-dimethyl-3-furamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-4-
fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3,5-dimethoxybenzamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-3,5-bis(trifluoromethyl)-
benzamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-4-fluoro-3-
methy lbenzam i de;
2,5-dichloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyC1-5hexyl)thiophene-3-
carboxamide;
l-benzyl-3-tert-butyl-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}-cyclohexyI)-lH-
pyrazole-5-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(l-naphthyl)acetamide;
2-(4-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}-cyclohexyl)-
acetamide;
l-(4-chiorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)-
cyc lopentanec arboxam ide;
3-(2-chIoro-6-fluorophenyl)-N-(cis-4-{[4-(dimethy!amino)pyrimidin-2-yl]amino}-
cyclohexyl)-5-methylisoxazoIe-4-carboxamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-4-fluoro-3-
(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethy!amino)pyrimidin-2-yI]amino}cyclohexyl)-5-methyl-2-phenyl-2H-
1,2,3-triazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-y]]amino}cyclohexyl)-2-(4-methoxyphenoxy)-5-
nitrobenzamide;
N-(cts-4-{[4-(dimethylamino)pyrimidin-2-y]]amino}cyclohexyl)-2-phenoxyacetamide;

206
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-quinoxaline-2-
carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-3-(trifluoromethyl)-
benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(pentafluorophenoxy)-
acetamide;
2-(3-chiorophenoxy)-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
acetamide;
3-(2,6-dichIorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-5-
methylisoxazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-phenoxynicotinamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexy!)-2-(4-methylphenoxy)-
nicotinamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-4-[(dipropylamino)-
sulfonyl]benzamide;
2-(4-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-
methylpropanamide;
2-(2,3-dihydro-l-benzofliran-5-yl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)-l,3-thiazole-4-carboxamide;
3-tert-butyI-l-(2;4-dichIorobenzyl)-N-(cis-4-{[4-(dimethylarnino)pyrimidin-2-yl]amino}-
cyclohexyl)-lH-pyrazole-5-carboxamide;
6-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2H-chromene-3-
carboxamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyI)-2-(2-thienyl)-l,3-thiazoIe-
4-carboxamide;
5-(4-chloro-2-nitrophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
2-furamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyC1-5hexyI)-5-iodo-2-furamide;

207
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-5-(4-methyl-2-
nitrophenyI)-2-furamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyI)-5-nitrothiophene-2-
carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-methyl-4-
nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-y!]amino}cyC1-5hexyl)-3-methoxy-4-
nitrobenzamide;
l-benzyl-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-lH-indole-3-
carboxamide;
3-acetyl-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-benzamide;
5-bromo-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-y l]amino} cyclohexyl)-2-fliramide;
5-(4-chlorophenyl)"N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)-2-
furamide;
4,5-dibromo-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyI)thiophene-2-
carboxamide;
2-(3,5-di-tert-butyl-4-hydroxyphenyI)'N-(cis-4-{[4-(dimethylamino)-pyrimidin-2-
yljamino} cyclohexyl)acetamide;
N",N -dibenzoyI-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}-cyclohexyl)-
lysinamide;
3-(dimethylamino)-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}-cyclohexyl)-
benzamide;
4,5-dibromo-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}-cyclohexy])-2-furarnide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-2-(lH-indol-3-yl)-
acetamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyc]ohexyI)-2-(5-methyl-2-phenyl-l,3-
thiazol-4-y])acetamide;
N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexy l)-2-( 1 H-indol-3-yi)-4-oxo-4-

208
phenylbutanamide;
4-(4-bromophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)-2-(lH-
indoI-3-yl)-4-oxobutanamide;
3!5-dichIoro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyI)-2-[(3-
pheny lprop-2 -ynoy I)am i no] benzam id e;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-2-(l-methyl-lH-indolo-
yl)-4-(4-methylphenyl)-4-oxobutan amide;
N-(cts-4-{[4-(dimethylamino)pyrimidin-2-yl]amino} eye IohexyI)-2-methyl-l-(3-morpholin-
4-ylpropyl)-5-phenyl-lH-pyrroIe-3-carboxamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-4-(4-nitrophenyl)-
butanamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(2-phenyl-lH-indol-3-
y])acetamide;
N2-benzoyl-N5-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}-cyclohexyl)-N1,N1-
dipropylglutamamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-phenoxybenzamide;
3-benzoyl-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}-cyC1-5hexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-2-(etbyIthio)-2,2-
diphenylacetamide;
N-(cis-4-{[4-(dimethy!amino)pyrimidin-2-yI]amino}cyclohexyl)-N'-[(lR)-l-(l-
naphthyl)ethyl]phthalamide;
(2S)-2-(3-benzoylphenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
propanamide;
N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-N,N-bis[(lS)-l-
phenylethyl]phthalamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-{(lE)-5-fluoro-2-methyl-
1 -[4-(methylsulfinyl)benzylidene]-1 H-inden-3-y!} acetamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-2-[4-(2-thienylcarbonyl)-

209
phenyljpropan amide;
3-(benzyloxy)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyc]ohexyI)-4-
methoxybenzamide;
N-(cis-4-{[4-(dimethy!amino)pyrimidin-2-yl]amino}cyclohexyl)-2-methy]-l,5-diphenyl-lH-
pyrroIe-3-carboxamide;
I - {2-[(2-chloro-6-fiuorobenzyl)thio]ethyI} -N-(cis-4- {[4-(dimethy lamino)-pyrimidin-2-y 1]-
amino}cyclohexyl)-2-methyI-5-phenyI-IH-pyrroIe-3-carboxamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyI)-2-phenoxybenzamide;
N-(cis-4- {[4-(dimethylamino)pyrimidin-2-y Ijamino} cyclohexy l)-2-pheny lquinoline-4-
carboxamide;
2-[4-(4-chlorophenyl)-2-phenyl-l,3-thiazol-5-yl]-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino} cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-l-[(4-methylphenyl)-
suIfonyI]-lH-pyrrole-3-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-5-(3-nitrophenyl)-2-
furamide;
3-chloro-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-4-
(isopropylsulfonyl)-5-(methylthio)thiophene-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-3-iodo-4-
(isopropyIsu!fonyl)-5-(methylthio)thiophene-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-5-nitrothiophene-3-
carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-l-methyl-4-nitro-lH-
pyrrole-2-carboxam i de;
N-(cis-4-{[4-(dimethylaraino)pyrimidin-2-yI]amino}cyclohexyl)-4-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-3,5-dimethyl-4-
nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-mesityl-2-oxoacetamide;

210
3,5-di-tert-butyl-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}-cyC1-5hexyl)-4-
hydroxybenzamide;
4-chIoro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexy])-methy]]-
benzamide;
(2E)-N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyclohexyI)-methyl]-3-
phenylacrylamide;
4-chloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-y]]amino}cyclohexyl)-methy]]-3-
nitrobenzamide;
2-(4-chloropheny!)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)-
methy 1] acetam ide;
3,5-dichIoro-N-[(cis-4-{[4-(dimethy!amino)pyrimidin-2-yl]amino}-cyclohexyl)methy]]-
benzamide;
3,4-dichloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)methyl]-
benzamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)methyI]-2,2-
diphenylacetamide;
2,4-dichloro-N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}-cyclohexyl)methyl]-5-
fluorobenzamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin"2-yl]amino}cyclohexyl)methyl]-2-
ph enoxybutanam ide;
N-[(cis-4-{[4-fdimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)methyI]-2-
phenylbutanamide;
N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-(3-
methoxyphenyi)acetamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-(4-
m eth oxypheny l)ac etam ide;
N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyclohexyI)methyl]-3,5-
bis(trifluoromethyl)benzamide;

211
(2E)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-methyl]-3-(4-
nitropheny])acrylamide;
2-(2-bromophenyI)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)-
methyl] acetamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-(propyIthio)-
nicotinamide;
N-[(cis-4-{[4-(dimethyiamino)pyrimidin-2-yl]amino}cyclohexyI)methyI]-2-(l-naphthyI)-
acetamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-9-oxo-9H-
fluorene-4-carboxamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2,4,6-
trimethylbenzamide;
2,4,6-trichloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)methyl]-
benzamide;
(2E)-3-(2-chlorophenyI)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
methyl]acrylamide;
N-[(cis-4-{[4-(dimethy!amino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-(2,3,6-
trichlorophenyl)acetamide;
N-[(cis-4-{[4-(dimethyIarnino)pyrimidin-2-yl]amino}cyclohexyl)methy!]-2,3-
d iphenylpropanam i de;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-5-iodo-2-
fliramide;
(2E)-N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-methyl]-3-(3-
nitrophenyl)acrylamide;
N-[(cis-4-{[4-(dimethylamino)pynmidin-2-yl]amino}cyC1-5hexy])methyl]-3-oxoindane-l-
carboxamide;
2-benzyI-N-[(cis~4-{[4-(dimethylamino)pyrimidin-2-y!]amino}cyC1-5hexyl)-methyl]-
benzamide;

212
2,2-bis(4-chlorophenyl)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
methyl] acetamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-3-methyl-4-
nitrobenzamide;
N-[(cis-4-{[4-(dimethy]amino)pyrimidin-2-yl]amino}cyC1-5hexyl)methyl]-3-methoxy-4-
nitrobenzamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-[2-
(trifluoromethoxy)phenyl] acetamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-9H-xanthene-9-
carboxamide;
2-(l-benzothien-3-yl)-N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
methyl]acetamide;
N-[cis-4-(4-dimethyIamino-pyrimidin-2-ylamino)-cyclohexyl]-2-(4-fluoro-phenoxy)-
nicotinamide;
N-[cis-4-(4-dimethy!amino-pyrimidin-2-ylamino)-cyC1-5hexyl]-C-(ethyl-pheny!-amino)-
acetamide;
C-[cis-(4-chloro-phenyl)-ethyl-amino]-N-[4-(4-dimethylamino-pyrimidin-2-ylamino)-
cyclohexylj-acetamide;
2-(3,4-difluoro-phenyI)-N-[cis-4-(4-dimethylamino-pyrimidin-2-y]amino)-cyclohexyl]-
acetamide;
4-chloro-N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-3-fluoro-benzamide;
5-bromo-N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyC1-5hexyl]-nicotinamide;
3-chloro-4-fluoro-N-[cis-4-(4-methylamino-pyrimidin-2-ylamino)-cyclohexyI]-benzamide;
N-[cis-4-(4-dimethyiamino-pyrimidin-2-ylamino)-cyclohexy]]-4-fluoro-benzamide;
3-chloro-N-[cis-4-{4-dimethylamino-pyrimidin-2-ylamino)-cyclohexy]]-5-fluoro-benzamide;
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-3,4,5-trifluoro-benzamide;
N-[cis-4-(4-dimethylamino-pyrimidin-2-yIamino)-cyclohexyImethyl]-3,4-difluoro-
benzamide;

213
2-(3,4-dichloro-phenoxy)-N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-
acetamide;
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-2-(3-methoxy-phenoxy)-
acetamide; and
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-C-(ethyI-phenyl-amino)-
acetamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
3-bromo-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-benzamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-2,l,3-benzoxadiazole-5-
carboxamide;
3-chloro-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyC1-5hexyl)-benzamide;
4-chIoro-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyclohexyl)-3-
nitrobenzamide;
3,5-dichloro-N-(cis-4-{[4-(diroethylamino)pyrimidin-2-yl]amino}-cyclohexyl)benzamide;
3,4-dichIoro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}-cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3,4-difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-nitrobenzamide;
N-(cis-4- {[4-(dimethyIamino)pyrimidin-2-yl]amino} cyc]ohexyI)-3-(trifluoromethoxy)-
benzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-3-
methylbenzamide;
N-(cis-4-{[4-{dimethyIamino)pyrimidin-2-yl]amino}cyc]ohexyl)-3-iodobenzamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}eyc!ohexyl)-4-
fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3,5-dimethoxybenzamide;
N-(cis-4-{[4-(dimethyIamino)pyriniidin-2-yI]amino}cyclohexyl)-3,5-bis(trifluoromethyl)~

214
benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-4-fiuoro-3-
methylbenzamide;
2-(4-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyC1-5hexyl)-
acetamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-4-fluoro-3-
(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyclohexyl)-5-methyI-2-phenyl-2H-
1,2,3-triazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-2-(4-methoxyphenoxy)"5-
nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-quinoxaIine-2-
carboxamide;
2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]aniino}-cyC1-5hexyl)-
acetamide;
3-(2,6-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-5-
methylisoxazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(4-methylphenoxy)-
nicotinamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-4-[(dipropylamino)-
sulfonyljbenzamide;
2-(2,3-dihydro-I-benzoftiran-5-yI)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)-l,3-thiazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(2-thienyl)-l,3-thiazole-
4-carboxamide;
5-(4-chloro-2-nitrophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexy])-
2-furamide;
N-(cis-4-{[4-(dtmethylamino)pyrimidin-2-yl]amino}cyC1-5hexyI)-3-methoxy-4-

215
nitrobenzaraide;
5-bromo-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-2-furamide;
5-(4-chIorophenyl)-N-(cis-4-{[4~(dimethylamino)pyrimidin-2-yl]amino}-cyC1-5hexyl)-2-
furamide;
2-(3,5-di-tert-buty]-4-hydroxyphenyl)-N-(cis-4'{[4-(dimethylamino)-pyrimidin-2-yi]-
amino} cyclohexyi)acetamide;
4,5-dibromo-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}-cyC1-5hexyl)-2-furamide;
N-(cis-4- {[4-(dimethylamino)pyrim Jdin-2-yl]amino} cyclohexy l)-2-( 1 H-indoI-3-yl)-4-oxo4-
phenylbutanamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-2-(l-methyI-lH-indoI-3-
yl)-4-(4-methy!phenyl)-4-oxobutanamide;
N-(cts-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-t2-phenyI-lH-indoI-3-
yl)acetamide;
N-tcis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(ethylthio)-2,2-
diphenylacetamide;
N'-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyI)-N,N-bis[(lS)-l-
phenylethyl]phthalamide;
3-(benzyIoxy)-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} -cyclohexyl)-4-
methoxybenzamide;
N-(cis-4-{ [4-(dimethylamino)pyrimidin-2-yI]amino} cyc!ohexyl)-2-methyl-1,5-diphenyl-1H-
pyrrole-3 -carboxam ide;
I-{2-[(2-chloro-6-fluorobenzyl)thio]ethyI}-N-(cis-4-{[4-(dimethylamino)-pyrimidin-2-yl]-
amino}cyC1-5hexyl)-2-methyl-5-phenyl-lH-pyrrole-3-carboxamide;
2-[4-(4-chIorophenyI)-2-phenyI~l,3-thiazo]-5-y]]-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)acetamide;
N-(cis-4-{[4-{dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-5-nitrothiophene-3-
carboxamide;
N-(cis-4- {[4-(dimethylamino)pyrimidin-2-y IJamino} cyclohexyl)-1 -methyl-4-nitro-1H-

216
pyrrole-2-carboxamide;
3,5'di-tert-butyl-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}-cyclohexyl)-4-
hydroxybenzamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyI]-2,2-
diphenylacetamide;
N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyI)methyl]-2-
phenylbutanamide;
(2E)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-methyl]-3-(4-
nitrophenyl)acrylamide;
N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyI)methyl]-2-(l-naphthyI)-
acetamide;
N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-(2,3,6-
trichlorophenyl)acetamide;
(2E)-N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-methyl]-3-(3-
nitrophenyl)acrylamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)methyl]-3-oxoindane-l-
carboxamide;
2,2-bis(4-chlorophenyI)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyI)-
methyl] acetamide;
N-[(cis-4-{[4-(dimethylamJno)pyrimidin-2-yI]amino}cyclohexyI)methyl]-3-methyl-4-
nitrobenzamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-3-methoxy-4-
nitrobenzamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-[2-
(trifluoromethoxy)phenyl] acetamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)methyl]-9H-xanthene-9-
carboxamide;
2-(l-benzothien-3-yi)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-y]]amino}cyclohexyl)-

217
methyl ]acetamide;
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-2-(4-fluoro-phenoxy)-
nicotin amide;
N-[cis-4-(4-dimethyIamino-pyrimidin-2-ylamino)-cyclohexyl]-C-(ethyI-pheny]-amino)-
acetamide;
C-[cis-{4-chIoro-phenyl)-ethyl-amino]-N-[4-(4-dimethylamino-pyrimidin-2-yIamino)-
cyclohexyl]-acetamide;
4-chloro-N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyI]-3-fluoro-benzamide;
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-3,4,5-trifluoro-benzamide;
2-(3,4-dichIoro-phenoxy)-N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-
acetamide;
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyC1-5hexyl]-2-(3-methoxy-phenoxy)-
acetamide; and
N-[cis-4-(4-dimethyIamino-pyrimidin-2-yIamino)-cyclohexyl]-C-(ethyI-phenyl-amino)-
acetamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•C1-5 alkoxy carbonyl,
•CN5 alkylthio,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
"C\_5 alky!, and
"C2-5 alkenyl,

218
(ii) C3-6 cycloalkyl,
C3-6 cycloalkyl substituted by carbocyclic aryl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•cyano,
•nitro,
•Q.5 alkyl,
*C1-5 alkyl substituted by halogen,
•C1-5 alkoxy carbonyl,
•Cj.5 alkoxy,
•C3-6 cycloalkoxy,
•carbocyclic aryloxy,
■C1-5 alkylthio, and
•carbocyclic aryl,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen, and
•carbocyclic aryl;
L is Formula (VII);
Y is -C(O)NR5-;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is 2,3-dihydro-benzo[l,4]dioxinyl,
3,4-dihydro-2//-benzo[b][l,4]dioxepinyl, benzo[l,3]dioxolyl, furyl, or isoxazolyl;
and

219
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R? is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-: R5 is hydrogen; or a
pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R[ is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by carbocyclic aryl,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
■C1-5 alkyl substituted by halogen,
•C1-5 alkoxy, and
•C3^ cycloalkoxy,
(iii) heterocyclyl, and
heterocyclyl substituted by C1-5 alkyl, and
heterocyclyl substituted by carbocyclic aryl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is isoxazolyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-N'-mesitylurea;
N-(cis-4-{[4-(dimethyiamino)pyrimidin-2-yl]amino}cyclohexyI)-N'-(2,4,6-trichlorophenyI)-

220
urea;
N-(cis-4-{[4-(dimethylamino)pyrirnidin-2-yl]amino}cyC1-5hexyl)-N'-(2,4,6-tnbrornopheny])-
urea;
N-(2,4-dibromo-6-fIuorophenyI)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}-
cyclohexyl)urea;
N-(cis-4-{[4-(dimethyiamino)pyrimidin-2-yI]amino}cyclohexyl)-N'-(diphenylmethyl)urea;
N-(4-bromo-2,6-dimethylphenyI)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)urea;
N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexy l)-N'-[ 1 -(1 -naphthyl)ethyl]-
urea;
N-tcis-4-{[4-(dimethyiamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-Nl-(3,4,5-
tri methoxypheny l)urea;
N-(4-chIoro-2-methy lphenyl)-N'-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} -
cyclohexyl)urea;
N-(5-chloro-2;4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-pyrimidin-2-yl]amino}-
cyclohexy l)urea;
N-(4-bromo-2-methylphenyI)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)urea;
N-(2J6-dibromo-4-isopropylphenyI)-N'-(cis-4-{[4-(dimethylamino)-pyrimidin-2-yl]amino}-
cyclohexyl)urea;
N-[3-(cyclopentyIoxy)-4-methoxyphenyI]-N'-(cis-4-{[4-(dimethylamino)-pyrimidin-2-yl]-
amino} cyclohexyl)urea;
N-[(cis-4-{[4-(dimethylamino)pyrimidm-2-yl]amino}cyclohexyl)methyI]-N'-(2,6-
dimethy]phenyt)urea;
N-(2,4-difluorophenyI)-Nt-[(cis-4-{[4-(dimethy]amino)pyrimidin-2-yl]amino} cyclohexy I)-
methyl]urea;
N-[(cis-4-{[4-(di(nethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-N'-(2-ethyl-6-
methylphenyl)urea;

221
N-[(cis-4-{[4-{dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)methy]]-N'-(4-
fluorophenyl)urea;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexy])methyl]-N'-mesityIurea;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)methyl]-N'-(2,4,6-
trichlorophenyl)urea;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)methyl]-N'-(2,4,6-
trib rom opheny l)urea;
N-(2,4-dibromo-6-fIuoropheny])-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)methyl]urea;
N-(2,6-diethylphenyI)-N'-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
methyl]urea;
N-[2-chloro-6-(trifluoromethyl)phenyl]-N'-[(cis-4-{[4-(dimethyIamino)-pyrimidin-2-yl]-
amino}cyclohexyl)methyl]urea;
N-(2-chloro-6-methylphenyl)-Nt-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)methyl]urea;
N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-yI]amino} cyclohexyl)methyl]-N'-(2-ethyl-6-
isopropylphenyl)urea;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-N'-(2-isopropyl-6-
methylphenyl)urea;
N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-y Ijamino} cyclohexy l)methyl]-N'-(2-methy 1-3-
nitrophenyl)urea;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyI)methyl]-N'-(2-
propylphenyl)urea;
N-(2-tert-butyl-6-methylphenyI)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)methyl]urea;
N-(2-tert-butylphenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
methyl] urea;
N-(3-chloro-2-methylphenyI)-Nt-[(ciS"4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-

222
eye lohexyl) methyl] urea;
N-(4-bromo-2,6-difluorophenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
eye lohexy I)methy 1] urea;
N-[4-chloro-2-(trifluoromethyi)phenyI]-N'-[(cis-4-{[4-(dimethylamino)-pyrimidin-2-yl]-
amino}cyclohexyl)methyl]urea;
N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyI)methyl]-N'-
(diphenylmethyl)urea;
N-(4-bromo-2,6-dimethyIphenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
eye lohexyl)methyl]urea;
N-[(cis-4-{[4-(dimethyiamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-N'-(3-methyl-5-
phenylisoxazol-4-yl)urea;
N-(3,5-dichIorophenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]-amino}cyC1-5hexyl)-
methyl] urea;
N-(2,3-dichlorophenyI)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]-amino}cyclohexyl)-
methyl]urea;
N-(2,6-diisopropylphenyI)-N'-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]-amino}-
cyclohexyl)methyl]urea;
N-E(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyc lohexy l)methyl]-N'-(2,3-dimethyl-
6-nitrophenyl)urea;
N-(2,6-dibromo-4-fluorophenyI)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)methyl]urea;
N-(2,6-dichlorophenyl)-N'-[(cis^-{[4-(dimethylamino)pyrimidin-2-yl]-amino}cyclohexyl)-
methyl]urea;
N-[(cis-4-{[4-(dimethylamino)pynmidin-2-yl]amino}cyclohexyl)methyl]-N'-(2-methoxy-5-
methylphenyl)urea;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-N'-(2-methyl-6-
nitrophenyl)urea;
N-(3,4-difluorophenyl)-Nt-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]-amino}cyC1-5hexyI)-

223
methyl] urea;
N-(3,5-difIuorophenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]-amino}cyC1-5hexyI)-
methyl] urea; and
N-(3-chloro-4-fluorophenyl)-N'-[(cis-4-{[4-(dimethy]amino)pyrimidin-2-yI]amino}-
eye lohexyl)methyl] urea;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R[ is selected from the group consisting of:
(i) C]_s alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen, and
••C]-5 alkoxy,
(ii) carbocyclyl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•cyano,
•nitro,
•C1-5 alkyl,
*C1-5 alkyt substituted by halogen,
"C1-5 alkoxy carbony!,
•C1-5 alkoxy,
•Q-5 alkoxy substituted by halogen,
•mono-C1-5 alkylamino,

224
•di-C1-5 alkylamino, and
•carbocyclic aryl,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•C,.s alkyl,
•Cjo alkoxy carbonyl, and
•carbocyclic aryl;
L is Formula (VII);
Y is -C(S)NR5-;
wherein carbocyclic aryl is phenyl or naphthyl;
carbocyclyl is bicyclo[2.2.1]heptyl;
heterocyclyl is 2,3-dihydro-benzo[l,4]dioxinyl, benzo[l,3]dioxolyl,
isoxazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutical ly acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R2 is methylamino, or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-; R5 is hydrogen; or a
pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Rj is selected from the group consisting of:
carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•cyano,
•C1-5 alkyl,
"C1-5 alkoxy,
•mono-C1-5 alkylamino, and

225
•di-C1-5 aikylamino;
wherein carbocyclic aryl is phenyl or naphthyi; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (1) wherein the
compound is selected from the group consisting of:
N-(4-cyanophenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}-cyclohexyl)-
thiourea;
N-(2,4-dimethoxyphenyl)-N'- cyc I ohexyl)th iourea;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-N'-(3,4,5-
trimethoxyphenyl)thiourea;
N-(354-dimethoxyphenyl)-Nf-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]-amino}-
cyclohexyl)thiourea;
N-[4-(dimethylamino)-l-naphthyI]-N'-(cis-4-{[4-(dimethylamino)-pyrimidin-2-yl]amino}-
cyclohexyl)th iourea;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-N'-(2,4,6-tribromophenyl)-
th iourea;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2'yl]amino}cyclohexyl)-N'-mesityIthiourea;
N-(4-bromo-2,6-dimethyIphenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)thiourea;
N-(5-chloro-2,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-pyrimidin-2-yl]amino}-
cy c lohexy I)th iourea;
N-(2,4-dibromo-6-fluorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}-
cyclohexyl)thiourea; and
N-(2,4-dichloro-6-methylphenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}-
cyclohexyl)thiourea;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.

226
In some embodiments of the present invention, Ri is selected from the group consisting of:
(i) Ci_8 alkyl, and
Ci-s alkyl substituted by substituent(s) independently selected from the group
consisting of:
•halogen,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclyl,
•carbocyclic aryl,
"carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
—nitro, and
"C1-5 alkoxy,
(ii) C2-5 alkenyl,
(iii) carbocyclyl,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen, and
•C1-5 alkoxy;
L is Formula (VII);
Y is -C(0)O;
wherein carbocyclic aryl is phenyl or naphthyl;
carbocyclyl is 9i/-fluorenyl or menthyl; and
halogen is fluoro, chloro, bromo, or iodo;

227
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-; or a pharmaceutically
acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Q is Formula (IV); p is 1 or 2;
Ri is selected from the group consisting of:
(i) C1-16 alkyl, and
Ci_ie alkyl substituted by substituent(s) independently selected from the
group consisting of:
•hydroxy,
•oxo,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
"C,_5 alkyl,
••C1-5 alkyl substituted by halogen, and
"C1-5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
"C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by substituent(s) independently
selected from the group consisting of:
••halogen,

228
"C1-5 alkoxy, and
»C[.5 alkyl,
•carbocyclic arylsulfmyl,
•carbocyclic arylsulfmyl substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
"C]o alkyl, and
"C1-5 alkyl substituted by halogen,
•carbocyclic arylsulfonyl,
"carbocyclic arylsulfonyl substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
"C1-5 alkyl, and
••C1-5 alky! substituted by halogen,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
—halogen,
••nitro,
•*C1-5 alkylcarbonylamino,
"C3-6 cycloalkylcarbonylamino,
••C,.g alkyl,
••C1-5 alkyl substituted by halogen,
"C1-5 alkoxy, and
"C1-5 alkoxy substituted by halogen, and
•heterocycly],
(ii) C3.12 cycloalkyl, and
C3-12 cycloalkyl substituted by substituent(s) independently selected from the

229
group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by substitutent(s) independently selected from
the group consisting of:
•• C1-5 alkoxy,
••halogen,
••C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•cyano,
•nitro,
•C1-50 alkyl,
•Ci-io alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
"hydroxy,
•Ci_9 alkoxy,
•C1-9 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••carbocyclic aryl,
•carboxy,
•C]o alkoxycarbonyl,
•di-C1-5 alkylamino,
*Ci_s alkylcarbonylamino,

230
*Ca-6 cycloalkylcarbonylamino,
•Cj.5 alkylthio,
•C1-5 alkylsulfinyl,
*C1-5 alkylsulfonyi,
•carbocyclic aryl,
(iv) heterocyclyl., and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•ammo,
•C1-5 alky],
•C1-5 afkyl substituted by halogen,
•C1-5 alkoxy,
"carbocyclic aryloxy,
•carbocyelic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
"C1-5 alkyl,
"C1-5 alky! substituted by halogen, and
"C1-5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by halogen,
•heterocyclyl sulfonyl,
• heterocyclyl sulfonyl substituted by C1-5 alkyl,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•C1-5 alkylthio,

231
*C]-5 alkylsulfmyl,
'carbocyclic arylsulfinyl,
•carbocyclic arylsulfinyl substituted by halogen,
•carbocyclic arylsuifonyl,
•carbocyclic arylsulfonyl substituted by substituents(s) independently
selected from the group consisting of:
••halogen,
"C1-5 alkoxy,
••C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
R2 is selected from the group consisting of:
amino, C1-5 alkyl, C\.5 alkoxy, -N(R2a)(R2b), wherein R2a is hydrogen or C1-5 alkyl and
R2b is C1-5 alkyl or C3-6 cycloalkyl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is 3,4-dihydro-l//-isoquinolinyl, benzo[l,3]dioxolyl, furyl,
isoxazolyl, oxazolyl, pyrazolyl, pyrazinyl, pyridyl, pyrimtdyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Ri is selected from the group consisting of:
(i) C1-16 alkyl, and
C]-i6 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•oxo,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
"Ci-s alky!,

232
"C1-5 alkyl substituted by halogen, and
"C1-5 alkoxy, and
••C1-5 alkoxy substituted by halogen,
(ii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic arylsulfinyl, and
•carbocyclic arylsulfinyl substituted by halogen,
L is Formula (VII);
Y is a single bond or -CH2-;
R2 is -N(R2a)(R2b), wherein R2a is C1-5 alkyl and R2b is C1-5 alkyl;
carbocyclic aryi is phenyl;
heterocyclyl is pyrazinyl; and
halogen is fluoro, chloro, or bromo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R! is selected from the group consisting of:
(i) C1-16 alkyl, and
C1-16 alkyl substituted by substituent(s) independently selected from the
group consisting of:
'carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen, and
••C 1.5 alkoxy,
(ii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic arylsulfinyl, and

233
•carbocyclic arylsulfinyl substituted by halogen,
R2 is -N(R2a)(R-2b)> wherein R2a is C1-5 alkyl and R2b is C1-5 alkyl;
carbocyclic aryl is phenyl;
heterocyclyl is pyrazinyl; and
halogen is fluoro or bromo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R] is selected from the group consisting of:
heterocyclyl, and
heterocyclyl substituted by substiruent(s) independently selected from the
group consisting of:
•carbocyclic arylsulfinyl, and
'carbocyclic arylsulfinyl substituted by halogen,
R2 is -N(R2a)(R2b), wherein R2a is C1-5 alkyl and R2t, is C1-5 alkyl;
carbocyclic aryl is phenyl;
heterocyclyl is pyrazinyl; and
halogen is fluoro;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, p is 1 and T is C1-5 alkyl; R3 and R4 are both
hydrogen; A and B are both single bonds: or a pharmaceutically acceptable salt, hydrate, or solvate
thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
N"-{cis-4-[(3,5-dimethoxybenzyl)amino]cyclohexyl}-N4,N4,5-trimethylpyrimidine-
2,4-diamine;
N"-{cis-4-[(3-bromobenzyI)amino]cyclohexyl}-N4,N4,5,6-tetramethylpyrimidine-2,
4-diamine;
N2-{cis-4-[(3,4-difluorobenzyl)amino]cyclohexyl}-N4,N4,5,6-tetramethylpyrimidine
-2,4-diamine; and

234
N2-[cis-4-({6-[(3,4-difluorophenyl)sulfinyl]pyrazin-2-y]}amino)cyC1-5hexyI]-N4,N4,5
-trimethyipyrimidine-2,4-diamine;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is:
N2-[cis-4-({6-[(3,4-difluorophenyl)sulfinyl]pyrazin-2-yI}amino)cyclohexyl]-N4,N4,5
-trimethyIpyrimidine-2,4-diamine;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R] is selected from the group consisting of:
(i) C]_i6 alkyl, and
C1-16 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•hydroxy,
'carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••C1-5 alkyl,
"C1-5 alkyl substituted by halogen, and
"Cj_5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
"C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
"inono-carbocyclic arylamino,
*mono-carbocyclic arylamino substituted by substituent(s) independently

235
selected from the group consisting of:
••halogen,
••C] 5 alkoxy, and
"C1-5 alkyl,
•carbocyclic arylsulfinyl,
•carbocyclic arylsulfinyl substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
•carbocyclic aryl,
■carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl,
'•Cj_5 alkyl substituted by halogen, and
"C1-5 alkoxy,
(ii) C3.12 cycloalkyl, and
C3-12 cycloalkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl, and

236
•carbocyclic aryl substituted by substitutent(s) independently selected from
the group consisting of:
•• C1-5 alkoxy,
••halogen,
••C1-5 alkyl, and
•*C1-5 alkyl substituted by halogen,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•cyano,
•nitro,
•Ci-io alkyl,
•Cj-io alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••hydroxy,
•C1-9 alkoxy,
•Ci_9 alkoxy substituted by halogen,
•carboxy,
•C1-5 alkoxycarbonyl,
•di-C1-5 alkylamino,
•C1-5 alkyIcarbonylamino,
•C3-6 eye loalky Icarbony lam ino,
"C1-5 alkylsulfonyl, and
•carbocyclic aryl,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the

237
group consisting of:
•halogen,
•hydroxy,
•amino,
•d-salky],
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
"halogen,
••C,.s alkyl,
•*C1-5 alkyl substituted by halogen, and
"C1-5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by halogen,
•heterocyclyl sulfonyl,
• heterocyclyl sulfonyl substituted by C1-5 alkyl,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•C1-5 alkylthio,
•C1-5 alkylsulfinyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by substituents(s) independently
selected from the group consisting of:
••halogen,
••C1-5 alkoxy,
••C1-5 alkyl, and

238
••C1-5 alkyl substituted by halogen,
L is Formula (VII);
Y is -C(O)-;
R2 is selected from the group consisting of:
amino, C|_5 alkyl, C1-5 alkoxy, -NtR2a)tR2b), wherein R2a is hydrogen or C1-5 alkyl and
R2b is C1-5 alkyl or C3^ cyC1-5alky];
wherein carbocyclic aryl is phenyl;
heterocyclyl is benzo[l,3]dioxolyl, furyl, isoxazolyl, oxazolyl, pyrazolyl,
pyrazinyl, pyridyl, pyrimidyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R] is selected from the group consisting of:
(i) C1-16 alkyl, and
C1-16 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•hydroxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••C1-5 alkyl,
"C1-5 alkyl substituted by halogen, and
"C1-5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by halogen,
•mono-carbocyclic arylamino,
"mono-carbocyclic arylamino substituted by substituent(s) independently
selected from the group consisting of:

239
••halogen,
"C1-5 alkoxy, and
"C1-5a!kyl,
•carbocyclic arylsuJfinyl,
•carbocyclic arylsulfmyl substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
"C1-5 alkyl, and
*-C1-5 alkyl substituted by halogen,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by substituent(s) independently
selected from the group consisting of:
"C]o alkyl, and
*"C1-5 alkyl substituted by halogen,
•carbocyclic aryl,
'carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••Ci-s alkyl, and
"C1-5 alkyl substituted by halogen,
(ii) C3.12 cycloalkyl, and
C3-12 cycloalkyl substituted by substituent(s) independently selected from the
group consisting of:
"carbocyclic aryl, and
•carbocyclic aryl substituted by substitutent(s) independently selected from
the group consisting of:
•" Cj-5 alkoxy,
••halogen,

240
"C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•cyano,
•nitro,
•CLIO alkyl,
*C]_io alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••hydroxy,
•C1-9 alkoxy.,
•C1.9 alkoxy substituted by halogen,
•carboxy,
•C1-5 alkoxycarbonyl, and
•C1-5 alkylsulfonyl,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C,-5 alkyi,
•C1-5 alky! substituted by halogen,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:

241
"halogen,
"Q-5 alkyl,
••C1-5 alkyl substituted by halogen, and
"C1-5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by halogen,
•heterocyclyl sulfonyl,
• heterocyclyl sulfonyl substituted by C1-5 alkyl,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•C1-5 alkylthio,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by substituents(s) independently
selected from the group consisting of:
••halogen,
"Cs_5 alkyl, and
••Cj_5 alkyl substituted by halogen,
R? is selected from the group consisting of:
C1-5 alkoxy, -N(R2a)(R2b), wherein R2a is hydrogen or C1-5 aikyl and R2b is C1-5 alkyl;
wherein carbocyclic aryl is phenyl;
heterocyclyl is benzo[l,3]dioxolyl, furyl, isoxazolyl, oxazolyl, pyrazolyl,
pyridyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Ri is selected from the group consisting of:
(i) C1-16 alkyl, and
C1-16 alkyl substituted by substituent(s) independently selected from the
group consisting of:

242
•hydroxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
"C1-5 alkyl,
"C1-5 alkyl substituted by halogen, and
•*C|_5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
••C1-5 alkoxy, and
••C1-5 alky],
•carbocyclic arylsulfinyl,
'carbocyclic arylsulfinyl substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
"C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
"carbocyclic aryl,
"carbocyclic aryl substituted by substituent(s) independently selected from

243
the group consisting of:
••halogen,
"C1-5 alkyl, and
••C1-5 alky] substituted by halogen,
(ii) C3.1? cycloalkyl, and
C3-12 cycloalkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by substitutent(s) independently selected from
the group consisting of:
••C1-5 alkoxy,
••halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•cyano,
•nitro,
•C1-50 alkyl,
•Ci_io alkyl substituted by halogen,
•C1-9 alkoxy, and
•Cj_9 alkoxy substituted by halogen,
(iv) heterocyctyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,

244
•d-s alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
"C,_5 alkyl,
•"C1-5 alkyl substituted by halogen, and
"C\_5 alkoxy,
•C1-5 alkylthio,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by halogen,
R? is selected from the group consisting of:
-N(R2a)(R-2bX wherein R2a is hydrogen or C1-5 alkyl and R2b is C1-5 alkyl;
wherein carbocyclic aryl is phenyl;
heterocyclyl is benzo[l,3]dioxolyl, ftiryl, pyrazolyl, pyridyl, or thienyl; and
halogen is fluoro, chioro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, p is 1 and T is C1-5 alkyl; R3 and R4 are both
hydrogen; A is a single bond and B is a single bond or -CH2-; or a pharmaceutically acceptable salt,
hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
N-[(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyI)methyI]-3,5-
bis(trifluoromethyl)benzamide;
N-[(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yI]amino}cyclohexyl)methyl]-3,5-
bis(trifluoromethyl)benzamtde;

245
N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyC1-5hexyi)methyl]-3,4-
difluorobenzam ide;
3,5-dichloro-N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-
methyl] benzamide;
N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyI)methyl]-3,4-
difluorobenzamide;
N-[(cis-4-{[4-(dimethy!amino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)methyl]-3,5-
dimethoxybenzamide;
N-[(cis-4-{[4-(dimethylamino)-5-methy]pyrimidin-2-yl]amino}cyclohexyl)methyl]-3-fluoro-
4-methylbenzamide;
N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)methyl]-3-
(trifluoromethyl)benzamide;
N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)methyI]-3-
(trifluoromethoxy)benzamide;
4-bromo-N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-
methyl]-3-methylbenzam ide;
N-[(cis-4-{[4-(dimethylamino)-5-methyJpyrimidin-2-yl]amino}cyclohexyl)methyl]-3-fluoro-
4-(trifluoromethyl)benzamide;
3,5-dichIoro-N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-
methyl]benzamide;
3,4-dichloro-N-[(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-
methyl]benzamide;
4-chloro-N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-
methyl]benzamide;
4-chloro-N-[(cis-4-{[4-(dimethylamino)-6-methy!pyrimidin-2-yl]amino}cyclohexyl)-
methyl]benzamide;
N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}methyl)cyclohexyI]-3,5-
dimethoxvbenzamide;

246
4-bromo-N-[cis-4-({[4-(dimethylamino)-5-methy]pyrimidin-2-yi]amino}methyI)-
cyclohexyljbenzamide;
4-bromo-N-[cis-4-({[4-(dimethy]amino)-5-methylpyrimidin-2-yI]amino}methyl)-
cyclohexylJ-3-methyIbenzamide;
3,5-dichloro-N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}methy!)-
cyclohexyljbenzamide;
3,4-dichIoro-N-[cis-4-({[4-(dimethyiamino)-5-methylpyrimidin-2-yl]amino}methyl)-
cyclohexyl]benzamide;
N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}methyI)cyclohexyl]-3,5-
bis(trifluoromethyl)benzamide;
N-[cis-4-({[4-(dimethyiamino)-6-methylpyrimidin-2-yl]amino}methyI)cyclohexyl]-3,4-
d i fluorobenzam ide;
4-bromo-N-[cis-4-({[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}methyl)-
eye 1 ohexy Ijbenzam ide;
4-bromo-N-[cis-4-({[4-(dimethylamino)-6-methy]pyrimidin-2-yI]amino}methyI)-
cyC1-5hexyI]-3-methyIbenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(2-
fluorophenoxy)nicotinamide;
N-(cis-4-{[4-(dimethylammo)-6-niethylpyrimidin-2-yI]amino}cyclohexyl)-3,4)5-
trimethoxybenzam ide;
N-(4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}cyclohexyl)-3-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-2,2-
diphenylacetamide;
N-(cis-4-{[4-(dimethyIamino)-6-methy!pyrimidin-2-yl]amino}cyclohexyl)-4-
methylbenzamide;
4-chloro-N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
3-chloro-N-(cis-4-{[4-(dimethyIammo)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-

247
benzamide;
N-(cis-4-{[4-(dimethy]amino)-6-methylpyrimidin-2-yl]amino}cyclohexyI)-3,4-
d ifluorobenzam ide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
methy I benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}cyC1-5hexyI)-3-
methoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-4-
fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyC1-5hexyl)-3-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
methoxy benzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yI]amino}cyclohexyl)-4-
methylbenzamide;
N-(cis-4-{[4-(dimethy]amino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3,4-
difluorobenzamide;
3-chloro-N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(dimethy]amino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-2-(3-
methylphenoxy)nicotinamide;
2-(4-bromophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)nicotinamide;
2-(4-chIorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amtno}-
cyclohexyl)nicotinamide;
N-(cis-4-{[4-{dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(4-
fluorophenoxy)nicotinamide;
N-(cis-4-{[4-(dimethy]amino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(3-

248
fluorophenoxy)nicotinamide;
2-(2-bromophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}-
cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyC1-5hexyI)-2-(3-
methoxyphenoxy)nicotinamide;
N-(cis-4-{[4-(dimethy]amino)-5-methyIpyrimidin-2-yl]amino}cyC1-5hexyl)-2-(4-
methoxyphenoxy)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(4-
iodophenoxy)nicotinamide;
2-(3;4-dichlorophenoxy)-N-(cis-4-{[5-methyl-4-(methylamino)pyrimidin-2-yl]amino}-
eye lo hexy l)acetam ide;
2-(2,3-dichlorophenoxy)-N-(cis-4-{[5-methyI-4-(methylamino)pyrimidin-2-yl]amino}-
cyclohexyl)acetamide;
2-[(3,4-difluorophenyI)sulfonyI]-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yI]-
amino} cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-ethyIpyrimidin-2-yl]amino}cyclohexyI)-354-
d i fluorobenzam id e;
N-[cis-4-({4-[ethyl(methyI)amino]-5-methylpyrimidin-2-yl}amino)cyclohexyl]-354-
difiuorobenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}cyclohexyl)-3,5-
d imethoxybenzam ide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(2-
methoxyphenoxy)nicotinamide;
2-(2-chlorophenoxy)-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)nicotinamide;
2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyi)nicotinamide;
2-(3-bromophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-

249
cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethyIamtno)-5-methylpyrimidin-2-yl]amino}cyC1-5hexy])-2-[3-
(trifluoromethyl)phenoxy]nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-2-(3-
fluorophenoxy)acetamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(3-
methoxyphenoxy)acetamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-2-[3-
(trifluoromethyl)phenoxy]acetamide;
2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}-
cyclohexyl)acetamide;
2-[(5-chloropyridin-3-yl)oxy]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]-
am ino} eye lohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3,4-
difluorobenzam ide;
2-(3,4-difluorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)-2-hydroxyacetamide;
N-(cis-4-{[4-(dimethyiamino)-5-methy!pyrimidin-2-yl]amino}cyC1-5hexyl)-2-hydroxy-2-(4-
m ethoxypheny l)acetam ide;
2-(2,3-difiuorophenyI)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)-2-hydroxyacetamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-2-hydroxy-2-[3-
(trifluoromethyl)phenyl]acetamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-y]]amino}cyclohexyl)-2-{[2-
(trifluoromethyl)phenyl]sulfmyl}acetamide;
2-[(2-chlorophenyl)sulfinyl]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyl)acetamide;
2-[(3-bromophenyl)sulfinyl]-N-(cis-4-{[4-(dimethylamino)-5-methy]pyrimidin-2-yl]amino}-

250
cyclohexyl)acetamide;
2-[(3,4-difluorophenyI)sulfinyI]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]-
amino} cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yI]amino}cyclohexyl)-3-
(trifluoromethyi)benzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
fluorobenzamide;
1- bromo-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-y]]amino}cyclohexyl)
benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-4-
(trifluoromethoxy)benzamide;
N~(cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
fluorobenzamtde;
3,4-dichIoro-N-(cis-4-{[4-(dimethylamino)-5-methyipyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
bis(trifluoromethy I)benzam ide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
d imethoxybenzam ide;
N-(cis-4- {[4-(dimethy lam ino)-5-methylpyrim id in-2-yl] amino} cyclohexyl)-2,4-
difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2,5-
difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methy!pyrimidin-2-y]]amino}cyclohexyl)-2,3,4-
trifluorobenzamide;
4-chloro-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-
benzamide;
3-cyano-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyC1-5hexyl)-

251
benzamide;
4-cyano-N-(cis-4-{[4-(dimethyiamino)-5-methyIpyrimidin-2-yl]amino}cyC1-5hexyl)-
benzamide;
2-[(3,4-dichlorophenyI)suIfinyl]-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]-
amino}cyclohexyl)acetamide;
N-(cis-4- {[4-(dimethyIamino)-5-methyIpyrimidin-2-y ljamino} cyclohexyI)-2- {[3-
(trifluoromethy])phenyl]sulfinyl}acetamide;
N-(cis-4- {[4-(dimethy Iamino)-5-methyIpyrimidin-2-y l]amino} cyclohexyl)-2- {[3-
(trifluoromethyl)phenyl]sulfonyi}acetamide;
N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yl]amino}cyC1-5hexyl)-2-
(isopropylthio)nicotinamide;
2-(tert-butylthio)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(propylthio)-
nicotinamide;
N-(cis-4-{[4-(diniethyIamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-3-
(methylsulfonyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yI]amino}cyclohexyl)-3-
fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethyl)benzamide;
3-cyano-N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
4-cyano-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dirnethylpyrimidin-2-yI]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yI]amino}cyC1-5hexyl)-3-
(tr i fl uoromethy l)ben zam ide;

252
3-cyano-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
methy I benzamide;
3-chloro-N-(cis-4-{[4-(dimethyIamino)-5,6-dimethyIpyrimidin-2-y]]amino}cyclohexyl)-
benzamide;
3-bromo-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimtdin-2-yl]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(dimethylamino)-5;6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
dimethoxy benzamide;
N-(cis-4-{[4-(dimethy!amino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
bis(trifluoromethyl)benzamide;
3,4-dichloro-N-(cis-4-{[4-(dimethylamino)-5,6-dimethyIpyrimidin-2-yl]amino}cyC1-5hexyI)-
benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyI)-4-
(tri fl uoromethoxy)be nzamide;
4-cyano-N-(cis-4-{[4-(dimethylamino)-5;6-dimethylpyrimidin-2~y]]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yI]amino}cyclohexyl)-4-
methy Ibenzam ide;
N-(cis-4-{[4-(dimethyiamino)-5,6-dimethyIpyrimidin-2-yl]amino}cyclohexyI)-4-
fluorobenzamide;
4-chloro-N-(cis-4-{[4-(dimethyIamino)-5,6-dimethyIpyrimidin-2-yl]amino}cyC1-5hexyl)-
benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethy!pyrimidin-2-yI]amino}cyC1-5hexyl)-2-
methoxybenzamide;
4-bromo-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyc]ohexyI)-
benzamide;

253
N-(cis-4-{[4-(dimethyiamino)-5-methyipyrimtdin-2-yl]amino}cyC1-5hexyI)-4-
(trifluoromethyl)benzamide;
N-(cis-4-{[4-{dimethyiamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
methoxybenzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5,6-diraethylpyrimidin-2-yl]amino}cyclohexyl)-2-
furamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yI]amino}cyclohexyI)-5-
m ethyl isoxazole-3-carboxamide;
2-(3,5-difluorophenyI)-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}-
cyclohexyl)-2-hydroxyacetamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-2-methyl-l,3-
oxazoIe-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexy!)-2,6-
dimethoxynicotinamide;
4-bromo-N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethyipyrimidin-2-yl]amino}cyclohexyl)-4-
(trifluoromethyl)benzamide;
4-bromo-N-(cis-4-{[4-(dimethy!amino)-5,6-dimethyIpyrimidin-2-yl]amino}cyclohexyl)-3-
methyl benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-fluoro-4-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yI]amino}cyclohexyl)-4-fluoro-3-
methylbenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
ethylbenzamide;
N-(cis-4-{[4-tdimethyIamino)-5,6-dimethylpyrimidin-2-yI]amino}cyc!ohexyl)-3-
(trifluoromethoxy)benzamide;

254
5-bromo-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-
nicotinamide;
N-(cis-4-{[4-(dimethylamino)'5,6-dimethylpyrimidin-2-yI]amino}cyclohexyl)-5-
methylthiophene-2-carboxamide
N-(cis-4-{[4-(dimethylamino)-5,6-dimethy!pyrimidin-2-yi]amino}cyC1-5hexyl)-6-
(trifluoromethy I)n ic otinam ide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
diethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyC1-5hexyl)-3-
ethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethy)pyrimidin-2-yl]amino}cyclohexyi)-3-
isopropoxybenzamide;
3,5-dichloro-N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-y]]amino}cyC1-5hexyl)-
benzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyC1-5hexyl)-3-
methyl benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-4-
ethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-fluoro-3-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-fIuoro-4-
methy Ibenzam ide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
ethy Ibenzam ide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
bis(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-fluoro-4-
(trifluoromethyl)benzamide;

255
N-(cis-4-{[4-(dimethyIamino)-6-methy]pyrimidin-2-yl]amino}cyC1-5hexyl)-3-fluoro-5-
(trifluoromethyl)benzamide;
3-chIoro-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyi)-4-
fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-4-fluoro-3-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}cyC1-5hexyI)-3-fluoro-4-
methylbenzamide;
3,5-dich]oro-N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-
benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}cyclohexyl)-3-
(trifluoromethoxy)benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}cyclohexyl)-3,5-
difluorobenzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2~yl]amino}cyclohexyl)-3-
methylbenzamide;
N-(cis-4-{[4~(dimethyIamino)-6-methy!pyrimidin-2-yl]amino}cyC1-5hexyl)-3-
ethylbenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
(trifl uoromethy I)benzam ide;
4-bromo-N-(cis-4- {[4-(dimethy Iamino)-6-methyIpyrimidin-2-y l]amino} cyclohexy 1)-
benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
ethylbenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}cyclohexyl)-3,5-
diethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
ethoxybenzam ide;

256
N-(cis-4-{[4-(dimethyiamino)-6-methy]pyrimidin-2-yl]amino}cyclohexyl)-3-
isopropoxybenzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyI)-
nicotinamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}cyclohexyl)-2-
furamide;
5-chloro-N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yI]amino}cyclohexyl)-2-
furamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-3-fluoro-5-
(tr i fluoromethy l)benzam ide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2,2-difluoro-l,3-
benzodioxole-5-carboxamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-3-
ethoxybenzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyI)-3-
isopropoxybenzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-2-
furamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-y]]amino}cyclohexyl)-3,5-
d iethoxybenzam ide;
4-chloro-N-(cis-4-{[4-(dimethy!amino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-3-
(trifluoromethyl)benzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yI]amino}cyclohexyl)-
nicotinamide;
3,4-dichIoro-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyI)-
benzamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
(tr iflu orom eth oxy)benzam ide;

257
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-4-methoxy-3-
(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-4-methoxy-3-
(trifluoromethyl)benzamide;
2-(4-chIorophenyl)-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyl)-2-methyIpropanamide;
l-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)cyclopropanecarboxamide;
l-(4-chloropheny])-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yi]amino}-
cyclohexy l)cyc lob utanec arboxam ide;
l-(2,4-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}-
cyclohexyl)cyclopropanecarboxamide;
2-(4-chIorophenyl)-N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}-
cyclohexyI)-2-methylpropanamide;
l-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexyl)cyclopropanecarboxamide;
l-(4-chlorophenyI)-N-(ciS"4-{[4-(dimethylamino)"6-methylpyrimidin-2-yl]amino}-
cyclohexyl)cyclobutanecarboxamide;
I-(2,4-dich]orophenyl)-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexyl)cyclopropanecarboxamide;
2-[3,5-bis(trifluoromethyl)phenyl]-N-tcis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]-
amino}cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-y]]amino}cyclohexyl)-4-[2,2,2-
trifluoro-1 -hydroxy-1 -(trifluoromethyl)ethyl]benzamide;
2-(4-chloropheny])-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)acetamide;
N-(cis-4- {[4-(dimethy lamino)-5-methylpyrimidin-2-yl]amino} cyclohexy I)-1 -(4-
methylphenyl)cyclopropanecarboxamide;

258
2-(4-chIorophenyl)-N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yl]amino}-
cyc!ohexyl)propanamide;
2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyl)-2-hydroxyacetamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-l-(4-
methoxy pheny ] )cyc 1 opropanecarboxam id e;
N"-t3-chlorophenyl)-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyl)-N2-methylglycinamide;
N2-(3,4-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyC1-5hexyl)-N2-methylglycinamide;
N-(cis-4-{[4-(dimethyIamino)-5-methyipyrimidin-2-yl]amino}cyclohexyl)-N2-methyl-N2-(3-
methylphenyl)glycinamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-y!]amino}cyclohexyl)-N2-(3-
fluorophenyl)-N2-methylglyc inam ide;
N-(cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N2-(4-
fl uorophenyI)-N2-methy Iglyc inam ide;
N2-t4-chlorophenyl)-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexy!)-N2-methylglycinamide;
N"-(3,4-diftuorophenyI)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-y]]amino}-
cyclohexyI)-N2-methy]glycinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N2-(3-
methoxyphenyl)-N2-methyIglyc inam ide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-y]]amino}cyclohexyl)-N2-(4-
methoxyphenyl)-N2-methy Iglyc inam ide;
2-[(3,4-difluorophenyI)amino]-N-(cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-yl]-
amino} cyclohexyl)nicotinamide;
2-(3,4-dichlorophenoxy)-N-(cis-4-{[4-methyl-6-(methylamino)pyrimidin-2-yI]amino}-
cyclohexyl)acetamide;

259
trans-2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)cyclopropanecarboxamide;
trans-2-(3-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)cyclopropanecarboxamide;
trans-2-(3,4-difluorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}-
eye lohexy I)cyc lopropanecarboxam ide;
trans-2-(3;4-dichIorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]-
amino}cyclohexyl)cyclopropanecarboxamide;
trans-2-[3,5-bis(trifluoromethy!)phenyl]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-
2-yl]amino}cyclohexyl)cyC1-5propanecarboxamide;
2-[(4-chlorophenyl)sulfonyl]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]-
amino}cyclohexyl)nicotinamide;
2-[(3-chlorophenyl)sulfony]]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]-
amino} cyclohexyl)nicotinamide;
2-[(4-bromophenyl)sulfonyl]-N-(cis-4-{[4-(dimethylamino)-5-methyIpyritnidin-2-yl]-
amino}cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-2-{[4-
(trifluoromethyl)phenyl]sulfonyl}nicotinamide;
N-(cis-4- {[4-(d imethy lam ino)-5-methylpy rim id in-2-yl] amino} cyc!ohexyl)-2- {[ I -methyl-3-
(trifIuoromethyI)-lH-pyrazoI-5-yI]oxy}acetamide;
2-[(2-chlorophenyl)sulfonyI]-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]-
amino} cyclohexyl)nicotinamide;
2-[(3-chlorophenyI)suIfonyl]-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]-
amino}cyclohexyl)nicotinamide;
3,4-dichloro-N-{cis-4-[(4-methoxy-5-methylpyrimidin-2-yI)amino]cyclohexyl}-
benzamide;
N-[cis-4-(4-dimethyIamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-
nicotinamide;

260
N-[cis-4-(4-dimethylamino-6-methyl-pyrimidin-2-yIamino)-cyclohexyI]-2-phenoxy-
nicotinamide;
3-chIoro-N-[cis-4-{4-dimethylamino-5-methy]-pyrimidin-2-ylamino)-cyC1-5hexyI]-4-
fluoro-benzamide;
4-chloro-N-[cis-4-(4-dimethyIamino-6-methyI-pyrimidin-2-yIamino)-cyC1-5hexyl]-3-
fluoro-benzamide;
3-chIoro-N-[cis-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-cyC1-5hexyl]-5-
fluoro-benzamide;
N-[cis-4-(4-dimethylamino-6-methyl-pyrimidin-2-yIamino)-cyC1-5hexyI]-3,4,5-trifluoro-
benzamide;
3-chloro-4-fluoro-N-[cis-4-(5-methyl-4-methylamino-pyrimidin-2-ylamino)-cyclohexyl]-
benzamide;
4-chloro-N-[cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyC1-5hexyl]-3-
fluoro-benzamide;
3-chloro-N-[cis-4-(4-dimethyIamino-5-methyl-pyrimidin-2-y]amino)-cyclohexyl]-5-
fluoro-benzamide;
N-[cis-4-(4-dimethyIamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-3,4,5-trifluoro-
benzamide;
N-[cis-4-(4-dimethyIamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-3,5-difluoro-
benzamide; and
2-(3,4-difiuoro-phenyI)-N-[cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexyl]-acetamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)methyl]-3,5-
bis(trifluoromethyl)benzamide;
N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyI)methyI]-3,5-

261
dimethoxybenzamide;
N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)methyl]-3-
(tr ifl u oromethy l)ben zam ide;
4-bromo-N-[(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yI]amino}cyclohexyI)-
methyl]-3-methylbenzamide;
3,5-dichIoro-N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-
methyl] benzam ide;
3,4-dichloro-N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-
methyl] benzamide;
3,5-dichloro-N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}methyl)-
cyclohexyl] benzam ide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(2-
fluorophenoxy)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-3,4,5-
trimethoxybenzamide;
N-(4-{[4-(dimethyIamino)-6-methyIpyrimidin-2-yI]amino}cyclohexyl)-3-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyI)-2,2-
diphenylacetamide;
4-chloro-N-(cis-4-{[4-(dimethylaniino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
3-chloro-N-(cis-4-{[4-(dimethyIamino)-6-methyIpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3,4-
difluorobenzamide;
N-(cis-4-{[4-{dimethyIammo)-6-methylpyrimidin-2-yl]amino}cyclohexyI)-3-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}cyclohexyl)-3-
m eth oxy benzam ide;

262
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-4-
fluorobenzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
meth oxybenzam ide;
N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yl]amino}cyC1-5hexyl)-4-
methylbenzamide;
N-(cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-yl]amino}cyc]ohexyl)-3,4-
difluorobenzamide;
3-chloro-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(3-
methylphenoxy)nicotin amide;
2-(4-bromophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}-
cyclohexyl)njcotinamide;
2-(4-chIorophenoxy)-N-(cis-4-{[4-(diraethylamino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-2-(4-
fluorophenoxy)n icotinam ide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(3-
fluorophenoxy)nicotinamide;
2-(2-bromophenoxy)-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpynmidin-2-yl]amino}cyclohexyl)-2-(3-
methoxyphenoxy)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-2-(4-
methoxyphenoxy)n icotinam ide;

263
N-(cis-4- {[4-(dimethylamino)-5-methy lpyrimidin-2-yl]amino} cyclohexyl)-2-(4-
iodophenoxy)nicotinamide;
2-(3,4-dichlorophenoxy)-N-(cis-4-{[5-methyI-4-(methylamino)pyrimidin-2-yl]amino}-
cyclohexyl)acetamide;
2-(2,3-dichlorophenoxy)-N-(cis-4- {[5-methyl-4-(methy lamino)pyrimidin-2-yl]amino} -
cyclohexyl)acetamide;
2-[(3,4-difluorophenyl)suIfonyI]-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]-
amino} cyclohexyl)nicotinamide;
N-[cis-4-({4-[ethyl(methyl)amino]-5-methylpyrimidin-2-yl}amino)cyclohexyI]-3,4-
difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methyipyrimidin-2-yI]amino}cyclohexyl)-3,5-
dimethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(2-
methoxyphenoxy)nicotinamide;
2-(2-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yi]amino}-
cyclohexyl)nicotinamide;
2-(3-chIorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yi]amino}-
cyclohexyl)nicotinamide;
2-(3-bromophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-2-[3-
(trifluoromethyl)phenoxy]nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-2-(3-
fluorophenoxy)acetamide;
N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-2-(3-
methoxyphenoxy)acetamide;
N-(cis-4-{[4-(dimethylamino>5-methylpyrimidin-2-yI]amino}cyclohexyl)-2-[3-
(trifluoromethyl)phenoxy]acetamide;

264
2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)acetamide;
2-[(5-chIoropyridin-3-yl)oxy]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]-
amino}cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yI]amino}cyclohexyl)-3,4-
difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyi)-2-hydroxy-2-(4-
methoxyphenyl)acetamide;
2-(2,3-difIuorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yi]amino}-
eye lohexy l)-2-hydroxyacetami de;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyC1-5hexyl)-2-hydroxy-2-[3-
(trifluoromethyl)phenyl]acetamide;
N-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino} cyclohexy l)-2- {[2-
(trifluoromethyl)phenyl]su]finyl}acetamide;
2-[(2-chlorophenyl)sulfinyI]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)acetamide;
2-[(3-bromopheny!)suIfinyI]-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}-
eye lohexy l)acetamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-3-
(tri fl uoromethy I)benzam ide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
fluorobenzamide;
3-bromo-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(diniethyIamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-4-
(trifluoromethoxy)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI3amino}cyclohexyl)-4-
fluorobenzamide;

265
3,4-dichloro-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyI)-
benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
bis(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-3,5-
dimethoxybenzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-2,4-
difluorobenzamide;
N-(cis-4-{[4-(dimethy!amino)-5-methy]pyrimidin-2-yl]amino}cyC1-5hexyI)-2,5-
difiuorobenzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyI)-2,3,4-
trifluorobenzamide;
4-chloro-N-(cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
3-cyano-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-
benzamide;
4-cyano-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-
benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-2-
(isopropylthio)nicotin amide;
N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yl]amino}cyC1-5hexyl)-2-
(propylthio)nicotinamide;
N-(cis-4'{[4-(dimethylamino)-6-methylpyrimidin-2-y]]amino}cyclohexyl)-3-
(trifluoromethyl)benzamide;
3-cyano-N-(cis-4-{[4-(dimethyIamino)-6-methyIpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
4-cyano-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyC1-5hexyi)-
benzamide;

266
N-(cis-4-{[4-(dimethylamino)-5,6'dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
(tr ifl uorom ethyl)ben zam i de;
3-cyano-N-(cis-4-{[4-(dimethyIamino)-5,6-dimethyIpyrimidin-2-yl]amino}cyclohexyI)-
benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
methy 1 benzam ide;
3-chIoro-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyI)-
benzamide;
3-bromo-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyC1-5hexyl)-
benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
dimethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
bis(trifluoromethyl)benzamide;
3,4-dichloro-N-(cis-4-{[4-(dimethyiamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
4-cyano-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yi]amino}cyclohexyl)-4-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yI]amino}cyclohexyl)-4-
fluorobenzamide;
4-chloro-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyI)-
benzamide;
4-bromo-N-(cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(dimethyIamJno)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
(trifluoromethyt)benzamide;

267
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
methoxybenzamide;
5-bromo-N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyI)-2-
furamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethyIpyrimidin-2-yl]amino}cyclohexyl)-2,6-
dimethoxynicotin amide;
4-bromo-N-(cis-4-{[4-(dimethyIamino)-5,6-dimethyIpyrimidin-2-yl]amino}cyC1-5hexyl)-
benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethyIpyrimidin-2-yl]amino}cyclohexyl)-4-
(trifluoromethyl)benzamide;
4-bromo-N-(cis-4-{[4-(dimethyIamino)-5,6-dimethyIpyrimidin-2-yl]amino}cyC1-5hexyl)-3'
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-fluoro-4-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyI)-4-fIuoro-3-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethoxy)benzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5r6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-
nicotinamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethyIpyrimidin-2-yl]amino}cyclohexyl)-5-
methylthiophene-2-carboxamide;
N-(cis-4-{[4-(dimethyIamino)-5;6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
diethoxy benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyI)-3-
ethoxybenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]amino}cyC1-5hexyl)-3-
isopropoxybenzamide;

268
3,5-dichloro-N-(cis-4-{[4-(dirnethylamino)-5-methylpynmidin-2-yl]amino}cyclohexyl)-
benzamide;
4-bromo-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyc]ohexyI)-3-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-4-fluoro-3-
methylbenzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexy])-3-fluoro-4-
methyl benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-3-
ethylbenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}cyclohexyl)-3,5-
bis(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-fiuoro-4-
(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-fluoro-5-
(trifluoromethyl)benzamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-4-fluoro-3-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}cyclohexyl)-3-fluoro-4-
methylbenzamide;
3,5-dichloro-N-(cis-4-{[4-(dimethyIamino)-6-methyIpyrimidin-2-yI]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methyipyrimidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethoxy)benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}cyclohexyl)-3,5-
difluorobenzamide;

269
4-bromo-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyc!ohexyl)-3-
methyl benzamide;
N-(cis-4-{[4-(dimethyIamino>6-methylpyrimidin-2-y]]amino}cyc]ohexyI)-3-
ethylbenzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)-6-methy]pyrimidin-2-y]]amino}cyclohexyI)-
benzamide;
N-(cis-4-{[4-tdimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
ethylbenzamide;
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
d iethoxybenzam ide;
N~(cis-4-{[4-(dimethylamino)-6-methy]pyrimidin-2-yl]amino}cyclohexyl)-3-
ethoxy benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
isopropoxybenzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-6'methy!pyrimidin-2-yI]amino}cyclohexyl)-
nicotin amide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyI)-2-
furamide;
5-chloro-N-(cis-4-{[4-(dimethyiamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-2-
furamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-3-fluoro-5-
(trifl uoromethy l)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2,2-difluoro-l,3-
benzodioxole-5-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclobexyI)-3-
ethoxybenzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexy])-2-
furamide;

270
N-(cis-4-{[4-(dimethy)amino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-3,5-
diethoxybenzamide;
4-chIoro-N-(cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-yI]amino}cyclohexyI)-3-
(trifluoromethyl)benzamide;
5-bromo-N-(cis-4~{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino)cyclohexyl)-
nicotinamide;
3,4-dichloro-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
3-chloro-N-(cis-4-{[4~(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
(trifluoromethoxy)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-methoxy-3-
(trifiuoromethyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]ammo}cyclohexyl)-4-methoxy-3-
(trifluoromethyl)benzamide;
2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)-2-methyIpropanamide
l-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)cyclopropanecarboxamide;
l-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyi)cyclobutanecarboxamide;
l-(2,4-dichlorophenyi)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyC1-5hexyl)cyclopropanecarboxamide;
2-(4-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
eye lohexy l)-2 -methy 1 propanamide
l-(4-ch]orophenyI)-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexyl)cyclopropanecarboxamide;
l-(4-chlorophenyi)-N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}-
cyclohexyi)cyc]obutanecarboxamide;

271
l-(2,4-dichlorophenyl)-N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin'2-yl]amino}-
cyclohexyl)cyclopropanecarboxamide;
2-(4-chIorophenyl>N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yf]amino}-
cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-l-(4-
methy I pheny I)cyc lopropan ec arboxam ide;
2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethy]amino)-5-methylpyrimidin-2-yi]amino}-
eye loh exy l)propanam ide
2-(4-chloropheny])-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-
eye loh exy l)-2 -hydroxy acetam ide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-l-(4-
methoxyphenyl)cyc lopropan ecarboxam ide;
N"-(3-chlorophenyl)-N-(cis-4-{[4-(dtmethylamino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyl)-N2-methyIgIycinamide;
N2-(3,4-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyI)-N"-methy)glycinamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N2-methyI-N2-(3-
methylphenyl)glycinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-N2-(3-
fluorophenyl)-N2-methylg!ycinamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-N2-(4-
fluorophenyl)-N2-methylglycinamide;
N2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)-N2-methylglycinamide;
N2-(3,4-difluorophenyI)-N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yl]amino}-
cyclohexyl)-N2-methyIg!ycinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N2-(3-
methoxyphenyl)-N2-methylglycinamide;

272
2-(3,4-dichlorophenoxy)-N-(cis-4-{[4-methyl-6-(methylamino)pyrimidin-2-yl]amino}-
cyclohexyl)acetamide;
trans-2-(4-chloropheny])-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)cyclopropanecarboxamide;
trans-2-(3-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)-5-methy]pyrimidin-2-yl]amino}-
cyclohexyl)cyclopropanecarboxamide;
trans-2-(3,4-diftuorophenyI)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyl)cyC1-5propanecarboxamide;
trans-2-(3,4-dichIorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]-
amino}cyclohexyl)cyclopropanecarboxamide;
trans-2-[3,5-bis(trifluoromethyl)phenyl]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-
2-yl]amino}cyclohexyl)cyC1-5propanecarboxamide;
2-[(4-chlorophenyl)suIfonyl]-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yI]-
amino} cyclohexy l)rricotinamide;
N-(cis-4-{[4-(dimethy!amino)-5'methyIpyrimidin-2-yI]amino}cyclohexyl)-2-{[l-methyl-3-
(trifluoromethyl)-lH-pyrazol-5-yl]oxy}acetamide;
N-[cis-4-(4-dimethyIamino-5-methyI-pyrimidin-2-ylamino)~cyclohexyl]-2-phenoxy-
nicotinamide;
N-[cis-4-(4-dimethyIamino-6-methyI-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-
nicotinamide;
3-chloro-N-[cis-4-(4-dimethyIamino-5-methyI-pyrimidin-2-ylamino)-cyC1-5hexyl]-4-f!uoro-
benzamide;
4-chloro-N-[cis-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-cyclohexyl]-3-fluoro-
benzamide;
3-chIoro-N-[cis-4-(4-dimethyIamino-6-methyl-pyrimidin-2-y)amino)-cyclohexyl]-5-fluoro-
benzamide;
N-[cis-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-cyc]ohexyl]-3,4,5-trifluoro-
benzamide:

273
3-chIoro-4-fluoro-N-[cis-4-(5-methyi-4-methyIamino-pyrimidin-2-ylamino)-cyclohexyl]-
benzamide;
4-chloro-N-[cis-4-(4-dimethyIamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-3-fIuoro-
benzamide;
3-chloro-N-[cis-4-(4-dimethyIamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-5-fluoro-
benzamide;
N-[cis-4"{4-dimethylamino-5-methyI-pyrimidin-2-ylamino)-cyclohexy)]-3,4,5-trifluoro-
benzamide;
N-[cis-4-(4-dimethyIamino-5'methyl-pyrimidin-2-ylamino)-cyclohexyl]-3,5-difluoro-
benzamide; and
2-(3,4-difluoro-phenyl)-N-[cis-4-(4-dimethyIamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexylj-acetamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, R[ is selected from the group consisting of:
(i) C1-16 alkyl, and
C].t6 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,
••Ci.s alkyIcarbonylamino,
"C3-6 cycloalkylcarbonylamino,
»C1-5 alkyl,
••Ct-s alkyl substituted by halogen,
••C1-5 atkoxy, and
"C:_5 alkoxy substituted by halogen,

274
(") C3.12 cycloalkyl, and
C3-12 cycloalkyl substituted by carbocyclic aryl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-50 alkyl,
•Ci-io alkyl substituted by halogen,
•C]_9 alkoxy, and
•C1-5 alkylthio,
(iv) heterocyclyl,
L is Formula (XV);
Y is -C(O)NR5-;
R2 is selected from the group consisting of:
-N(R2a)(R2t)), wherein R2a is hydrogen or C1-5 alkyl and R2b is C1-5 alkyl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is 3,4-dihydro-l//-isoquinolinyl; and
halogen is fiuoro, chloro, bromo, or iodo;
or a pharmaceuticaliy acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Ri is selected from the group consisting of:
(i) C]-i6 alkyl, and
Cj.16 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,

275
••C1-5 alkyl,
"C1-5 alkyl substituted by halogen,
"•C1-5 alkoxy, and
"Cj.5 alkoxy substituted by halogen,
(ii) C3-12 cycloalky!, and
C3-12 cycloalkyl substituted by carbocyclic aryl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•CLIO alkyl,
•C1-5O alkyl substituted by halogen, and
•C].9 alkoxy,
R2 is selected from the group consisting of:
-N(R2a)(R.2bX wherein R2a is hydrogen or d.5 alkyl and R2b is C\.5 alkyl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is 3,4-dihydro-l//-isoquinolinyI; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, p is 1 and T is C1-5 alkyl; R3 and R4 are both
hydrogen; and A and B are both single bonds; R5 is hydrogen: or a pharmaceutically acceptable salt,
hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}-N-(3-iodobenzyI)-
cyclohexanecarboxamide;
cis-N-(2,4-dichlorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexanecarboxamide;

276
cis-N-(2,5-dichlorobenzyl)-4-{[4-(dimethylamino)-6-methyIpyrimidin-2"yI]amino}-
cyclohexanecarboxamide;
cis-4-{[4~(dimethylamino)-6-methyipyrimidin-2-yl]amino}-N-(4-methyIbenzyl)-
cyclohexanecarboxamide;
cis-N-(3,5-dichlorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexanecarboxamide;
cis-N-(3,5-dimethoxybenzyI)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexanecarboxamide;
cis-N-(3-chlorobenzyl)-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-[3-(trifluoromethyl)benzyl]-
cyclohexanecarboxamide;
cis-N-[3,5-bis(trifluoromethyI)ben2yl]-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]-
amino}cyclohexanecarboxamide;
cis-4- {[4-(dimethyIamino)-6-methylpyrimidin-2-y l]amino} -N-(3-methoxybenzyl)-
cyclohexanecarboxamide;
cis-N-(4-chlorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}-
cyclohexanecarboxamide;
cis-N-(3,4-dichlorobenzyI)-4-{[4-(dimethylammo)-6-methylpyrimidin-2-yI]amino}-
cyclohexanecarboxamide;
cis-N-(2,5-difluorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexanecarboxamide;
cis-N-(2,3-difluorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexanecarboxamide;
cis-N-(4-bromo-2-fluorobenzyI)-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexanecarboxamide;
cis-N-(2,4-difluorobenzyI)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexanecarboxamide;

277
cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yi]amino}-N-(3-methylbenzyl)-
cyclohexanecarboxamide;
cis-4-{[4-(dimethyIamino)-6-methy]pyrimidin-2-yl]amino}-N-[2-(trifiuoromethoxy)benzyl]-
cyclohexanecarboxamide;
cis-4- {[4-(dimethyIamino)-5-methy lpyrimidin-2-yl]amino} -N-[(l R)-1 -phenylethyl]-
cyc lohexanecarboxam id e;
cis-4- {[4-(di methyl amino)-5-methy lpyrimidin-2-yI]amino} -N-[( 1S)-1 -(4-methy Ipheny I)-
ethyljcyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}-N-[(lR)-l-(4-fluorophenyl)-
ethy 1] eye lohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lS)-l-{4-fluorophenyl)-
ethyljcyclohexanecarboxamide;
cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino} -N-[( 1 R)-l -(3-methoxyphenyl)-
ethyl]cyC1-5hexanecarboxamide;
cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yI]amino}-N-[(lS)-l-(3-methoxyphenyI)-
ethyl] eye lohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lS)-l-(4-methoxyphenyl)-
ethyljcyclohexanecarboxamide;
cis-N-[( 1R)-1 -(4-chIorophenyl)ethyI]-4-{ [4-(dimethylamino)-5-methy lpyrimidin-2-y I]-
amino} cyclohexanecarboxamide;
cis-N-[l-(4-bromophenyl)ethyl]-4-{[4-(dimethylamino)'5-methylpyrimidin-2-yl]amino}-
cyc lohexanec arboxam ide;
cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-N-[(lR)-l-(4-nitrophenyl)-
ethyljcyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lS)-l-(4-nitrophenyl)ethyl3-
cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-(3-fluorophenyl)-
cyclohexanecarboxamide;

278
ciS'4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yl]amino}-N-(3-methoxyphenyl)-
cyclohexanecarboxamide;
cis-N-(3-chlorophenyl)-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}-
cyc lohexanecarboxam ide;
cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}-N-[(lS,2R)-2-
phenylcyclopropyl]cyclohexanecarboxamide;
cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-N-[4-(trifluoromethyl)phenyl]-
cyclohexanecarboxamide;
cis-4- {[4-(dimethylamino)-6-methy lpyrimidin-2-y l]amino} -N-[( 1R)-1 -(3-methoxyphenyl)-
ethyl] cyclohexanecarboxamide;
cis-N-[(lS)-l-(4-chlorophenyl)ethyl]-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]-
amino} cyclohexanecarboxamide;
cis-N-benzyl-4- {[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino} -
cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}-N-(4-fluorobenzyl)-
cyclohexanecarboxamide;
cis-N-(3,4-difluorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-[(lS)-l-(4-methoxyphenyl)-
ethyl] eye lohexanecarboxam ide;
cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}-N-[(lS)-l-(3-methoxyphenyl)-
ethyl] eye lohexanecarboxam ide;
cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-[(lR)-l-(4-fluorophenyl)-
ethy 1] eye lohexanecarboxamide;
cis-N-[( 1R)-1 -(4-chloropheny l)ethyl]-4- {[4-(dimethylamino)-6-methylpyrimidin-2-y 1]-
amino} cyclohexanecarboxamide;
cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-y l]amino} -N-[( 1S)-1 -(1 -naphthyl)ethy 1]-
cyc lohexanecarboxamide;

279
cis-N-[(lR)-l-(4-bromophenyl)ethyl]-4-{[4-tdimethyJamino)-5-methyIpyrimidin-2-yl]-
amino}cyclohexanecarboxamide;
cis-N-[(lS)-l-(4-bromophenyI)ethy!]-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]-
amino}cyclohexanecarboxamide;
cis-4-{ [4-(dimethylamino)-5-methylpyrimidin-2-y l]amino} -N- {(1S)-1 -[4-
(trifluoromethoxy)phenyl]ethyl}cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lR)-l-(2-fluoropheny])-
ethyljcyclohexanecarboxamide;
cis-N-{(lS)-l-[3,5-bis(trifluoromethyI)phenyl]ethyl}-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexanecarboxamide;
4-{[4-(dimethylamino)-5-methylpyrimidin-2-yi]amino}-N-{(lS)-J-[3-(trifluoromethyl)-
phenyI3ethyl}cyclohexanecarboxamide;
4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yi]amino}-N-{(lS)-l-[2-(trifluoromethyI)-
phenyl]ethyl}cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yI]amino}-N-{(lR)-l-[4-
(trifluoromethoxy)phenyl]ethyl}cyclohexanecarboxamide;
cis-N-[(lS)-l-(4-chlorophenyi)ethyl]-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]-
amino}cyclohexanecarboxamide;
cis-N-[(lR)-l-(4-chIorophenyI)ethyl]-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]-
amino}cyclohexanecarboxamide;
cis-N-[l-(4-chlorophenyI)-l-methyIethyl]-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]-
amino}cyclohexanecarboxamide; and
cis-N-{l-[3,5-bis(trifluoromethy])phenyI]-I-methyIethyl}-4-{[4-(dimethylamino)-5-
methyIpyrimidin-2-yl]amino}cyclohexanecarboxamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
cis-4~{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-(3-iodobenzyl)-

280
cyclohexanecarboxamide;
cis-N-(2,4-dichlorobenzyl)-4-{[4-(dimethyIamino)-6-methyipyrimidin-2-yl]amino}-
eye lohexanecarboxam ide;
cis-N-(2,5-dichIorobenzyI)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}-
cyc lohexanecarboxam ide;
cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}-N-(4-methylbenzyI)-
cyclohexanecarboxamide;
cis-N-(3,5-dichloroben2yl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
cy c lohe xanec arboxam ide;
cis-N-(3,5-dimethoxybenzyI)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
eye lohexanec arboxam ide;
cis-N-(3-chlorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin~2-yl]amino}-
cyclohexanecarboxamide;
cis-N-[3,5-bis(trifluoromethyl)benzyl]-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]-
amino} cyclohexanecarboxamide;
cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}-N-(3-methoxybenzyl)-
cyclohexanecarboxamide;
cis-N-(4-chlorobenzyI)-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}-
cyc lohexanec arboxam ide;
cis-N-(3,4-dichIorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexanecarboxamide;
cis-N-(2,5-difluorobenzyl)-4-{[4-(dimethyiamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexanec arboxam ide;
cis-N-(2,3-difluorobenzyl)-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}-
cyclohexanecarboxamide;
cis-N-(4-bromo-2-fluorobenzyi)-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}-
cyclohexanecarboxamide;
cis-N-(2,4-difluorobenzyi)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-

281
cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-(3-methylbenzyl)-
cyclohexanecarboxamide;
cis-4-{[4-(dimethyiamino)-6-methylpyrimidin-2-yl]amino}-N-[2-(trifluoromethoxy)benzyI]-
cyclohexanecarboxamide;
cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2~yl]amino}-N-[(lS)-l-(4-methyIphenyl)-
ethyl]cyclohexanecarboxamide;
cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yI]amino}-N-[(lR)-l-(4-fluorophenyl)-
ethyljcyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lR)-l-(3-methoxyphenyI)-
ethyl] cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lS)-l-(3-methoxyphenyl)-
ethy 1] cy c lohexanec arboxam ide;
cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-N-[(lS)-l-(4-methoxyphenyl)-
ethyljcyclohexanecarboxamide;
cis-N~[(lR)-l-(4-chlorophenyI)ethyi]-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]-
amino} cyclohexanecarboxamide;
cis-N-[l-(4-bromophenyl)ethyl]-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexanecarboxam ide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lR)-l-(4-nitrophenyI)-
ethyl]cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-(3-methoxyphenyI)-
cyclohexanecarboxamide;
cis-N-(3-chlorophenyl)-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yI]amino}-
cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lS,2R)-2-
phenylcyclopropyljcyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[4-(trifluoromethyl)phenyI]-

282
cyclohexanecarboxamide;
cis-N-[(lS)-l-(4-chlorophenyl)ethyl]-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]-
amino}cyclohexanecarboxamide;
cis-N-(3,4-difluorobenzyl)-4- {[4-(dimethyIamino)-6-methy lpyrimidin-2-yI]amino} -
cyclohexanecarboxamide;
cis-4-{[4-(dimethy]amino)-6-methyipyrimidin-2-yl]amino}-N-[(lS)-I-(4-methoxyphenyI)-
ethyl] eye lohexanecarboxamide;
cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-[(lS)-l-(3-methoxyphenyl)-
ethyljcyc lohexanecarboxamide;
cis-N-[(lR)-l'(4-chlorophenyl)ethyI]-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]-
amino} cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lS)-l-(l-naphthyl)ethyl]-
cyclohexanecarboxamide;
cis-N-[(lS)-l-(4-bromophenyl)ethyl]-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]-
amino}cyclohexanecarboxamide;
cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-N-{(lS)-l-[4-
(trifluoromethoxy)phenyl]ethyl}cyclohexanecarboxamide;
cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino} -N-[( 1R)-1 -(2-fluorophenyl)-
ethyl] eye lohexanecarboxamide;
cis-N-{(lS)-l-[3J5-bis(trifluoromethyl)phenyI]ethyl}-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexanecarboxamide;
4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-{(lS)-l-[3-(trifIuoromethyl)-
phenyl]ethyl} cyclohexanecarboxamide;
4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-{(lS)-l-[2-(trifluoromethyI)-
phenyljethyl}cyclohexanecarboxamide; and
cis-N-[(lR)-l-(4-chloropheny!)ethyl]-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]-
amino} cyclohexanecarboxamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.

283
In some embodiments of the present invention, Rj is selected from the group consisting of:
(i) C1-16 alkyl, and
Ci_i6 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
"C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
(ii) C3_|2 cycloalkyl, and
C3-12 cycloalkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by halogen,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5O alkyl,
"Ci-io alkyl substituted by halogen,
•C1-9 alkoxy,
•C1.9 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
"halogen, and
••carbocyclic aryl,
L is Formula (VII);
Y is -C(O)NR5-;

284
R2 is -N(R2a)(R2b) wherein R2a is hydrogen or C1-5 alkyl and R2b is C1-5 alkyl;
wherein carbocyclic aryl is phenyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, p is 1 or 2 and each T is independently C1-5
alkyl; R3 is hydrogen; R4 is hydrogen or C1-5 alkyl; A and B are both single bonds; R5 is hydrogen: or
a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
N-(354-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]-
amino}cyclohexyl)urea;
N-(3-chlorophenyl)-N'-tcis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyl)-N-methylurea;
N-(3,4-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cydohexyl)-N-methylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-methyl-N-{3-
methy lpheny l)urea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-methyl-N-(4-
methylphenyl)urea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-(3'
fluorophenyl)-N-methylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyC1-5hexyl)-N-(4-
fluorophenyl)-N-methylurea;
N-(4-chlorophenyl)-N'-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)-N-methylurea;
N-(3,4-difluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)-N-methylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-(3-

285
methoxyphenyl)-N-methylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-(4-
methoxypheny])-N-methyIurea;
N-{l-[3,5-bis(trifluoromethyI)phenyl]-I-methylethyl}-N'-(cis-4-{[4-(dimethyIamino)-5-
methylpyriraidin-2-yl]amino}cyclohexyl)urea;
N-[l-(4-chlorophenyl)-I~methylethyl]-N'-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)urea;
N-[l-(4-chlorophenyl)-l-methylethyl]-N'-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yljamino} cyclohexyl)urea;
N-[ 1 -(4-chlorophenyI)-1 -methy lethy l]-N'-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-
yI]amino}cyclohexyl)-N-methylurea;
N-[ 1 -(4-chlorophenyl)-1 -methy lethy ]]-N'-(cis-4- {[4-(dimethy lamino)-6-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)-N-methylurea;
N-[l-(4-chIorophenyl)cyclopropyi]-N'-(cis-4-{[4-(dimethy!amino)-5-methylpyrimidin-2-yl]-
amino}cyC1-5hexyl)-N-methylurea;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N'-(2-
methoxyphenyl)urea;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-N'-(3-
methoxyphenyl)urea;
N-(3,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}-
cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-N'-(4-
fluorophenyl)urea;
N-(3,4-difluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N'-[2-
(trifluoromethoxy)phenyl]urea;
N-(4-chlorophenyl)-N'-{cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-

286
cyclohexyl)urea;
N-[3,5-bis(trifluoromethyI)phenyl]-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]-
amino}cyclohexyl)urea;
N-(4-bromopheny])-N'-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)urea;
N-(cis-4-{[4-tdimethyIamino)-5-methy!pyrimidin-2-yl]amino}cyclohexyI)-N'-(2-
methylphenyl)urea;
N-benzyl-N'-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)urea;
N-[2-chloro-6-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-
2-yl]amino}cyclohexyI)urea;
N-(cis-4-{[4-(dimethy]amino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N'-(2,4,6-
trichlorophenyl)urea;
N-(2,4-dichlorophenyI)-N'-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)-N-methyIurea;
N'-(cis-4-{[4-(dimethy]amino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-N-methyl-N-[2-
(trifluoromethoxy)pheny 1] urea;
N-(4-chIoropheny!)-N'-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-y!]amino}-
eye iohexyI)-N-ethy] urea;
N-[3,5-bis(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethylamino)-5-methylpyritnidin-2-
yi]amino}cyclohexyl)-N-ethyIurea;
Nt-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-N-(2-
fluorophenyl)-N-methylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-N-ethyl-N-[2-
(trifluoromethoxy)phenyl]urea;
N'-(cis-4-{[4-(dimethylammo)-5-methylpyrimidin-2-yi]amino}cyclohexyl)-N-ethyl-N-
phenylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-ethyl-N-(3-
methylphenyl)urea; and

287
l-(2,3-dichloro-phenyl)-3-[cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexylmethyl]-urea;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments, compounds of the present invention are of Formula (I) wherein the
compound is selected from the group consisting of:
N-(3,4-dimethoxyphenyI)-N'-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]-
amino}cyclohexyl)urea;
N-(3-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-y]]amino}-
cyclohexyl)-N-methylurea;
N-(3,4-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)-N-methylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-N-methyl-N-(3-
methylphenyl)urea;
N'-(cis-4- {[4-(dimethy lamino)-5-methylpyrimidin-2-y l]amino} cyclohexyl)-N-methyl-N-(4-
methylphenyl)urea;
N'-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-(3-
fluorophenyl)-N-methylurea;
N'-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-(4-
fluorophenyl)-N-methylurea;
N-(4-chlorophenyl)-N'-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)-N-methylurea;
N-(3,4-difluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyl)-N-methylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-(3-
methoxyphenyl)-N-methylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-N-(4-
methoxyphenyI)-N-methykirea;
N-[l-(4-chlorophenyl)-l-methylethyl]-N'-{cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-

288
yl]amino}cyclohexyl)urea;
N-[l-(4-chlorophenyI)-l-methylethyl]-N'-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-
yl]amino}cyclohexyl)urea;
N-[l-(4-chlorophenyl)-]-methylethyi]-N'-(cis-4-{E4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexy])-N-methylurea;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyC1-5hexyl)-N'-(4-
fiuorophenyl)urea;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N'-[2-
(trifluoromethoxy)phenyl]urea;
N-(4-bromophenyl)-N'-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yl]amino}-
cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yI]amino}cyclohexyI)-N'-(2-
methylphenyl)urea;
N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yl]amino}cyC1-5hexyl)-N'-(2,4,6-
trichlorophenyl)urea;
N-(2,4-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)-N-methylurea;
N'-(cis-4-{[4-tdimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-methyl-N-[2-
(trifluoromethoxy)phenyl]urea;
N-(4-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yI]amino}-
eye lohexyI)-N-ethyl urea;
N-[3,5-bis(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyctohexyl)-N-ethylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyriraidin-2-yl]amino}cyclohexyl)-N-ethyI-N-
phenylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-N-ethyl-N-(3-
methylphenyl)urea; and
l-(2,3-dichloro-phenyl)-3-[cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-

289
eye lohexylm ethyl]-urea;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, Ri is selected from the group consisting of:
heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
"halogen, and
"C1-5 alkoxy,
L is Formula (X) or (XI);
Y is -C(O)-;
R? is -N(R2a)(R2b) wherein R2a is C1-5 alkyl and R2b is C1-5 alkyl;
wherein carbocyclic aryl is phenyl;
heterocyclyl is pyridyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, p is 1 and T is C1-5 alkyl; R3 and R4 are both
hydrogen; A is a single bond and B is -CH2-; or a pharmaceutically acceptable salt, hydrate, or solvate
thereof.
In some embodiments of the present invention, R] is selected from the group consisting of:
(i) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5O alkyl, and
•Q.io alkyl substituted by halogen,

290
(ii) heterocyclyl,
L is Formula (VII); and
Y is -S(O)r;
R2 is -N(R2a)(R2b) wherein R2a is C1-5 alkyl and R2b is C1-5 alkyl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is ftiryl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, p is 1 and T is C1-5 alkyl; R3 and R4 are both
hydrogen, and A and B are both single bonds; or a pharmaceutically acceptable salt, hydrate, or
solvate thereof.
In some embodiments, a compound of the present invention is:
4-chloro-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-ylIamino}cyclohexyI)-
benzenesulfonamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
In some embodiments of the present invention, wherein Ri is selected from hydrogen,
-CO2fBu, or -CO2Bn (Bn is a benzyl group);
R2 is selected from the group consisting of:
hydrogen, halogen, hydroxy, carboxy, carbamoyl, amino, Cj.5 alkyl, C1-5
alkyl substituted by halogen, C1-5 alkyl substituted by hydroxy, C1-5 alkyl substituted
by carboxy, C1-5 alkyl substituted by carbamoyl, C1-5 alkoxy, Cj_5 alkoxy substituted
by halogen, -N(R2a)(R2b);
wherein R2a is hydrogen or C1-5 alkyl and R2b is C1-5 alkyl, C3-6 cycloalkyl, or C1-5 alkyl
substituted by substituent(s) independently selected from the group consisting of:
•halogen,
•hydroxy,
•carboxy,
•carbamoyl,

291
•C[.5 alkoxy,
•amino,
"C3-6 cycloalkyl,
or R2 is methylamino or dim ethyl amino when Q is Formula (II);
Each T is independently selected from the group consisting of halogen, hydroxy,
carboxy, carbamoyl, amino, cyano, nitro, Cj.s alkyl, C1-5 alkyl substituted by halogen,
C1-5 alkyl substituted by hydroxy, C1-5 alkyl substituted by carboxy, d.5 alkyl
substituted by carbamoyl, C2-5 alkenyl, C2.5 alkynyl, C^e cycloalkyl, C1-5 alkoxy, C1-5
alkoxy substituted by halogen, carbocyclic aryl, heterocyclyl, and -N(R2a)(R7b);
pisO, 1,2, 3, 4 or 5;
L is selected from the group consisting of Formula (VII), (X), (XI), (XV), (XVIII), or
(XIX): wherein R3 and R4 are independently hydrogen or Ct.5 alkyl; and A and B are
independently a single bond or -CH2-; and
Y is a single bond;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
One aspect of the present invention pertains to pharmaceutical compositions comprising at
least one compound, as described herein, in combination with a pharmaceutically acceptable carrier.
One aspect of the present invention pertains to methods for the prophylaxis or treatment of
improving memory function, sleeping and arousal, anxiety, depression, mood disorders, seizure,
obesity, diabetes, appetite and eating disorders, cardiovascular disease, hypertension, dyslipidemia,
myocardial infarction, binge eating disorders including bulimia, anorexia, mental disorders including
manic depression, schizophrenia, delirium, dementia, stress, cognitive disorders, attention deficit
disorder, substance abuse disorders and dyskinesias including Parkinson's disease, epilepsy, and
addiction comprising administering to an individual suffering from the condition a therapeutic ally
effective amount of a compound, as described herein, or a pharmaceutical composition thereof.
One aspect of the present invention pertains to methods for the prophylaxis or treatment of an
eating disorder, obesity or an obesity related disorder comprising administering to an individual
suffering from the condition a therapeutically effective amount of a compound, as described herein,

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or a pharmaceutical composition thereof.
One aspect of the present invention pertains to methods for the prophylaxis or treatment of
anxiety, depression, schizophrenia, addiction, or epilepsy comprising administering to an individual
suffering from the condition a therapeutically effective amount of a compound, as described herein,
or a pharmaceutical composition.
One aspect of the present invention pertains to compounds of the present invention, as
described herein, or a pharmaceutical composition thereof, for use in a method of treatment of the
human or animal body by therapy.
One aspect of the present invention pertains to compounds of the present invention, as
described herein, or a pharmaceutical composition thereof, for use in a method of prophylaxis or
treatment of an eating disorder, obesity or an obesity related disorder of the human or animal body by
therapy.
One aspect of the present invention pertains to compounds of the present invention, as
described herein, or a pharmaceutical composition thereof, for use in a method of prophylaxis or
treatment of anxiety, depression, schizophrenia, addiction, or epilepsy of the human or animal body
by therapy.
One aspect of the present invention pertains to compounds of the present invention, as
described herein, for the manufacture of a medicament for use in the prophylaxis or treatment of an
eating disorder, obesity or obesity related disorders.
One aspect of the present invention pertains to compounds of the present invention, as
described herein, for the manufacture of a medicament for use in the prophylaxis or treatment of
anxiety, depression, schizophrenia, addiction, or epilepsy.
One aspect of the present invention pertains to methods of decreasing food intake of an
individual comprising administering to the individual a therapeutically effective amount of a
compound, as described herein, or a pharmaceutical composition thereof.
One aspect of the present invention pertains to methods of inducing satiety in an individual
comprising administering to said individual a therapeutically effective amount of a compound, as
described herein, or a pharmaceutical composition thereof.

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One aspect of the present invention pertains to methods of controlling or reducing weight gain
in an individual comprising administering to said individual a therapeutically effective amount of a
compound, as described herein, or a pharmaceutical composition thereof.
One aspect of the present invention pertains to methods of modulating a MCH receptor in an
individual comprising contacting the receptor with a compound, as described herein. In some
embodiments, the compound is an antagonist. In some embodiments, the modulation of the MCH
receptor is for the prophylaxis or treatment of an eating disorder, obesity or obesity related disorder.
In some embodiments, the modulation of the MCH receptor reduces food intake of the individual. In
some embodiments, the modulation of the MCH receptor induces satiety in the individual. In some
embodiments, the modulation of the MCH receptor controls or reduces weight gain of the individual.
In some embodiments, the modulation of the MCH receptor is for prophylaxis or treatment of anxiety,
depression, schizophrenia, addiction, or epilepsy.
In some embodiments, the individual is a mammal.
In some embodiments, the mammal is a human.
In some embodiments, the human has a body mass index of about 18.5 to about 45. In some
embodiments, the human has a body mass index of about 25 to about 45. In some embodiments, the
human has a body mass index of about 30 to about 45. In some embodiments, the human has a body
mass index of about 35 to about 45.
One aspect of the present invention pertains to methods of producing a pharmaceutical
composition comprising admixing a compound, as described herein, and a pharmaceutically
acceptable carrier.
One aspect of the present invention pertains to methods for the prophylaxis or treatment of
improving memory function, sleeping and arousal, anxiety, depression, mood disorders, seizure,
obesity, diabetes, appetite and eating disorders, cardiovascular disease, hypertension, dyslipidemia,
myocardial infarction, binge eating disorders including bulimia, anorexia, mental disorders including
manic depression, schizophrenia, delirium, dementia, stress, cognitive disorders, attention deficit
disorder, substance abuse disorders and dyskinesias including Parkinson's disease, epilepsy, and
addiction in mammals in need of such treatment comprising administering to the mammal a

294
therapeutically effective amount of a compound, as described herein, or pharmaceutical composition
thereof.
One embodiment of the invention includes any compound of the invention which selectively
binds an MCH receptor, such selective binding is preferably demonstrated by a Ki for one or more
other GPCR(s), preferably NPY, being at least 10-fold greater than the Ki for any particular MCH
receptor, preferable MCHR1.
As used herein, the term "alky!" is intended to denote hydrocarbon compounds including
straight chain and branched chain, including for example but not limited to methyl, ethyl, n-propyl,
isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, tsopentyl, tert-pentyl, n-hexyl, and the like.
The term "alkoxy" is intended to denote substituents of the formula -O-alkyl.
At various places in the present specification substituents of compounds of the invention are
disclosed in groups. It is specifically intended that the invention include each and every individual
subcombination of the members of such groups.
G-protein coupled receptors (GPCRs) represent a major class of cell surface receptors with
which many neurotransmitters interact to mediate their effects. GPCRs are predicted to have seven
membrane-spanning domains and are coupled to their effectors via G-proteins linking receptor
activation with intracellular biochemical sequelae such as stimulation of adenylyl cyclase. Melanin
Concentrating Hormone (MCH), a cyclic peptide, has been identified as the endogenous ligand of the
orphan G-protein coupled receptor SLC-1. See, for example, Shimomura et al., Biochem. Biophys.
Res. Commun. 261, 622-26 (1999). Studies have indicated that MCH acts as a
neurotransmitter/modulator/regulator to alter a number of behavioral responses.
Mammalian MCH (19 amino acids) is highly conserved between rat, mouse, and human,
exhibiting 100% amino acid identity, but its physiological roles are less clear. MCH has been reported
to participate in a variety of processes including feeding, water balance, energy metabolism, general
arousal/attention state, memory and cognitive functions, and psychiatric disorders. For reviews, see
1. Baker, Int. Rev. Cytol. 126:1-47(1991); 2. Baker, TEM 5:120-126 (1994); 3. Nahon, Critical Rev.
inNeurobiol 221:221-262, (1994); 4. Knigge etal., Peptides 18(7):1095-1097, (1996). The role of
MCH in feeding or body weight regulation is supported by Qu et al., Nature 380:243-247, (1996),

295
demonstrating that MCH is over expressed in the hypothalamus of ob/ob mice compared with
ob/+mice, and that fasting further increased MCH mRNA in both obese and normal mice during
fasting. MCH also stimulated feeding in normal rats when injected into the lateral ventricles as
reported by Rossi etal., Endocrinology 138:351-355, (1997). MCH also has been reported to
functionally antagonize the behavioral effects of ct-MSH; see: Miller et al., Peptides 14:1-10, (1993);
Gonzalez et al5 Peptides 17:171-177, (1996); and Sanchez et al., Peptides 18:3933-396, (1997). In
addition, stress has been shown to increase POMC mRNA levels while decreasing the MCH precursor
preproMCH (ppMCH) mRNA levels; Presse et al., Endocrinology 131:1241 -1250, (1992). Thus
MCH can serve as an integrative neuropeptide involved in the reaction to stress, as well as in the
regulation of feeding and sexual activity; Baker, Int. Rev. Cytol. 126:1-47, (1991); Knigge et al.,
Peptides 17:1063-1073,(1996).
The localization and biological activities of MCH peptide suggest that the modulation of
MCH receptor activity can be useful in a number of therapeutic applications. MCH is expressed in the
lateral hypothalamus, a brain area implicated in the regulation of thirst and hunger: Grillon et al.,
Neuropeptides 31:131-136, (1997); recently orexins A and B, which are potent orexigenic agents,
have been shown to have very similar localization to MCH in the lateral hypothalamus; Sakurai et al.,
Cell 92:573-585 (1998). MCH mRNA levels in this brain region are increased in rats after 24 hours
of food-deprivation; Herve and Fellmann, Neurpeptides 31:237-242 (1997); after insulin injection, a
significant increase in the abundance and staining intensity of MCH immunoreactive perikarya and
fibres was observed concurrent with a significant increase in the level of MCH mRNA;
Bahjaoui-Bouhaddi et al., Neuropeptides 24:251-258, (1994). Consistent with the ability of MCH to
stimulate feeding in rats; Rossi et al., Endocrinology 138:351-355, (1997); is the observation that
MCH mRNA levels are upregulated in the hypothalami of obese ob/ob mice; Qu et al., Nature
380:243-247, (1996); and decreased in the hypothalami of rats treated with leptin, whose food intake
and body weight gains are also decreased; Sahu, Endocrinology 139:795-798, (1998). MCH appears
to act as a functional antagonist of the melanocortin system in its effects on food intake and on
hormone secretion within the HPA (hypothalamopituitary/adrenal axis); Ludwig et al., Am. J. Physiol.
Endocrinol. Metab. 274:E627-E633, (1998). Together these data suggest a role for endogenous MCH

296
in the regulation of energy balance and response to stress, and provide a rationale for the development
of specific compounds acting at MCH receptors for use in the treatment of obesity and stress-related
disorders.
Accordingly, a MCH receptor antagonist is desirable for the prophylaxis or treatment of
obesity or obesity related disorders. An obesity related disorder is a disorder that has been directly or
indirectly associated to obesity, such as, type II diabetes, syndrome X, impaired glucose tolerance,
dyslipidaemia, hypertension, coronary heart disease and other cardiovascular disorders including
atherosclerosis, insulin resistance associated with obesity and psoriasis, for treating diabetic
complications and other diseases such as polycystic ovarian syndrome (PCOS), certain renal diseases
including diabetic nephropathy, glomerulonephritis, glomerular sclerosis, nephrotic syndrome,
hypertensive nephrosclerosis, end-stage renal diseases and microalbuminuria as well as certain eating
disorders.
In species studied to date, a major portion of the neurons of the MCH cell group occupies a
rather constant location in those areas of the lateral hypothalamus and subthalamus where they lie and
can be a part of some of the so-called "extrapyramidal" motor circuits. These involve substantial
striato- and pallidofugal pathways involving the thalamus and cerebral cortex, hypothalamic areas,
and reciprocal connections to subthaiamic nucleus, substantia nigra, and mid-brain centers;
Bittencourt et al., J. Comp. Neurol. 319:218-245, (1992). In their location, the MCH cell group may
offer a bridge or mechanism for expressing hypothalamic visceral activity with appropriate and
coordinated motor activity. Clinically it can be of some value to consider the involvement of this
MCH system in movement disorders, such as Parkinson's disease and Huntingdon's Chorea in which
extrapyramidal circuits are known to be involved.
Human genetic linkage studies have located authentic hMCH loci on chromosome 12
(12q23-24) and the variant hMCH loci on chromosome 5 (5qI2-13) (Pedeutour et al., 1994). Locus
12q23-24 coincides with a locus to which autosomal dominant cerebellar ataxia type II (SCA2) has
been mapped; Auburger et al., Cytogenet. Cell. Genet. 61:252-256, (1992); Twells et al., Cytogenet.
Cell. Genet. 61:262-265, (1992). This disease comprises neurodegenerative disorders, including an
olivopontocerebellar atrophy. Furthermore, the gene for Darier's disease, has been mapped to locus

297
12q23-24; Craddock et al., Hum. Mol. Genet. 2:1941-1943, (1993). Dariers' disease is characterized
by abnormalities I keratinocyte adhesion and mental illnesses in some families. In view of the
functional and neuroanatomical patterns of the MCH neural system in the rat and human brains, the
MCH gene can represent a good candidate for SCA2 or Darier's disease. Interestingly, diseases with
high social impact have been mapped to this locus. Indeed, the gene responsible for chronic or acute
forms of spinal muscular atrophies has been assigned to chromosome 5q 12-13 using genetic linkage
analysis; Melki et al., Nature (London) 344:767-768, (1990); Westbrook et al., Cytogenet. Cell. Genet.
61:225-231, (1992). Furthermore, independent lines of evidence support the assignment of a major
schizophrenia locus to chromosome 5ql 1.2-13.3; Sherrington et al., Nature (London) 336:164-3 67,
(1988); Bassett et al, Lancet 1:799-801, (1988); Gilliam et al, Genomics 5:940-944, (1989). The
above studies suggest that MCH can play a role in neurodegenerative diseases and disorders of
emotion.
Additional therapeutic applications for MCH-related compounds are suggested by the
observed effects of MCH in other biological systems. For example, MCH can regulate reproductive
functions in male and female rats. MCH transcripts and MCH peptide were found within germ ceils
in testes of adult rats, suggesting that MCH can participate in stem cell renewal and/or differentiation
of early spermatocytes; Hervieu etal. Biology of Reduction 54:1161-1172, (1996). MCH injected
directly into the medial preoptic area (MPOA) or ventromedial nucleus (VMN) stimulated sexual
activity in female rats; Gonzalez et al., Peptides 17:171-177, (1996). In ovariectomized rats primed
with estradiol, MCH stimulated luteinizing hormone (LH) release while anti-MCH antiserum
inhibited LH release; Gonzalez et al, Neuroendocrinology 66:254-262, (1997). The zona incerta,
which contains a large population of MCH cell bodies, has previously been identified as a regulatory
site for the pre-ovulatory LH surge; MacKenzie et al, Neuroendocrinology 39:289-295, (1984).
MCH has been reported to influence release of pituitary hormones including ACTH and oxytocin.
MCH analogues can also be useful in treating epilepsy. In the PTZ seizure model, injection of MCH
prior to seizure induction prevented seizure activity in both rats and guinea pigs, suggesting that
MCH-containing neurons can participate in the neural circuitry underlying PTZ-induced seizure;
Knigge and Wagner, Peptides 18:1095-1097, (1997). MCH has also been observed to affect

298
behavioral correlates of cognitive functions. MCH treatment hastened extinction of the passive
avoidance response in rats; McBride et al., Peptides 15:757-759, (1994); raising the possibility that
MCH receptor antagonists can be beneficial for memory storage and/or retention. A possible role for
MCH in the modulation or perception of pain is supported by the dense innervation of the
periaqueductal grey (PAG) by MCH-positive fibers. Finally, MCH can participate in the regulation
of fluid intake. ICV infusion of MCH in consC1-5us sheep produced diuretic, natriuretic, and kaliuretic
changes in response to increased plasma volume; Parkes, J. Neuroendocrinol. 8:57-63, (1996).
Together with anatomical data reporting the presence of MCH in fluid regulatory areas of the brain,
the results indicate that MCH can be an important peptide involved in the central control of fluid
homeostasis in mammals.
In a recent citation MCHR1 antagonists surprisingly demonstrated their use as an
anti-depressants and/or anti-anxiety agents. MCHR1 antagonists have been reported to show
antidepressant and anxiolytic activities in rodent models, such as, social interaction, forced swimming
test and ultrasonic vocalization. Therefore, MCHR1 antagonists could be useful to independently
treat subjects with depression and/or anxiety. Also, MCHR1 antagonists could be useful to treat
subjects that suffer from depression and/or anxiety and obesity.
This invention provides a method of treating an abnormality in a subject wherein the
abnormality is alleviated by decreasing the activity of a mammalian MCH1 receptor which comprises
administering to the subject an amount of a compound which is a mammalian MCH1 receptor
antagonist effective to treat the abnormality. In separate embodiments, the abnormality is a regulation
of a steroid or pituitary hormone disorder, an epinephrine release disorder, an anxiety disorder, genta
gastrointestinal disorder, a cardiovascular disorder, an electrolyte balance disorder, hypertension,
diabetes, a respiratory disorder, asthma, a reproductive function disorder, an immune disorder, an
endocrine disorder, a musculoskeletal disorder, a neuroendocrine disorder, a cognitive disorder, a
memory disorder, a sensory modulation and transmission disorder, a motor coordination disorder, a
sensory integration disorder, a motor integration disorder, a dopaminergic function disorder, a sensory
transmission disorder, an olfaction disorder, a sympathetic innervation disorder, an affective disorder,
a stress-related disorder, a fluid-balance disorder, a seizure disorder, pain, psychotic behavior,

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morphine tolerance, opiate addiction or migraine.
Compositions of the invention can conveniently be administered in unit dosage form and can
be prepared by any of the methods well known in the pharmaceutical art, for example, as described in
Remington's Pharmaceutical Sciences (Mack Pub. Co., Easton, PA, 1980).
The compounds of the invention can be employed as the sole active agent in a pharmaceutical
or can be used in combination with other active ingredients which could facilitate the therapeutic
effect of the compound.
Compounds of the present invention or a solvate or physiologically functional derivative
thereof can be used as active ingredients in pharmaceutical compositions, specifically as a MCH
receptor antagonists. By the term "active ingredient" is defined in the context of a "pharmaceutical
composition" and shall mean a component of a pharmaceutical composition that provides the primary
pharmaceutical benefit, as opposed to an "inactive ingredient" which would generally be recognized
as providing no pharmaceutical benefit. The term "pharmaceutical composition" shall mean a
composition comprising at one active ingredient and at least one ingredient that is not an active
ingredient (for example and not limitation, a filler, dye, or a mechanism for slow release), whereby the
composition is amenable to use for a specified, efficaC1-5us outcome in a mammal (for example, and
not limitation, a human).
Pharmaceutical compositions, including, but not limited to, pharmaceutical compositions,
comprising at least one compound of the present invention and/or an acceptable salt or solvate thereof
(e.g., a pharmaceutically acceptable salt or solvate) as an active ingredient combined with at least one
carrier or excipient (e.g., pharmaceutical carrier or excipient) can be used in the treatment of clinical
conditions for which a MCH receptor antagonist is indicated. At least one compound of the present
invention can be combined with the carrier in either solid or liquid form in a unit dose formulation.
The pharmaceutical carrier must be compatible with the other ingredients in the composition and must
be tolerated by the individual recipient. Other physiologically active ingredients can be incorporated
into the pharmaceutical composition of the invention if desired, and if such ingredients are compatible
with the other ingredients in the composition. Formulations can be prepared by any suitable method,
typically by uniformly mixing the active compound(s) with liquids or finely divided solid carriers, or

300
both, in the required proportions, and then, if necessary, forming the resulting mixture into a desired
shape.
Conventional excipients, such as binding agents, fillers, acceptable wetting agents, tabletting
lubricants, and disintegrants can be used in tablets and capsules for oral administration. Liquid
preparations for oral administration can be in the form of solutions, emulsions, aqueous or oily
suspensions, and syrups. Alternatively, the oral preparations can be in the form of dry powder that can
be reconstituted with water or another suitable liquid vehicle before use. Additional additives such as
suspending or emulsifying agents, non-aqueous vehicles (including edible oils), preservatives, and
flavorings and colorants can be added to the liquid preparations. Parenteral dosage forms can be
prepared by dissolving the compound of the invention in a suitable liquid vehicle and filter sterilizing
the solution before filling and sealing an appropriate vial or ampoule. These are just a few examples
of the many appropriate methods well known in the art for preparing dosage forms.
It is noted that when the MCH receptor antagonists are utilized as active ingredients in a
pharmaceutical composition, these are not intended for use only in humans, but in other non-human
mammals as well. Indeed, recent advances in the area of animal health-care mandate that
consideration be given for the use of MCH receptor antagonists for the treatment of obesity in
domestic animals (e.g., cats and dogs), and MCH receptor antagonists in other domestic animals
where no disease or disorder is evident (e.g., food-oriented animals such as cows, chickens, fish, etc.).
Those of ordinary skill in the art are readily credited with understanding the utility of such compounds
m such settings.
Pharmaceutically acceptable salts of the compounds of the invention can be prepared by
reacting the free acid or base forms of these compounds with the appropriate base or acid in water, in
an organic solvent, or in a mixture of the two; generally, nonaqueous media like ether, ethyl acetate,
ethanol, isopropanol, dioxane, or acetonitrile are preferred. For instance, when the compound (I)
possesses an acidic functional group, it can form an inorganic salt such as an alkali metal salt (e.g.,
sodium salt, potassium salt, etc.), an alkaline earth metal salt (e.g. calcium salt, magnesium salt,
barium salt, etc.), and an ammonium salt. When the compound (I) possesses a basic functional group,
it can form an inorganic salt (e.g., hydrochloride, sulfate, phosphate, hydrobromate, etc.) or an organic

301
salt (e.g., acetate, maleate, fumarate, succinate, methanesulfonate, p-toluenesulfonate, citrate, tartrate,
etc.).
Other Utilities
Another object of the present invention relates to radiolabelled compounds of Formula (la)
that would be useful not only in radio-imaging but also in assays, both in vitro and in vivo, for
localizing and quantitating MCH in tissue samples, including human, and for identifying MCH
ligands by inhibition binding of a radiolabetled compound. It is a further object of this invention to
develop novel MCH assays of which comprise such radiolabelled compounds.
Suitable radionuclides that can be incorporated in compounds of the present invention include
but are not limited to 3H (also written as T), nC, I4C, 18F, 1251,82Br, I231,124I, I25I, 1311,75Br, 76Br, 15O,
13N, j5S and 77Br. The radionuchde that is incorporated in the instant radiolabelled compounds will
depend on the specific application of that radiolabelled compound. Thus, for in vitro MCH labeling
and competition assays, compounds that incorporate 3H, 14C, 125I, I311,35S or 82Br will generally be
most useful. For radio-imaging applications UC, l8F, 125I, n\ 1241,13lI,75Br, 76Br or 77Br will generally
be most useful.
It is understood that a "radio-labelled " or "labelled compound" is a compound of Formula
(la) that has incorporated at least one radionuclide; in some embodiments the radionuclide is selected
from the group consisting of 3H, 14C, 1251,35S and 82Br; in some embodiments the radionuclide 3H or
14C. Moreover, it should be understood that all of the atoms represented in the compounds of the
invention can be either the most commonly occurring isotope of such atoms or the more scarce
radio-isotope or nonradio-active isotope.
Synthetic methods for incorporating radio-isotopes into organic compounds including those
applicable to those compounds of the invention are well known in the art and include incorporating
activity levels of tritium into target molecules include: A. Catalytic Reduction with Tritium Gas -
This procedure normally yields high specific activity products and requires halogenated or unsaturated
precursors. B. Reduction with Sodium Borohydride [ H] - This procedure is rather inexpensive and
requires precursors containing reducible functional groups such as aldehydes, ketones, lactones, esters,

302
and the like. C. Reduction with Lithium Aluminum Hydride [JH ] - This procedure offers products
at almost theoretical specific activities. It also requires precursors containing reducible functional
groups such as aldehydes, ketones, Iactones, esters, and the like. D. Tritium Gas Exposure Labeling
- This procedure involves exposing precursors containing exchangeable protons to tritium gas in the
presence of a suitable catalyst. E. N-Methylation using Methyl Iodide [3H] - This procedure is
usually employed to prepare O-methyl or N-methyl (3H) products by treating appropriate precursors
with high specific activity methyl iodide (JH). This method in general allows for high specific activity,
such as about 80-87 Ci/mmol.
Synthetic methods for incorporating activity levels of I25I into target molecules include: A.
Sandmeyer and like reactions - This procedure transforms an aryl or heteroaryl amine into a
diazonium salt, such as a tetrafluoroborate salt, and subsequently to 125I labelled compound using
Na125I. A represented procedure was reported by Zhu, D.-G. and co-workers in J. Org. Chem. 2002,
67,943-948. B. Ortho " Iodination of phenols -This procedure allows for the incorporation of !25I
at the ortho position of a phenol as reported by Collier, T. L. and co-workers in J. Labelled Compd
Radiopharm. 1999, 42, S264-S266. C. Aryl and heteroaryl bromide exchange with l25I - This
method is generally a two step process. The first step is the conversion of the aryl or heteroaryl
bromide to the corresponding tri-alkyltin intermediate using for example, a Pd catalyzed reaction [i.e.
Pd(Ph3P)4] or through an aryl or heteroaryl lithium, in the presence of a tri-alkyltinhalide or
hexaalkylditin [e.g., (CH3)3SnSn(CH3)3]. A represented procedure was reported by Bas, M.-D. and
co-workers in J. Labelled Compd Radiopharm. 2001, 44, S280-S282.
A radiolabelled MCH compound of Formula (I) can be used in a screening assay to
identify/evaluate compounds. In general terms, a newly synthesized or identified compound (i.e., test
compound) can be evaluated for its ability to reduce binding of the "radiolabelled compound of
Formula (la)" to the MCH receptor. Accordingly, the ability of a test compound to compete with the
"radio-labelled compound of Formula (la)" for the binding to the MCH receptor directly correlates to
its binding affinity.
The labelled compounds of the present invention bind to the MCH receptor. In one
embodiment the labelled compound has an IC50 less than about 500 \\M, in another embodiment the

303
labelled compound has an IC50 less than about 100 |_iM, in yet another embodiment the labelled
compound has an IC50 less than about 10 (iM, in yet another embodiment the labelled compound has
an IC5o less than about 1 jaM, and in still yet another embodiment the labelled inhibitor has an IC50 less
than about 0.1 fiM.
Preparation of Compound of Formula (I) - General synthetic methods
The novel substituted quinolines, tetrahydroquinazolines, and pyrimidines of the present
invention can be readily prepared according to a variety of synthetic manipulations, all of which would
be familiar to one skilled in the art. Preferred methods for the preparation of compounds of the present
invention include, but are not limited to, those described in Scheme 1-24.
The common intermediate (F) of the novel substituted quinolines can be prepared as shown in
Scheme 1. Commercially available 2,4-dihydroxyquinoline (A), wherein T and p is as defined above,
is converted to 2,4-dihaIo-quinoIine (B) by a halogenating agent with or without a base (wherein X is
halogen such as chloro, bromo, or iodo). The halogenating agent includes phosphorous oxychloride
(POCI3), phosphorous oxybromide (POBr3), or phosphorus pentachloride (PC15). The base includes
a tertiary amine (preferably Af,iV-diisopropyIethylamine, etc.) or an aromatic amine (preferably
AyV-dimethylaniline, etc.). Reaction temperature ranges from about 100°C to 200°C, preferably about
140°Ctol80°C.
The halogen of 4-position of 2,4-dihalo-quinoIine (B) is selectively substituted by a primary
or secondary amine (HNR2aR2b, wherein R2a and R2b are as defined above) with or without a base in
an inert solvent to provide the corresponding 4-substitued amino adduct (C). The base includes an
alkali metal carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydroxide (preferably sodium hydroxide, etc.), or a tertiary amine (preferably
AyV-diisopropylethylamine, triethylamine, or JV-methylmorpholine, etc.). The inert solvent includes
lower alkyl alcohol solvents (preferably methanoi, ethanol, 2-propanol, or butanol, etc.), ethereal
solvents (preferably tetrahydrofuran or dioxane, etc.), or amide solvents (preferably
AyV-dim ethyl form amide or l-methyl-pyrrolidin-2-one, etc.). Reaction temperature ranges from about
0°C to 200°C, preferably about 10°C to 150°C.

304
In turn, this is substituted by the mono-protected diamine (D), wherein R3, R4, A, and B are
as defined above and P is a protective group, with or without a base in an inert solvent to provide
2,4-disubstituted amino quinoline (E). The base includes an alkali metal carbonate (preferably
sodium carbonate or potassium carbonate, etc.), an alkali metal hydroxide (preferably sodium
hydroxide, etc.), or a tertiary amine (preferably A^^-diisopropylethylamine, triethylamine, or
TV-methylmorpholine, etc.). The inert solvent includes lower alkyl alcohol solvents (preferably
methanol, ethanol, 2-propanol, or butanol, etc.) or amide solvents (preferably
AyV-dimethylformamide or I-methyl-pyrrolidin-2-one, etc.). Reaction temperature ranges from about
50°C to 200°C, preferably about 80°C to 150°C. Also this reaction can be carried out under microwave
conditions.
Representative protecting groups suitable for a wide variety of synthetic transformations are
disclosed in Greene and Wuts, Protective Groups in Organic Synthesis, second edition, John Wiley
& Sons, New York, 1991, the disclosure of which is incorporated herein by reference in its entirety.
The deprotection of the protective group leads to the common intermediate (F) of the novel substituted
quinolines.

305

The conversion of the common intermediate (F) to the novel substituted quinolines (G-K) of
the present invention is outlined in Scheme 2.
The amine (F) is reacted with a carboxylic acid (R4CO2H) and a dehydrating condensing
agent in an inert solvent with or without a base to provide the novei amide (G) of the present invention.
The dehydrating condensing agent includes dicyclohexylcarbodiimide (DCC),
l-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDOHC1),
bromo-tris-pyrroiidino-phosnium hexafluorophosphate (PyBroP),
O-(7-azabenzotriazoI-I-yl)-l,I,3,3-tetramethyluronium hexafluorophosphate (HATU), or
l-cyclohexyl-3-methylpoIystyrene-carbodiimide. The base includes a tertiary amine (preferably
ACAf-diisopropylethylamine or triethylamine, etc.). The inert solvent includes lower halocarbon
solvents (preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents
(preferably tetrahydrofuran or dioxane), nitrile solvents (preferably acetonitrile, etc.), or amide
solvents (preferably AyV-dimethylformamide, etc.). In case of need, 1-hydroxybenzotriazole (HOBT),

306
HOBT-6-carboxaamidomethyl polystyrene, or 1 -hydroxy-7-azabenzotriazoie (HOAT) can be used as
a reactant agent. Reaction temperature ranges from about -20cC to 50°C, preferably about 0°C to
40°C.
Alternatively, the novel amide (G) of the present invention can be obtained by amidation
reaction using an acid chloride (RjCOCl) and a base in an inert solvent. The base includes an alkali
metal carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogencarbonate (preferably sodium hydrogencarbonate or potassium hydrogencarbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably Af,7V-diisopropylethylamine, triethylamine, or ./V-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine, imidazole, poly-(4-vinylpyridine), etc.). The inert solvent includes lower
halocarbon solvents (preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal
solvents (preferably tetrahydrofuran or dioxane), amide solvents (preferably Ayy-dimethylformamide,
etc.), or aromatic solvents (preferably toluene or pyridine, etc.). Reaction temperature ranges from
about -20°C to 50°C, preferably about 0DC to 40°C.
The novel amide (G) of the present invention is reacted with a reducing agent in an inert
solvent to provide the novel amine (H) of the present invention. The reducing agent includes alkali
metal aluminum hydrides (preferably lithium aluminum hydride), alkali metal borohydrides
(preferably lithium borohydride), alkali metal trialkoxyaluminum hydrides (preferably lithium
tri-ter/-butoxyaluminum hydride), dialkylaluminum hydrides (preferably di-isobutylaluminum
hydride), borane, dialkylboranes (preferably di-isoamyl borane), alkali metal trialkylboron hydrides
(preferably lithium triethylboron hydride). The inert solvent includes ethereal solvents (preferably
tetrahydrofuran or dioxane) or aromatic solvents (preferably toluene, etc.). Reaction temperature
ranges from about -78°C to 200°C, preferably about 50°C to 120°C.
Alternatively, the novel amine (H) of the present invention can be obtained by reductive
animation reaction using aldehyde (RjCHO) and a reducing agent in an inert solvent with or without
an acid. The reducing agent includes sodium triacetoxyborohydride, sodium cyanoborohydride,
sodium borohydride, or boran-pyridine complex, preferably sodium triacetoxyborohydride or sodium
cyanoborohydride. The inert solvent includes lower alkyl alcohol solvents (preferably methanol or

307
ethanol, etc.), lower halocarbon solvents (preferably dichloromethane, dichloroethane, or chloroform,
etc.), ethereal solvents (preferably tetrahydrofuran or dioxane), or aromatic solvents (preferably
toluene, etc.)- The acid includes an inorganic acid (preferably hydrochloric acid or sulfuric acid) or
an organic acid (preferably acetic acid). Reaction temperature ranges from about -20°C to 120°C,
preferably about 0°C to 100°C. Also this reaction can be carried out under microwave conditions.
The novel urea (I) of the present invention can be obtained by urea reaction using an
isocyanate (RjNCO) in an inert solvent with or without a base. The base includes an alkali metal
carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogencarbonate (preferably sodium hydrogencarbonate or potassium hydrogencarbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably AyV-diisopropylethyl amine, triethylamine, or A^-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine or imidazole, etc.). The inert solvent includes lower halocarbon solvents
(preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably
tetrahydrofuran or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or polar solvents
(preferably A^N-dirnethylformamide or dimethyl sulfoxide, etc.). Reaction temperature ranges from
about -20°C to 120°C, preferably about 0°C to 100°C.
The amine (F) is reacted with a isothiocyanate (RiNCS) in an inert solvent with or without a
base to provide the novel thiourea (J) of the present invention. The base includes an alkali metal
carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogencarbonate (preferably sodium hydrogencarbonate or potassium hydrogencarbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably TVyV-diisopropylethylamine, triethylamine, or iV-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine or imidazole, etc.). The inert solvent includes lower halocarbon solvents
(preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably
tetrahydrofuran or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or amide solvents
(preferably AyV-dimethylformamide, etc.). Reaction temperature ranges from about -20°C to 120°C,
preferably about 0°C to 100°C.
The novel urethane (K) of the present invention can be obtained by urethane reaction using

308
RiOCOX, wherein X is halogen such as chloro, bromo, or iodo, in an inert solvent with or without a
base. The base includes an alkali metal carbonate (preferably sodium carbonate or potassium
carbonate, etc.), an alkali metal hydrogen carbonate (preferably sodium hydrogencarbonate or
potassium hydrogencarbonate, etc.), an alkali hydroxide (preferably sodium hydroxide or potassium
hydroxide, etc.), a tertiary amine (preferably A^V-diisopropylethylamine, triethylamine, or
iV-methylmorpholine, etc.), or an aromatic amine (preferably pyridine, imidazole, or
poly-(4-vinylpyridine), etc.). The inert solvent includes lower halocarbon solvents (preferably
dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably tetrahydrofiiran
or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or polar solvents (preferably
A^V-dimethylformamide or dimethyl sulfoxide, etc.). Reaction temperature ranges from about -20°C
to 120°C, preferably about 0°C to 100°C.

309

Compounds of Formula (N) can be prepared as shown in Scheme 3.
[4-(BenzyIoxycarbonylamino-methyI)-cyclohexyI]-carbamic acid tert-butyl ester (L) is synthesized by
the method which is described in WO 01/72710. The deprotection of Boc-group is achieved by an
acid to give the amine (M). The coupling of the amine with quinoline core (C), which is synthesized
as scheme 1, gives 2,4-disubstituted amino quinoline. The deprotection of Z-group is achieved by
hydrogen reduction to give compounds of Formula (N).

310

Compounds of Formula (P) can be prepared as shown in Scheme 4. The dicarboxylic acid of
commercially available c/s-cyclohexane-l,4-dicarboxylic acid is transformed to dibenzyl carbamate
by curtius rearrangement. The deprotection of Z-group is achieved by hydrogen reduction to give the
diamine. The mono-protection of the diamine can be achieved by the method described in Synthetic
communications, 20, 2559-2564 (1990) to give the compound (O). The coupling of the amine with
quinoline core (C), which is synthesized as scheme 1, gives 2,4-disubstituted amino quinoiine. The
deprotection of Boc-group is achieved by an acid to give the amine (P).

311

The common intermediate (V) of the novel substituted tetrahydroquinazolines can be
prepared as shown in Scheme 5. Commercially available ethyl 2-cyclohexanonecarboxylate (Q) ,
wherein T and p is as defined above, is transformed to 2,4-dihydroxytetrahydroquinazoline (R)
according to the method described in EP 0604920. 2,4-Dihydroxytetrahydroquinazoline (R) is
converted to 2,4-dihalo-tetrahydroquinazoline (S) by a halogenating agent with or without a base
(wherein X is halogen such as chloro, bromo, or iodo). The halogenating agent includes phosphorous
oxychloride (POC13), phosphorous oxybromide (POBr3), or phosphorus pentachloride (PC15). The
base includes a tertiary amine (preferably JV/Z-diisopropylethylamine, etc.) or an aromatic amine
(preferably AyV-dimethylaniline, etc.). Reaction temperature ranges from about 100°C to 200°C,
preferably about 140°C to 180°C.
The halogen of 4-position of 2,4-dihalo-tetrahydroquinazoline (S) is selectively substituted by
a primary or secondary amine (HNR2aR2b, wherein R2a and R2b are as defined above) with or without
a base in an inert solvent to provide the corresponding 4-substitued amino adduct (T). The base
includes an alkali metal carbonate (preferably sodium carbonate or potassium carbonate, etc.), an
alkali metal hydroxide (preferably sodium hydroxide, etc.), or a tertiary amine (preferably
7^^V-diisopropyIethylamine? triethylamine, or A^methylmorpholine, etc.). The inert solvent includes
lower alkyl alcohol solvents (preferably methanol, ethanol, 2-propanol, or butanol, etc.), ethereal
solvents (preferably tetrahydrofuran or dioxane, etc.), or amide solvents (preferably

312
AyV-dimethylformamide or l-methyI-pyrrolidin-2-one, etc.). Reaction temperature ranges from about
0°C to 200°C, preferably about 10°C to I50°C.
In turn, this is substituted by the mono-protected diamine (D) , wherein R3, R4, A, and B are
as defined above and P is a protective group, with or without a base in an inert solvent to provide
2,4-disubstituted amino tetrahydroquinazoline (U). The base includes an alkali meta! carbonate
(preferably sodium carbonate or potassium carbonate, etc.), an alkali metal hydroxide (preferably
sodium hydroxide, etc.), or a tertiary amine (preferably AyV-diisopropylethylamine, triethylamine, or
yV-methylmorpholine, etc.). The inert solvent includes lower alkyl alcohol solvents (preferably
methanol, ethanol, 2-propanol, or butanol, etc.) or amide solvents (preferably
Ay^-dimethylformamide or l-methyl-pyrrolidin-2-one, etc.). Reaction temperature ranges from about
50°C to 200°C, preferably about 80°C to 150°C. Also this reaction can be carried out under microwave
conditions.
The deprotection of the protective group leads to the common intermediate (V) of the novel
substituted tetrahydroquinazolines.


-Ill
The conversion of the common intermediate (V) to the novel substituted
tetrahydroquinazolines (W-A') of the present invention is outlined in Scheme 6.
The amine (V) is reacted with a carboxylic acid (RiCO2H) and a dehydrating condensing
agent in an inert solvent with or without a base to provide the novel amide (W) of the present invention.
The dehydrating condensing agent includes dicyclohexylcarbodiimide (DCC),
l-ethyI-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDOHC1),
bromo-tris-pyrrolidino-phosnium hexafluorophosphate (PyBroP),
0-(7-azabenzotriazol-l-yI)-l,l,3,3-tetrarnethyIuronium hexafluorophosphate (HATU), or
l-cyclohexyl-3-methylpoIystyrene-carbodiimide. The base includes a tertiary amine (preferably
Af,JV-diisopropylethylamine or triethylamine, etc.). The inert solvent includes lower halocarbon
solvents (preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents
(preferably tetrahydrofuran or dioxane), nitrile solvents (preferably acetonitrile, etc.), or amide
solvents (preferably A^-dimethylform amide, etc.). In case of need, 1 -hydroxybenzotriazole (HOBT),
HOBT-6-carboxaamidomethyl polystyrene, or l-hydroxy-7-azabenzotriazole (HOAT) can be used as
a reactant agent. Reaction temperature ranges from about -20°C to 50°C, preferably about 0°C to
40°C.
Alternatively, the novel amide (W) of the present invention can be obtained by amidation
reaction using an acid chloride (RiCOCI) and a base in an inert solvent. The base includes an alkali
metal carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogencarbonate (preferably sodium hydrogencarbonate or potassium hydrogencarbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably iV,iV-diisopropylethylamme, triethylamine, or iV-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine, imidazole, poly-(4-vinylpyridine), etc.). The inert solvent includes lower
halocarbon solvents (preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal
solvents (preferably tetrahydrofuran or dioxane), amide solvents (preferably iVJV-dimethylformamide,
etc.), or aromatic solvents (preferably toluene or pyridine, etc.). Reaction temperature ranges from
about -20°C to 50°C, preferably about 0°C to 40°C.

314
The novel amide (W) of the present invention is reacted with a reducing agent in an inert
solvent to provide the novel amine (X) of the present invention. The reducing agent includes alkali
metal aluminum hydrides (preferably lithium aluminum hydride), alkali metal borohydrides
(preferably lithium borohydride), alkali metal trialkoxyaluminum hydrides (preferably lithium
tri-terf-butoxyaluminum hydride), diaikylaluminum hydrides (preferably di-isobutylaluminum
hydride), borane, dialkylboranes (preferably di-isoamyl borane), alkali metal trialkylboron hydrides
(preferably lithium triethylboron hydride). The inert solvent includes ethereal solvents (preferably
tetrahydrofuran or dioxane) or aromatic solvents (preferably toluene, etc.). Reaction temperature
ranges from about -78°C to 200°C, preferably about 50°C to 120°C.
Alternatively, the novel amine (X) of the present invention can be obtained by reductive
animation reaction using aldehyde (RjCHO) and a reducing agent in an inert solvent with or without
an acid. The reducing agent includes sodium triacetoxyborohydride, sodium cyanoborohydride,
sodium borohydride, or boran-pyridine complex, preferably sodium triacetoxyborohydride or sodium
cyanoborohydride. The inert solvent includes lower alkyl alcohol solvents (preferably methanol or
ethanol, etc.), lower halocarbon solvents (preferably dichloromethane, dichloroethane, or chloroform,
etc.), ethereal solvents (preferably tetrahydroforan or dioxane), or aromatic solvents (preferably
toluene, etc.). The acid includes an inorganic acid (preferably hydrochloric acid or sulfuric acid) or
an organic acid (preferably acetic acid). Reaction temperature ranges from about -20°C to 120°C,
preferably about 0°C to 100°C. Also this reaction can be carried out under microwave conditions.
The novel urea (Y) of the present invention can be obtained by urea reaction using an
isocyanate (R]NCO) in an inert solvent with or without a base. The base includes an alkali metal
carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogencarbonate (preferably sodium hydrogencarbonate or potassium hydrogencarbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably AyV-diisopropylethylamine, triethylamine, orTV-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine or imidazole, etc.). The inert solvent includes lower halocarbon solvents
(preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably
tetrahydrofuran or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or polar solvents

315
(preferably 7VyV-dimethylformamide or dimethyl sulfoxide, etc.). Reaction temperature ranges from
about -20°C to 120°C, preferably about 0°C to 100°C.
The amine (V) is reacted with a isothiocyanate (R|NCS) in an inert solvent with or without a
base to provide the novel thiourea (Z) of the present invention. The base includes an alkali metal
carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogencarbonate (preferably sodium hydrogencarbonate or potassium hydrogen carbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably TVyV-diisopropylethylamine, triethylamine, or jV-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine or imidazole, etc.). The inert solvent includes lower halocarbon solvents
(preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably
tetrahydrofuran or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or amide solvents
(preferably AyV-dimethylformamide, etc.). Reaction temperature ranges from about -20°C to 120°C,
preferably about 0°C to 100°C.
The novel urethane (A') of the present invention can be obtained by urethane reaction using
RiOCOX, wherein X is halogen such as chloro, bromo, or iodo, in an inert solvent with or without a
base. The base includes an alkali metal carbonate (preferably sodium carbonate or potassium
carbonate, etc.), an alkali metal hydrogencarbonate (preferably sodium hydrogencarbonate or
potassium hydrogencarbonate, etc.), an alkali hydroxide (preferably sodium hydroxide or potassium
hydroxide, etc.), a tertiary amine (preferably AyV-diisopropylethylamine, triethylamine, or
jV-methylmorpholine, etc.), or an aromatic amine (preferably pyridine, imidazole, or
poly-(4-vinylpyridine), etc.). The inert solvent includes lower halocarbon solvents (preferably
dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably tetrahydrofuran
or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or polar solvents (preferably
AyV-dimethylformamide or dimethyl sutfoxide, etc.). Reaction temperature ranges from about -20°C
to 120°C, preferably about 0°C to 100°C.

316

Compounds of Formula (B') can be prepared as shown in Scheme 7. The coupling of the
amine (M), which is synthesized as scheme 3, with tetrahydroquinazoline core (T), which is
synthesized as scheme 5, gives 2r4-disubstituted amino tetrahydroquinazoline. The deprotection of
Z-group is achieved by hydrogen reduction to give compounds of Formula (B').

317

Compounds of Formula (C) can be prepared as shown in Scheme 8. The coupling of the
amine (O), which is synthesized as scheme 4, with tetrahydroquinazoline core (T), which is
synthesized as scheme 5, gives 2?4-disubstituted amino tetrahydroquinazoline. The deprotection of
Boc-group is achieved by an acid to give the amine (C).

The common intermediate (H') of the novel substituted pyrimidines can be prepared as shown
in Scheme 9. Commercially available substituted uracil (D') , wherein T and p is as defined above, is
converted to substituted 2,4-dihaIo- pyrimidines (E') by a halogenating agent with or without a base
(wherein X is halogen such as chloro, bromo, or iodo). The halogenating agent includes phosphorous
oxychloride (POCI3), phosphorous oxybromide (POBr3), or phosphorus pentachloride (PC15). The

318
base includes a tertiary amine (preferably TVyV-diisopropylethylamine, etc.) or an aromatic amine
(preferably AyV-dimethylaniline, etc.)- Reaction temperature ranges from about 100°C to 200°C,
preferably about 140°C to 180°C.
The halogen of 4-position of substituted 2,4-dihalo-pyrimidines (E') is selectively substituted
by a primary or secondary amine (HNR^Rzb, wherein R2a and R2b are as defined above) with or
without a base in an inert solvent to provide the corresponding 4-substitued amino adduct (F'). The
base includes an alkali metal carbonate (preferably sodium carbonate or potassium carbonate, etc.), an
alkali metal hydroxide (preferably sodium hydroxide, etc.), or a tertiary amine (preferably
A^iV-diisopropylethylamine, triethylamine, orTV-methylmorpholine, etc.). The inert solvent includes
lower alkyl alcohol solvents (preferably methanol, ethanol, 2-propanol, or butanol, etc.), ethereal
solvents (preferably tetrahydrofuran or dioxane, etc.), or amide solvents (preferably
AyV-dimethylformamide or l-methyl-pyrrolidin-2-one, etc.). Reaction temperature ranges from about
0°C to 200°C, preferably about 10°C to 150°C.
In turn, this is substituted by the mono-protected diamine (D), wherein R3, R4, A, and B are
as defined above and P is a protective group, with or without a base in an inert solvent to provide
2,4-disubstituted amino pyrimidines (C). The base includes an alkali metal carbonate (preferably
sodium carbonate or potassium carbonate, etc.), an alkali metal hydroxide (preferably sodium
hydroxide, etc.), or a tertiary amine (preferably AyV-diisopropylethylamine, triethylamine, or
jV-methylmorphoIine, etc.). The inert solvent includes lower alkyl alcohol solvents (preferably
methanol, ethanol, 2-propanol, or butanol, etc.) or amide solvents (preferably
AyV-dimethylformamide or l-methyl-pyrrolidin-2-one, etc.). Reaction temperature ranges from about
50°C to 200°C, preferably about 80°C to 150°C. Also this reaction can be carried out under microwave
conditions.
The deprotection of the protective group leads to the common intermediate (H') of the novel
substituted pyrimidines.

319

The conversion of the common intermediate (H') to the novel substituted pyrimidines fl'-M')
of the present invention is outlined in Scheme 10.
The amine (H') is reacted with a carboxylic acid (RjCC^H) and a dehydrating condensing
agent in an inert solvent with or without a base to provide the novel amide (I') of the present invention.
The dehydrating condensing agent includes dicyclohexylcarbodiimide (DCC),
l-ethyI-3-(3-dimethyIaminopropyl)carbodiimidehydrochloride(EDC*HCl),
bromo-tris-pyrrolidino-phosnium hexafluorophosphate (PyBroP),
0-(7-azabenzotriazoI-l-yl)-l,l,3,3-tetramethyluronium hexafluorophosphate (HATU), or
l-cyclohexyI-3-methylpolystyrene-carbodiimide. The base includes a tertiary amine (preferably
AyV-diisopropylethylamine or triethylamine, etc.). The inert solvent includes lower halocarbon
solvents (preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents
(preferably tetrahydrofuran or dioxane), nitrile solvents (preferably acetonitrile, etc.), or amide
solvents (preferably A^-dimethylformamide, etc.). In case of need, 1 -hydroxybenzotriazole (HOBT),

320
HOBT-6-carboxaamidomethyl polystyrene, or l-hydroxy-7-azabenzotriazole (HOAT) can be used as
a reactant agent. Reaction temperature ranges from about -20°C to 50°C, preferably about 0°C to
40°C.
Alternatively, the novel amide (F) of the present invention can be obtained by amidation
reaction using an acid chloride (RiCOCI) and a base in an inert solvent. The base includes an alkali
metal carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogencarbonate (preferably sodium hydrogen carbonate or potassium hydrogencarbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably AyV-diisopropylethylamine, triethylamine, or TV-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine, imidazole, poly-(4-vinylpyridine), etc.). The inert solvent includes lower
halocarbon solvents (preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal
solvents (preferably tetrahydrofuran or dioxane), amide solvents (preferably TVyV-dimethylformamide,
etc.), or aromatic solvents (preferably toluene or pyridine, etc.). Reaction temperature ranges from
about -20°C to 50°C, preferably about 0°C to 40°C.
The novel amide (V) of the present invention is reacted with a reducing agent in an inert
solvent to provide the novel amine (J') of the present invention. The reducing agent includes alkali
metal aluminum hydrides (preferably lithium aluminum hydride), alkali metai borohydrides
(preferably lithium borohydride), alkali metal trialkoxyaluminum hydrides (preferably lithium
tri-terf-butoxyaluminum hydride), dialkylaluminum hydrides (preferably di-isobutylaluminum
hydride), borane, dialkylboranes (preferably di-isoamyl borane), alkali metal trialkylboron hydrides
(preferably lithium triethylboron hydride). The inert solvent includes ethereal solvents (preferably
tetrahydrofuran or dioxane) or aromatic solvents (preferably toluene, etc.). Reaction temperature
ranges from about -78°C to 200°C, preferably about 50°C to 120°C.
Alternatively, the novel amine (J') of the present invention can be obtained by reductive
amination reaction using aldehyde (RiCHO) and a reducing agent in an inert solvent with or without
an acid. The reducing agent includes sodium triacetoxyborohydride, sodium cyanoborohydride,
sodium borohydride, or boran-pyridine complex, preferably sodium triacetoxyborohydride or sodium
cyanoborohydride. The inert solvent includes lower alkyl alcohol solvents (preferably methanol or

321
ethanol, etc.), lower halocarbon solvents (preferably dichloromethane, dichloroethane, or chloroform,
etc.), ethereal solvents (preferably tetrahydrofuran or dioxane), or aromatic solvents (preferably
toluene, etc.). The acid includes an inorganic acid (preferably hydrochloric acid or sulfuric acid) or
an organic acid (preferably acetic acid). Reaction temperature ranges from about -20°C to 120°C,
preferably about 0°C to 100°C. Also this reaction can be carried out under microwave conditions.
The novel urea (K') of the present invention can be obtained by urea reaction using an
isocyanate (RiNCO) in an inert solvent with or without a base. The base includes an alkali metal
carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogencarbonate (preferably sodium hydrogencarbonate or potassium hydrogencarbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably iYjV-diisopropylethylamine, triethylamine, or jV-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine or imidazole, etc.). The inert solvent includes lower halocarbon solvents
(preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably
tetrahydrofuran or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or polar solvents
(preferably iV^V-dimethylformamide or dimethyl sulfoxide, etc.). Reaction temperature ranges from
about -20°C to 120°C, preferably about 0°C to 100°C.
The amine (H') is reacted with a isothiocyanate (RtNCS) in an inert solvent with or without
a base to provide the novel thiourea (L') of the present invention. The base includes an alkali metal
carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogencarbonate (preferably sodium hydrogencarbonate or potassium hydrogencarbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably A^JV-diisopropylethylamine, triethylamine, or TV-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine or imidazole, etc.). The inert solvent includes lower halocarbon solvents
(preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably
tetrahydrofuran or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or amide solvents
(preferably Af,iV-dimethylformamide, etc.). Reaction temperature ranges from about -20°C to 120°C,
preferably about 0°C to 100°C.
The novel urethane (M') of the present invention can be obtained by urethane reaction using

322
RiOCOCl, wherein X is halogen such as chloro, bromo, or iodo, in an inert solvent with or without a
base. The base includes an alkali metal carbonate (preferably sodium carbonate or potassium
carbonate, etc.), an alkali metal hydrogencarbonate (preferably sodium hydrogencarbonate or
potassium hydrogencarbonate, etc.), an alkali hydroxide (preferably sodium hydroxide or potassium
hydroxide, etc.), a tertiary amine (preferably A^-diisopropylethylamine, triethylamine, or
JV-methylmorpholine, etc.), or an aromatic amine (preferably pyridine, imidazole, or
poly-(4-vinylpyridine), etc.). The inert solvent includes lower halocarbon solvents (preferably
dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably tetrahydrofuran
or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or polar solvents (preferably
AyV-dimethylformamide or dimethyl sulfoxide, etc.). Reaction temperature ranges from about -20°C
to 120°C, preferably about 0°C to 100°C.

JZJ

Compounds of Formula (N') can be prepared as shown in Scheme 11. The coupling of the
amine (M), which is synthesized as scheme 3, with pyrimidine core (F'), which is synthesized as
scheme 9, gives 2,4-disubstituted amino pyrimidine. The deprotection of Z-group is achieved by
hydrogen reduction to give compounds of Formula (N').

324

Compounds of Formula (O') can be prepared as shown in Scheme 12. The coupling of the
amine (O), which is synthesized as scheme 4, with pyrimidine core (F'), which is synthesized as
scheme 9, gives 2,4-disubstituted amino pyrimidine. The deprotection of Boc-group is achieved by

an acid to give the amine (O').
The common intermediate (S') of the novel substituted quinolines can be prepared as shown
in Scheme 13. Commercially available substituted 2-hydroxy-quinoline (P'), wherein R2, T, and p is

325
as defined above, is converted to 2-halo-qumoIines (Q') by a halogenating agent with or without a
base (wherein X is halogen such as chloro, bromo, or iodo). The halogenating agent includes
phosphorous oxychloride (POCI3), phosphorous oxybromide (POBr3), or phosphorus pentachloride
(PCI5). The base includes a tertiary amine (preferably JV,jV-diisopropylethylamine; etc.) or an aromatic
amine (preferably iVyV-dimethylaniline, etc.). Reaction temperature ranges from about 100°C to
200°C, preferably about 140°C to 180°C.
The halide (Q') is substituted by the mono-protected diamine (D), wherein R3, R4, A, and B
are as defined above and P is a protective group, with or without a base in an inert solvent to provide
2-substituted amino quinoline (R'). The base includes an alkali metal carbonate (preferably sodium
carbonate or potassium carbonate, etc.), an alkali metal hydroxide (preferably sodium hydroxide, etc.),
or a tertiary amine (preferably AyV-diisopropylethylamine, triethylamine, or A^methylmorpholine,
etc.)- The inert solvent includes lower alkyl alcohol solvents (preferably methanol, ethanol,
2-propanol, or butanol, etc.) or amide solvents (preferably AyV-dimethylformamide or
l-methyl-pyrrolidin-2-one, etc.). Reaction temperature ranges from about 50°C to 200°C, preferably
about 80°C to 150°C. Also this reaction can be carried out under microwave conditions.
The deprotection of the protective group leads to the common intermediate (S') of the novel
substituted quinolines.


326
The conversion of the common intermediate (S') to the novel substituted quinolines (T'-X')
of the present invention is outlined in Scheme 14.
The amine (S') is reacted with a carboxylic acid (R]CO?H) and a dehydrating condensing
agent in an inert solvent with or without a base to provide the novel amide (T') of the present invention.
The dehydrating condensing agent includes dicyclohexylcarbodiimide (DCC),
l-ethyl-3-(3-dimethyiaminopropyl)carbodiimidehydrochloride (EDOHCI),
bromo-tris-pyrrolidino-phosnium hexafluorophosphate (PyBroP),
O-(7-azabenzotriazol-l-yl)-l,l,3,3-tetramethyluronium hexafluorophosphate (HATU), or
l-cyclohexyl-3-methylpolystyrene-carbodiimide. The base includes a tertiary amine (preferably
A^TV-diisopropylethyfamine or triethylamine, etc.)- The inert solvent includes lower halocarbon
solvents (preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents
(preferably tetrahydrofuran or dioxane), nitrile solvents (preferably acetonitrile, etc.), or amide
solvents (preferably AyV-dirn ethyl formamide, etc.). In case of need, 1-hydroxybenzotriazole (HOBT),
HOBT-6-carboxaamidomethyl polystyrene, or l-hydroxy-7-azabenzotriazole (HOAT) can be used as
a reactant agent. Reaction temperature ranges from about -20°C to 50°C, preferably about 0°C to
40°C.
Alternatively, the novel amide (T') of the present invention can be obtained by amidation
reaction using an acid chloride (RiCOCl) and a base in an inert solvent. The base includes an alkali
metal carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogencarbonate (preferably sodium hydrogencarbonate or potassium hydrogencarbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably A^-diisopropylethylamine, triethylamine, or W-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine, imidazole, poly-(4-vinylpyridine), etc.). The inert solvent includes lower
halocarbon solvents (preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal
solvents (preferably tetrahydrofuran or dioxane), amide solvents (preferably AyV-dimethylformamide,
etc.), or aromatic solvents (preferably toluene or pyridine, etc.). Reaction temperature ranges from
about -20°C to 50°C, preferably about 0°C to 40°C.
The novel amide (T') of the present invention is reacted with a reducing agent in an inert

327
solvent to provide the novel amine (U') of the present invention. The reducing agent includes alkali
metal aluminum hydrides (preferably lithium aluminum hydride), alkati metal borohydrides
(preferably lithium borohydride), alkali metal trialkoxyaluminum hydrides (preferably lithium
tri-terf-butoxyaluminum hydride), dialkylaiuminum hydrides (preferably di-isobutylaluminum
hydride), borane, dialkylboranes (preferably di-isoamyl borane), alkali metal trialkylboron hydrides
(preferably lithium triethylboron hydride). The inert solvent includes ethereal solvents (preferably
tetrahydrofiiran or dioxane) or aromatic solvents (preferably toluene, etc.). Reaction temperature
ranges from about -78°C to 200°C, preferably about 50°C to 120°C.
Alternatively, the novel amine (U') of the present invention can be obtained by reductive
animation reaction using aldehyde (RiCHO) and a reducing agent in an inert solvent with or without
an acid. The reducing agent includes sodium triacetoxyborohydride., sodium cyanoborohydride,
sodium borohydride, or boran-pyridine complex, preferably sodium triacetoxyborohydride or sodium
cyanoborohydride. The inert solvent includes lower alkyl alcohol solvents (preferably methanol or
ethanol, etc.), lower halocarbon solvents (preferably dichloromethane, dichloroethane, or chloroform,
etc.), ethereal solvents (preferably tetrahydrofuran or dioxane), or aromatic solvents (preferably
toluene, etc.). The acid includes an inorganic acid (preferably hydrochloric acid or sulfuric acid) or
an organic acid (preferably acetic acid). Reaction temperature ranges from about -20°C to 120°C,
preferably about 0°C to 100°C. Also this reaction can be carried out under microwave conditions.
The novel urea (V) of the present invention can be obtained by urea reaction using an
isocyanate (R]NCO) in an inert solvent with or without a base. The base includes an alkali metal
carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogencarbonate (preferably sodium hydrogencarbonate or potassium hydrogencarbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably A^/Z-diisopropylethylamine, triethylamine, or JV-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine or imidazole, etc.). The inert solvent includes lower halocarbon solvents
(preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably
tetrahydrofuran or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or polar solvents
(preferably AyV-dimethylformamide or dimethyl sulfoxide, etc.). Reaction temperature ranges from

328
about -20°C to I20°C, preferably about 0°C to 100°C.
The amine (S') is reacted with a isothiocyanate (R]NCS) in an inert solvent with or without
a base to provide the novel thiourea (W) of the present invention. The base includes an alkali metal
carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogencarbonate (preferably sodium hydrogencarbonate or potassium hydrogen carbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably vVJV-diisopropylethylamine, triethylamine, or 7V-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine or imidazole, etc.). The inert solvent includes lower halocarbon solvents
(preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably
tetrahydrofuran or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or amide solvents
(preferably AyV-dimethylformamide, etc.). Reaction temperature ranges from about -20°C to 120°C,
preferably about 0°C to 100°C.
The novel urethane (X') of the present invention can be obtained by urethane reaction using
RiOCOCl, wherein X is halogen such as chloro, bromo, or iodo, in an inert solvent with or without a
base. The base includes an alkali metal carbonate (preferably sodium carbonate or potassium
carbonate, etc.), an alkali metal hydrogencarbonate (preferably sodium hydrogencarbonate or
potassium hydrogencarbonate, etc.), an alkali hydroxide (preferably sodium hydroxide or potassium
hydroxide, etc.), a tertiary amine (preferably AyV-diisopropylethylamine, triethylamine, or
TV-methylmorpholine, etc.), or an aromatic amine (preferably pyridine, imidazole, or
poly-(4-vinylpyridine), etc.). The inert solvent includes lower halocarbon solvents (preferably
dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably tetrahydrofuran
or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or polar solvents (preferably
A^^-dimethylformamide or dimethyl sulfoxide, etc.). Reaction temperature ranges from about -20°C
to 120°C, preferably about 0°C to I00°C.

329

Compounds of Formula (Y*) can be prepared as shown in Scheme 15. The coupling of the
amine (M), which is synthesized as scheme 3, with quinoline core (Q'), which is synthesized as
scheme 13, gives 2-substituted amino quinoline. The deprotection of Z-group is achieved by
hydrogen reduction to give compounds of Formula (Y')_

330

Compounds of Formula (Z') can be prepared as shown in Scheme 16. The coupling of the
amine (O), which is synthesized as scheme 4, with quinoline core (Q'), which is synthesized as
scheme 13, gives 2-substituted amino quinoline. The deprotection of Boc-group is achieved by an

acid to give the amine (Z').
The common intermediate (D") of the novel substituted pyrimidines can be prepared as
shown in Scheme 17. Commercially available substituted 2-hydroxy-pyrimidines (A"), wherein R2?
T, and p is as defined above, is converted to 2-halo-pyrimidines (B") by a halogenating agent with or

Til
without a base {wherein X is halogen such as chloro, bromo, or iodo). The halogenating agent
includes phosphorous oxychloride (POCI3), phosphorous oxybromide (POBr3), or phosphorus
pentachloride (PC15). The base includes a tertiary amine (preferably vV,iV-diisopropyIethylamine, etc.)
or an aromatic amine (preferably TVyV-dimethylaniline, etc.). Reaction temperature ranges from about
100°C to 200°C, preferably about 140°C to I80°C.
The halide (B") is substituted by the mono-protected diamine (D) , wherein R3, R4, A, and
B are as defined above and P is a protective group, with or without a base in an inert solvent to provide
2-substituted amino pyrimidine (C"). The base includes an alkali metal carbonate (preferably sodium
carbonate or potassium carbonate, etc.), an alkali metal hydroxide (preferably sodium hydroxide, etc.),
or a tertiary amine (preferably AyV-diisopropylethylamine, triethylamine, or jV-methylmorpholine,
etc.). The inert solvent includes lower alkyl alcohol solvents (preferably methanol, ethanol,
2-propanol, or butanol, etc.) or amide solvents (preferably A^-dimethylformamide or
l-methyl-pyrrolidin-2-one, etc.). Reaction temperature ranges from about 50°C to 200°C, preferably
about 80°C to 150°C. Also this reaction can be carried out under microwave conditions.
The deprotection of the protective group leads to the common intermediate (D") of the novel
substituted pyrimidines.


332
The conversion of the common intermediate (D") to the novel substituted pyrimidines
(E"-I") of the present invention is outlined in Scheme 18.
The amine (D") is reacted with a carboxylic acid (RiCO2H) and a dehydrating condensing
agent in an inert solvent with or without a base to provide the novel amide (E") of the present
invention. The dehydrating condensing agent includes dicyclohexylcarbodiimide (DCC),
l-ethyl-3-(3-dimethyIaminopropyI)carbodiimidehydrochloride (EDOHCI),
bromo-tris-pyrrolidino-phosnium hexafluorophosphate (PyBroP),
0-(7-azabenzotriazol-l-yl)-l,l,3,3-tetramethyluronium hexafluorophosphate (HATU), or
l-cyclohexyl-3-methylpoIystyrene-carbodiimide. The base includes a tertiary amine (preferably
./vyV-diisopropylethylarnine or triethylamine, etc.). The inert solvent includes lower halocarbon
solvents (preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents
(preferably tetrahydrofuran or dioxane), nitrile solvents (preferably acetonitrile, etc.), or amide
solvents (preferably AyV-dimethylformamide, etc.). In case of need, 1-hydroxybenzotriazole (HOBT),
HOBT-6-carboxaamidomethyl polystyrene, or l-hydroxy-7-azabenzotriazole (HOAT) can be used as
a reactant agent. Reaction temperature ranges from about -20°C to 50°C, preferably about 0°C to
40°C.
Alternatively, the novel amide (E") of the present invention can be obtained by amidation
reaction using an acid chloride (R[COC1) and a base in an inert solvent. The base includes an alkali
metal carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogencarbonate (preferably sodium hydrogencarbonate or potassium hydrogencarbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably JVyV-diisopropylethylamine, triethylamine, or JV-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine, imidazole, poly-(4-vinylpyridine), etc.). The inert solvent includes lower
halocarbon solvents (preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal
solvents (preferably tetrahydrofuran or dioxane), amide solvents (preferably ^TV-dimethylformamide,
etc.), or aromatic solvents (preferably toluene or pyridine, etc.). Reaction temperature ranges from
about -20°C to 50°C, preferably about 0°C to 40°C.
The novel amide (E") of the present invention is reacted with a reducing agent in an inert

333
solvent to provide the novel amine (F") of the present invention. The reducing agent includes alkali
metal aluminum hydrides (preferably lithium aluminum hydride), alkali metal borohydrides
(preferably lithium borohydride), alkali metal trialkoxyaluminum hydrides (preferably lithium
tri-tert-butoxyaluminum hydride), dialkylaluminum hydrides (preferably di-isobutylaluminum
hydride), borane, dialkylboranes (preferably di-isoarnyl borane), alkali metal trialkylboroa hydrides
(preferably lithium triethylboron hydride). The inert solvent includes ethereal solvents (preferably
tetrahydrofuran or dioxane) or aromatic solvents (preferably toluene, etc.). Reaction temperature
ranges from about -78°C to 200°C, preferably about 50°C to 120°C.
Alternatively, the novel amine (F") of the present invention can be obtained by reductive
amination reaction using aldehyde (RiCHO) and a reducing agent in an inert solvent with or without
an acid. The reducing agent includes sodium triacetoxyborohydride, sodium cyanoborohydride,
sodium borohydride, or boran-pyridine complex, preferably sodium triacetoxyborohydride or sodium
cyanoborohydride. The inert solvent includes lower alkyl alcohol solvents (preferably methanol or
ethanol, etc.), lower halocarbon solvents (preferably dichloromethane, dichloroethane, or chloroform,
etc.), ethereal solvents (preferably tetrahydrofuran or dioxane), or aromatic solvents (preferably
toluene, etc.). The acid includes an inorganic acid (preferably hydrochloric acid or sulfuric acid) or
an organic acid (preferably acetic acid). Reaction temperature ranges from about -20°C to 120°C,
preferably about 0°C to 100°C. Also this reaction can be carried out under microwave conditions.
The novel urea (G") of the present invention can be obtained by urea reaction using an
isocyanate (R]NCO) in an inert solvent with or without a base. The base includes an alkali metal
carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogencarbonate (preferably sodium hydrogencarbonate or potassium hydrogen carbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably AyV-diisopropylethylamine, triethylamine, or iV-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine or imidazole, etc.). The inert solvent includes lower halocarbon solvents
(preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably
tetrahydrofuran or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or polar solvents
(preferably AyV-dimethylformamide or dimethyl sulfoxide, etc.). Reaction temperature ranges from

334
about -20°C to 120°C, preferably about 0°C to I00°C.
The amine (D") is reacted with a isothiocyanate (RiNCS) in an inert solvent with or without
a base to provide the novel thiourea (H") of the present invention. The base includes an alkali metal
carbonate (preferably sodium carbonate or potassium carbonate, etc.), an alkali metal
hydrogen carbon ate (preferably sodium hydrogencarbonate or potassium hydrogen carbonate, etc.), an
alkali hydroxide (preferably sodium hydroxide or potassium hydroxide, etc.), a tertiary amine
(preferably A^^-diisopropylethylamine, triethylamine, or N-methylmorpholine, etc.), or an aromatic
amine (preferably pyridine or imidazole, etc.). The inert solvent includes lower halocarbon solvents
(preferably dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably
tetrahydrofuran or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or amide solvents
(preferably AyV-dimethylformamide, etc.). Reaction temperature ranges from about -20°C to 120°C,
preferably about 0°C to 100°C.
The novel urethane (I") of the present invention can be obtained by urethane reaction using
RiOCOCl, wherein X is halogen such as chloro, bromo, or iodo, in an inert solvent with or without a
base. The base includes an alkali metal carbonate (preferably sodium carbonate or potassium
carbonate, etc.), an alkali metal hydrogencarbonate (preferably sodium hydrogencarbonate or
potassium hydrogencarbonate, etc.), an alkali hydroxide (preferably sodium hydroxide or potassium
hydroxide, etc.), a tertiary amine (preferably T^V-dnsopropylethylamine, triethylamine, or
jV-methylmorpholine, etc.), or an aromatic amine (preferably pyridine, imidazole, or
poly-(4-vinylpyridine), etc.). The inert solvent includes lower halocarbon solvents (preferably
dichloromethane, dichloroethane, or chloroform, etc.), ethereal solvents (preferably tetrahydrofuran
or dioxane), aromatic solvents (preferably benzene or toluene, etc.), or polar solvents (preferably
A^JV-dimethylformamide or dimethyl suifoxide, etc.). Reaction temperature ranges from about -20°C
to 120°C, preferably about 0°C to 100°C.

335

Compounds of Formula (J") can be prepared as shown in Scheme 19. The coupling of the
amine (M), which is synthesized as scheme 3, with pyrimidine core (B"), which is synthesized as
scheme 17, gives 2-substituted amino pyrimidine. The deprotection of Z-group is achieved by
hydrogen reduction to give compounds of Formula (J").

336

Compounds of Formula (K") can be prepared as shown in Scheme 20. The coupling of the
amine (O), which is synthesized as scheme 4, with pyrimidine core (B"), which is synthesized as
scheme 17, gives 2-substituted amino pyrimidine. The deprotection of Boc-group is achieved by an
acid to give the amine (K").

Alternatively, the novel quinoline (M"), the novel tetrahydroquinazoline (N"), the novel
pyrimidine (O"), the novel quinoline (P"), and the novel pyrimidine (Q') of the present invention are

337
directly synthesized from the quinoline core (C), which is synthesized in Scheme 1, the
tetrahydroquinazoline core (T), which is synthesized in Scheme 5, the pyrimidine core (F'), which is
synthesized in Scheme 9, the quinoline core (Q'), which is synthesized in Scheme 13, and the
pyrimidine core (B"), which is synthesized in Scheme 17, as shown in Scheme 21. This coupling is
performed with or without a base in an inert solvent. The base includes an alkali metal carbonate
(preferably sodium carbonate or potassium carbonate, etc.), an alkali metal hydroxide (preferably
sodium hydroxide, etc.), or a tertiary amine (preferably TV^jV-diisopropylethylamine, triethylamine, or
/V-methylmorpholine, etc.). The inert solvent includes lower alkyl alcohol solvents (preferably
methanol, ethanol, 2-propanol, or butanol, etc.) or amide solvents (preferably
A^-dimethylformamide or l-methyl-pyrrolidin-2-one, etc.). Reaction temperature ranges from about
50°C to 200°C, preferably about 80°C to 180°C. Also this reaction can be carried out under microwave
conditions.

338

For example, compounds of Formula (T") can be prepared as shown in Scheme 22. The
amine (O), which is synthesized in Scheme 4, is subjected to reductive amination by aldehyde
(RiCHO). The deprotection of Boc-group is achieved by an acid to give the amine. The coupling of

339
the amine with pyrimidine core (F'), which is synthesized as scheme 9, gives the novel pyrimidine
(T") of the present invention.

quinoline (W") of the present invention.
Compounds of Formula (W") can be prepared as shown in Scheme 23. The amine (O),
which is synthesized in Scheme 4, is subjected to amidation by carboxylic acid (RiCC^H) or acid
chloride (RjCOCI). The deprotection of Boc-group is achieved by an acid to give the amine. The
coupling of the amine with quinoline core (Q'), which is synthesized as scheme 13, gives the novel


340
Compounds of Formula (Z") can be prepared as shown in Scheme 24. The amine (O), which
is synthesized in Scheme 4, is subjected to amidation by carboxylic acid (R1CO7H) or acid chloride
(RiCOCl). The deprotection of Boc-group is achieved by an acid to give the amine. The coupling of
the amine with pyrimidine core (B"), which is synthesized as scheme 17, gives the novel pyrimidine
(Z") of the present invention.

When a compound of the invention contains optical isomers, stereoisomers, regio isomers,
rotational isomers, a single substance and a mixture of them are included as a compound of the
invention. For example, when a chemical formula is represented as showing no stereochemical
designation(s), such as Formula VI, then all possible stereoisomer, optical isomers and mixtures
thereof are considered within the scope of that formula. Accordingly, Formula VII, specifically
designates the cis relationship between the two amino groups on the cyclohexyl ring and therefore this
formula is also fully embraced by Formula VI.
Other uses of the disclosed invention will become apparent to those in the art based upon,
inter alia, a review of this patent document.
The following examples are given to illustrate the invention and are not intended to be
inclusive in any manner:

341
Examples
The compounds of the invention and their synthesis are further illustrated by the following
examples. The following examples are provided to further define the invention without, however,
limiting the invention to the particulas of these examples. "Ambient temperature" as referred to in the
following example is meant to indicate a temperature falling between 0 °C and 40 °C. The following
compounds are named by Beilstein Auto Nom Version 4.0, CS Chem Draw Ultra Version 6.0, CS
Chem Draw Ultra Version 6.0.2, CS Chem Draw Ultra Version 7.0.1, or ACD Name Version 7.0.
Abbreviations used in the instant specification, particularly the Schemes and Examples, are
as follows:
*H NMR : proton nuclear magnetic resonance spectrum
AcOH : acetic acid
APCI: atmospheric pressure chemical ionization
(Boc)2O : di-tertiary-butyl dicarbonate
BuLi: butyl lithium
BuOH : butanol
Cbz : carbobenzoxy
CDCI3 : deuterated chloroform
CH2CI2 : dichloromethane
CHCI3 : chloroform
CI: chemical ionization
mCPBA: meta chloroperbenzoic acid
DMA: N,N-dimethyl acetamide
DC1-5 : dichloromethane
DIEA : diisopropylethylamine
DMSO : dimethyl sulfoxide
Dppf: bis-(diphenylphosphino)ferrocene

342
El: electron ionization
ESI: electrospray ionization
Et2O : diethyi ether
EtOAc : acetic acid ethyl ester
EtOH : ethanol
FAB : fast atom bombardment
HATU : 0-(7-azabenzotriazoI-I-yl)-iV^^yV'-tetramethyluronium-
Hexafluoro phosphate
H?SO4: sulfuric acid
HC1: hydrogen chloride
IPA: isopropanol
K2CO3 : potassium carbonate
Me2NH : dimethylamine
MeNH2 : methylamine
MeOH : methanol
MgSO4 : magnesium sulfate
MsOH : methanesulfonic acid
NaBH(OAc)3 : sodium triacetoxyborohydride
NaBH3CN : sodium cyanoborohydride
NaBH4 : sodium borohydride
NaHCO3 : sodium hydrogencarbonate
Pd/C : palladium carbon
POCI3 : phosphoryl chloride
PVP : poly(4-viny!pyridine)
SOC12: thionyl chloride
TBME: tert-butyl methyl ether
TFA : trifluoroacetic acid
THF : tetrahydrofuran

343
ZC1: benzyloxycarbonyl chloride
s : singlet
d : doublet
t : triplet
q : qualtet
dd : doublet doublet
dt: doublet triplet
ddd : doublet doublet doublet
brs : broad singlet
m : multiplet
J: coupling constant
Hz : Hertz
Example 1
Ar2-[cw-4-(4-Bromo-2-trifluoromethoxy-benzy])-amino-cyclohexyI]-A^-methyl-quinoline-2,4-
din mine dihydrochloride
Step A: Synthesis of 2,4-dichIoro-quinoline.
A suspension of quinoline-2,4-diol (150 g, 931 mmol) in POC13 (975 mL, 10.4 mol) was
stirred at reflux for 6 hr and the reaction mixture was concentrated. The residue was diluted with
CHCI3 (500 mL) and the solution was poured into ice water. The aqueous layer was extracted with
CHCI3 (three times). The combined organic layer was dried over MgSO4, filtrated, concentrated, and
purified by flash chromatography (silica gel, 20% EtOAc in hexane) to give 2,4-dichloro-quinoline
(177 g, 96%) as a pale brown solid.
EIMSm/el97, M+;'HNMR (300 MHz, CDCI3) 8 7.50 (s, 1 H), 7.65 (ddd, J= 8.3, 7.0, 1.3 Hz, 1
H), 7.79 (ddd, J= 8.5, 7.0, 1.3 Hz, t H), 8.00-8.06 (m, 1 H), 8.16-8.21 (m, 1 H).

344
Step B: Synthesis of (2-c hloro-qui noli n-4-yl)-m ethyl-am in e.
To a solution of 2,4-dichloro-quinoline (29.8 g, 150 mmol) in THF (300 mL) was added 40%
MeNH? in water (58.4 g, 752 mmoi). The mixture was stirred at ambient temperature for 12 days and
concentrated. The residue was suspended in CHCI3 and H2O. The precipitate was collected by
filtration, washed with acetone, and dried at 50 °C under reduced pressure to give (2-chIoro-quinoIin-
4-yl)-methyl-amine (13.2 g, 45%) as a colorless solid.
ESI MS m/e 215, M + Na+ ; lH NMR (300 MHz, DMSO-d6) 5 2.91 (d, J= 4.7 Hz, 3 H), 6.35 (s, 1
H), 7.47 (ddd,J- 8.3, 6.6, 1.7 Hz, 1 H), 7.62-7.75 (m, 3 H), 8.16 (d,J = 8.6 Hz, 1 H).
Step C: Synthesis of (c&-4-benzyloxycarbonylamino-eyclohexyl)-carbaniic acid- benzyl ester.
To a suspension of cis-cyclohexane-l,4-dicarboxylic acid (25.0 g, 145 mmol) in benzene (125
mL) were added phosphorazidic acid dipbenyl ester (81.9 g, 298 mmol) and triethylamine (30.1 g, 297
mmol). The reaction mixture was stirred at reflux for 2.5 hr. Benzyl alcohol (32.2 g, 298 mmol) was
added and the mixture was stirred at reflux for 24 hr. The reaction mixture was concentrated and the
residue was dissolved in EtOAc and H2O. The organic layer was separated and the aqueous layer was
extracted with EtOAc (twice). The combined organic layer was washed with 1 M aqueous KHSO4,
saturated aqueous NaHCOs, and brine, dried over MgSO4, filtrated, concentrated, and purified by
flash chromatography (silica gel, 33% EtOAc in hexane) to give (cis-4-benzyloxycarbonylamino-
cyclohexyl)-carbamic acid benzyl ester (52.0 g, 94%) as a colorless oil.
ESI MS m/e 405, M + Na+; *H NMR (300 MHz, CDCI3) 5 1.45-1.60 (m, 4 H), 1.60-1.80 (m, 4 H),
3.52-3.80 (m, 2 H), 4.70-5.00 (m, 2 H), 5.07 (s, 4 H), 7.15-7.40 (m, 10 H).
Step D: Synthesis of (c/y-4-amino-cyclohexyl)-carbamic acid tert-buty} ester.
To a solution of (ds-4-benzyloxycarbonylamino-cyclohexyl)-carbamic acid benzyl ester
(91.7 g, 240 mmol) in MeOH (460 mL) was added 5% Pd/C (9.17 g). The reaction mixture was
stirred at ambient temperature under hydrogen atmosphere for 2.5 days, filtrated through a pad of
celite, and concentrated to give a diamine as a colorless oil. To a solution of the diamine in MeOH
(550 mL) was added a solution of (Boc^O (6.59 g, 30.2 mmol) in MeOH (80 mL) dropwise over 4 hr.

345
The reaction mixture was stirred at ambient temperature for 1.5 days and concentrated. After
dissolution with H2O, the aqueous layer was extracted with CHC13 (three times). The combined
organic layer was dried over MgSO4, filtrated, and concentrated to give (cw-4-amino-cyck>hexyl)-
carbamic acid rer/-butyl ester (7.78 g, 15%, crude) as a colorless oil. The aqueous layer was
concentrated and the residue was dissolved in MeOH, dried over MgSO4, filtrated, and concentrated
to give a recovered diamine (32.9 g) as a colorless oil. To a solution of the recovered diamine (32.9
g, 288 mmol) in MeOH (660 mL) was added a solution of (Boc)20 (6.29 g, 28.8 mmol) in MeOH (80
mL) dropwise over 5 hr. The reaction mixture was stirred at ambient temperature for 10 hr and
concentrated. After dissolution with H2O, the aqueous layer was extracted with CHC13 (three times).
The combined organic layer was dried over MgSO4, filtrated, and concentrated to give (cw-4-amino-
cyclohexyl)-carbamic acid tert-buty\ ester (8.16 g, 16%, crude) as a colorless oil. The aqueous layer
was concentrated and the residue was dissolved in MeOH, dried over MgSO4, filtrated, and
concentrated to give a recovered diamine (23.1 g) as a colorless oil. To a solution of the recovered
diamine (23.1 g, 202 mmol) in MeOH (462 mL) was added a solution of (Boc)2O (4.42 g, 20.3 mmol)
in MeOH (56 mL) dropwise over 4 hr. The reaction mixture was stirred at ambient temperature for
3.5 days and concentrated. After dissolution with H2O, the aqueous layer was extracted with CHC13
(three times). The combined organic layer was dried over MgSO4, filtrated, and concentrated to give
(c/s-4-amino-cyC1-5hexyl)-carbamic acid tert-butyl ester (5.01 g, 10% based on starting material) as a
colorless oil. The aqueous layer was concentrated and the residue was dissolved in MeOH, dried over
MgSO4, filtrated, and concentrated to give a recovered diamine (16.0 g) as a colorless oil. To a
solution of the recovered diamine (16.0 g, 140 mmol) in MeOH (320 mL) was added a solution of
(Boc)2O (3.06 g, 14.0 mmol) in MeOH (40 mL) dropwise over 4 hr. The reaction mixture was stirred
at ambient temperature for 13 hr and concentrated. After dissolution with H2O, the aqueous layer was
extracted with CHC13 (three times). The combined organic layer was dried over MgSO4, filtrated, and
concentrated to give (c«-4-amino-cyclohexyl)-carbamic acid tert-butyl ester (3.53 g, 7% based on the
starting material) as a colorless oil. The aqueous layer was concentrated and the residue was dissolved
in MeOH, dried over MgSO4, filtrated, and concentrated to give a recovered diamine (11.1 g) as a
colorless oil.

346
ESI MS m/e 215, M + H+; *H NMR (300 MHz, CDC13) 5 1.20-1.80 (m, 8 H), 1.44 (s, 9 H), 2.78-2.95
(m, 1 H), 3.50-3.80 (m, 1 H), 4.30-4.82 (m, 1 H).
Step E: Synthesis of Af2-(cw-4-amino-cyclohexyl)-Ar*-methyl-quinoIine-2,4-diamine.
A mixture of (2-chloro-quinolin-4-yl)-methyI-amine (2.00 g, 10.4 mmol) and (cis-4-sim'mo-
cyclohexyl)-carbamic acid ter(-buty\ ester (2.45 g, 11.4 mmol) in butanol (3 mL) was stirred at 130 °C
for 2 days in a sealed tube. The reaction mixture was poured into saturated aqueous NaHCO3 and the
aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over
MgSO4, filtrated, concentrated, and purified by medium-pressure liquid chromatography (NH-silica
gel, 20% EtOAc in hexane) to give [cw-4-(4-methylamino-quinolin-2-ylamino)-cyclohexyI]-carbamic
acid tert-butyl ester (1.45 g) as a pale yellow oil. To a solution of the above material (1.31 g)in£tOAc
(15 mL) was added 4 M hydrogen chloride in EtOAc (30 mL). The reaction mixture was stirred at
ambient temperature for 5 hr. The precipitate was collected by filtration and dissolved in saturated
aqueous NaHCO3. The aqueous layer was extracted with CHCI3 (three times). The combined organic
layer was dried over MgSO4, filtrated, and concentrated to give TV -(cw-4-amino-cyclohexyl)-A'4-
methyl-quinoline-2,4-diamine (999 mg, 40%) as a pale yellow solid.
El MS m/e 271 M + H+; 'H NMR (300 MHz, DMSO-d6) 5 1.42-1.92 (m5 8 H), 2.81 (d,J=4.7Hz,
3 H), 2.89-3.01 (m, 1 H), 3.17 (s, 2 H), 4.07 (brs, 1 H), 5.77 (s, 1 H), 6.32 (d, 7= 6.5 Hz, 1 H),
6.69-6.80 (m, 1 H), 6.94-7.06 (m, 1 H), 7.34 (d, J= 3.7 Hz, 2 H), 7.85 (d, J = 8.2 Hz, 1 H).
Step F: Synthesis of 4-bromo-2-trif1uoromethoxy-benzaIdehyde.
A solution of 4-bromo-l-iodo-2-trifiuoromethoxy-benzene (1.00 g, 2.72 mmol) in THF (15
mL) was cooled to -78 °C and 2.66 M BuLi in hexane (2.05 mL, 5.44 mmol) was added dropwise.
The reaction mixture was stirred at -78 °C for 1.5 h and jV-formylmorpholine (0.57 mL, 5.63 mmol)
was added. The reaction mixture was stirred at -78 °C for 15 min and at ambient temperature for 80
min. The reaction was quenched with 0.25 M aqueous citric acid (10 mL) and the resulting mixture
was extracted with EtOAc (three times). The combined organic layer was dried over MgSOj, filtrated,
concentrated, and purified by flash chromatography (silica gel, 2% to 5% EtOAc in hexane) to give

347
4-bromo-2-trifluoromethoxy-benzaldehyde (560 mg, 77%) as a pale brown solid.
CI MS m/e 269, M + H~; !H NMR (300 MHz, CDCI3) 5 7.50-7.67 (m, 2 H), 7.85 (d, J= 8.1 Hz, 1
H), 10.33 (s, 1 H).
Step G: Synthesis of Ar2-[c/5-4-(4-bromo-2-trifluoromethoxy-benzyI)-amino-cyclohexyI]-A'4-
methyl-quinoline~2,4-diamine dihydrochloride.
To a solution of ^-(c/s^-ammo-cyC1-5hexy^-A^-methyl-quinoline^^-diamine (370 mg, 1.37
mmol) in methanol (4 mL) were added 4-bromo-2-trifluoromethoxy-benzaldehyde (368 mg, 1.37
mmol), acetic acid (82 mg, 1.37 mmol), and NaBHsCN (129 mg, 2.05 mmol). The reaction mixture
was stirred at ambient temperature for 20 hr. The reaction was quenched with saturated aqueous
NaHCO3 and the aqueous layer was extracted with CHCI3 (three times). The combined organic layer
was dried over MgSO4, filtrated, concentrated, and purified by medium-pressure liquid
chromatography (NH-silica gel, 20% EtOAc in hexane) and flash chromatography (silica gel, 5%
MeOH in CHCI3) to give a colorless oil. To a solution of the above oil in EtOAc (2 mL) was added
4 M hydrogen chloride in EtOAc (5 mL). The mixture was stirred at ambient temperature for 1 hr and
concentrated. A suspension of the residue in Et2O (12 mL) was stirred at ambient tempareture for 1
hr. The precipitate was collected by filtration, washed with Et2O, and dried under reduced pressure to
give A'2-[c/5-4-(4-bromo-2-trifluoromethoxy-ben2yl)-amino-cyclohexyl]-jV4-methyl-
quinoline-2,4-diamine dihydrochloride (365 mg, 45%) as a white solid.
ESI MS m/e 523, M (free) + H+ ; !H NMR (300 MHz, DMSO-d5) 5 1.61-2.11 (m, 8 H), 2.96 (d, J =
4.4 Hz, 3 H), 3.19-3.41 (m, 2 H), 4.11-4.34 (m, 2 H), 5.92 (brs, 1 H), 7.40 (t, J= 8.2 Hz, 1 H),
7.63-7.79 (m, 3 H), 7.93 (d, J= 8.4 Hz, 1 H), 8.22 (d, J= 8.2 Hz, 1 H), 8.30-8.48 (m, 2 H), 9.59 (brs,
2H).
Example 2
7V2-{c/y-4-[2-(4-Bromo-2-trifluoromethoxy-phenyI)-ethy1amino]-cyclohexyl}-Ar4-methyl-
quinoline2,4-diamine dihydrochloride

348
Step A: Synthesis of (4-bromo-2-trifluoromethoxy-phenyl)-acetaldehyde.
To a suspension of (methoxymethyl)-triphenylphosphonium chloride (5.29 g, 14.9 mol) in
Et2O (50 mL) was added 1.8 M phenyl lithium in 30% Et2O in cyclohexane (8.58 mL, 15.5 mmol).
The mixture was stirred at ambient temperature for 10 min. To the reaction mixture was added
4-bromo-2-trifluoromethoxy-benzaldehyde obtained in step F of example 1 (4.00 g, 14.9 mmol) in
Et2O (18 mL). The mixture was stirred at ambient temperature for 4 hr, filtrated and concentrated.
To the above residue was added 10% H2SO4 in AcOH (40 mL). The mixture was stirred at ambient
temperature for 90 min. The solution was poured into H2O and the aqueous layer was extracted with
CHCI3 (three times). The combined organic layer was washed with saturated aqueous NaHCO3 and
brine, dried over MgSO4, filtrated, concentrated, and purified by flash chromatography (silica gel, 9%
EtOAc in hexane) to give (4-bromo-2-trifluoromethoxy-phenyl)-acetaldehyde (1.25 g, 30 %) as a pale
brown oil.
ESI MS m/e 284, M + H+; 'H NMR (200 MHz, CDC13) 3 3.75 (d, J = 1.5 Hz, 2 H), 7.16 (d, J= 8.4
Hz, 1 H), 7.41-7.51 (m, 2 H), 9.74 (t, J= 1.5 Hz, 1 H).
Step B: Synthesis of A^-Jcj-s^-IZ-^-bromo^-trifluoromethoxy-phenyO-ethylamino]-
cyclohexyl}-A^-methyl-quino!ine-2,4-diamine dihydrochloride.
Using the procedure for the step G of example 1, the title compound was obtained.
ESI MS m/e 537, M (free) + H+ ; 'H NMR (300 MHz, DMSO-d6) 8 1.62-2.06 (m, 8 H), 2.96 (d, J =
4.4 Hz, 3 H), 3.04-3.39 (m, 5 H), 4.17 (brs, 1 H), 5.90 (brs, 1 H), 7.40 (t,J= 8.2 Hz, 1 H), 7.52 (d, J
= 8.7 Hz, 1 H), 7.57-7.85 (m, 3 H), 8.20 (d,J= 8.2 Hz, 1 H), 8.26-8.47 (m, 2 H), 9.23 (brs, 2 H).
Example 3
^-{^-^[(^Bromo-l-trifluoromethoxy-benzy^-amino-niethylj-cyclohexylJ-A^-methyl-
quinoline-2,4-diamine dihydrochloride

349
Step A: Synthesis of (c«-4-hydroxymethyl-cyclohexyl)-carbamic acid /erf-butyl ester.
A suspension of c/s-4-amino-cyclohexanecarboxylic acid (244 g, 1.70 mol) in MeOH (2.45
L) was cooled to -8 °C . Thionyl chloride (45.0 mL, 617 mmol) was added dropwise. The resulting
solution was stirred at ambient temperature for 4.5 hr and concentrated to give a white solid. To a
suspension of the above solid in CHC13 (3.00 L) were added triethylamine (261 mL, 1.87 mol) and
(Boc)2O (409 g, 1.87 mol) successively. The reaction mixture was stirred at ambient temperature for
5 hr and poured into water. The aqueous layer was extracted with CHCI3 (three times). The combined
organic layer was dried over MgSO4, filtrated, concentrated, and purified by flash chromatography
(silica gel, CHC13 only to 10% MeOH in CHCI3) to give a colorless oil (531 g). To a suspension
cooled at -4 °C of lithium aluminum hydride (78.3 g, 2.06 mol) in Et2O (7.9 L) was added a solution
of the above oil (530.9 g) in Et2O (5.3 L) below 0 °C. The resulting suspension was stirred at ambient
temperature for 2 hr. The reaction mixture was cooled on an ice-bath, quenched with cold water, and
filtrated through a pad of celite. The filtrate was dried over MgSO4, filtrated, and concentrated. The
precipitate was suspended in hexane (300 mL), filtrated, washed with hexane, and dried under
reduced pressure to give (cz>4-hydroxymethyl-cyclohexyl)-carbamic acid /erf-butyl ester (301 g,
77%) as a white solid.
ESIMSm/e252,M + Na+;'HNMR(300MHz,CDCl3)51.16-1.36(m;2H), 1.45 (s, 9 H), 1.52-1.77
(m, 7 H), 3.51 (d, J = 6.2 Hz, 2 H), 3.75 (brs, 1 H), 4.30-4.82 (m, 1 H).
Step B: Synthesis of [c&-4-(benzyIoxycarbonylamino-methyl)-cyclohexyI]-carbamic acid
terf-butyl ester.
To a solution of (c/5-4-hydroxymethyl-cyclohexyl)-carbamic acid fer/-butyl ester (17.7 g,
77.2 mmol) in THF (245 mL) were added triphenylphosphine (20.2 g, 77.0 mmol) and phthalimide
(11.4 g, 77.5 mmol) successively. The resulting suspension was cooled on an ice-bath and 40%
diethyl azodicarboxylate in toluene (33.6 mL, 74.1 mmol) was added over 1 hr. The reaction mixture
was stirred at ambient temperature for 2.5 days, concentrated, and purified by flash chromatography
(silica gel, 33% EtOAc in hexane) to give a white solid. To a suspension of the above solid (27.5 g)
in EtOH (275 mL) was added hydrazine hydrate (5,76 g, 115 mmol). The mixture was stirred at reflux

350
for 2.25 hr, cooled, and concentrated. The precipitate was dissolved in 10% aqueous sodium
hydroxide (350 mL). The aqueous layer was extracted with CHC13 (three times). The combined
organic layer was dried over MgSO4, filtrated, and concentrated. To a solution of the above residue in
CHCI3 (275 mL) was added triethylamine (8.54 g, 84.4 mmol). The resulting solution was cooled to
0 °C and ZC1 (14.4 g, 84.4 mmol) was added below 5 °C. The reaction mixture was stirred at ambient
temperature for 16 hr and poured into saturated aqueous NaHCO3. The aqueous layer was extracted
with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtrated, concentrated,
and purified by flash chromatography (silica gel, 2% MeOH in CHC13) to give
[c/5-4-(benzyIoxycarbonylamino-methyl)-cyclohexyl]-carbamic acid tert-buty\ ester (25.3 g, 91%) as
a colorless oil.
ESIMSm/e385,M + Na+;lHNMR(300MHz,CDCl3)8 1.13-1.31 (m, 2 H), 1.44 (s, 9 H), 1.48-1.75
(m, 7 H), 3.10 (t, J- 6.4 Hz, 2 H), 3.72 (brs, 1 H), 4.42-4.76 (m, 1 H), 4.76-4.92 (m, 1 H), 5.09 (s, 2
H), 7.27-7.38 (m, 5 H).
Step C: Synthesis of (m-4-amino-cyclohexylmethyl)-carbamic acid benzyl ester.
To a solution of [c/s-4-(benzyIoxycarbonyIamino-methyl)-cyC1-5hexyI]-carbamic acid
tert-butyl ester (12.9 g, 35.6 mmol) in EtOAc (129 mL) was added 4 M hydrogen chloride in EtOAc
(129 mL). The reaction mixture was stirred at ambient temperature for 3 hr, filtrated, washed with
EtOAc, and dried under reduced pressure. The solid was dissolved in saturated aqueous NaHCO3.
The aqueous layer was extracted with CHCI3 (five times). The combined organic layer was dried over
MgSO4, filtrated, concentrated, and dried under reduced pressure to give (cw-4-amino-
cyclohexylmethyl)-carbamic acid benzyl ester (8.88 g, 95%) as a colorless oil.
ESI MS m/e 263, M + H+;'HNMR (300 MHz, CDC13) 5 1.36-1.98 (m, 9 H), 2.96-3.32 (m, 3 H), 5.12
(brs, 3 H), 7.36 (s, 5 H).
Step D: Synthesis of [c/s-4-(4-methylamino-quinolin-2-ylamino)-cyclohexylmethyl]-carbamic
acid benzyl ester.
A mixture of (2-chloro-quinolin-4--yl)-rnethyl-amine obtained in step B of example 1 (2.00 g,

351
10.4 mmol) and (c/s-4-amino-cyclohexylmethyl)-carbamic acid benzyl ester (3.27 g, 12.5 mtnol) in
butanol (3 mL) was stirred at 130 °C for 16 hr in a sealed tube. The reaction mixture was poured into
saturated aqueous NaHCO3, and the aqueous layer was extracted with CHC13 (three times). The
combined organic layer was dried over MgSO4, filtrated, concentrated, and purified by flash
chromatography (silica, 10% MeOH in CHC13) to give [c/s-4-(4-methylamino-quinolin-2-
ylamino)-cyclohexylmethyi]-carbamic acid-benzyl ester (2.16 g, 49%) as a white solid.
ESI MS m/e 419, M + H+ ; *H NMR (300 MHz, CDC13) 5 1.42-1.99 (m, 9 H), 3.05 (d, J= 4.7 Hz, 3
H), 3.08-3.16 (m, 2 H), 3.81 (brs, 1 H), 5.07 (s, 2 H), 5.18-5.28 (m, 1 H), 5.34 (s, 1 H), 7.07-7.18 (m,
1 H), 7.22-7.45 (m, 6 H), 7.56-7.70 (m, 1 H), 8.16 (d,J= 8.4 Hz, 1 H), 8.23 (d, J= 7.6 Hz, 1 H), 12.76
(brs, 1 H).
Step E: Synthesis of iV2-{c/s-4-[(4-bromo-2-trifiuoromethoxy-benzyl)-amino-methyl]-
cyclohexyl}-A^-methyl-quinoline-2,4-diamine dihydrochloride.
To a solution of [c/j-4-(4-methylamino-quinolm-2-ylamino)-cyclohexylmethyI]-
carbamic acid-benzyl ester (2.02 g, 4.83 mmol) in MeOH (20 mL) was added 10% Pd/C (202 mg).
The mixture was stirred at 50 °C under hydrogen atmosphere for 23.5 hr. The reaction mixture was
filtrated through a pad of celite and concentrated. To a solution of the residue (500 mg) in methanol
(5 mL) were added 4-bromo-2-trifluoromethoxy-benzaldehyde obtained in step F of example 1 (497
mg, 1.85 mmol), acetic acid (111 mg, 1.85 mmol), and NaBH3CN (166 mg, 2.64 mmol). The reaction
mixture was stirred at ambient temperature for 23 hr. The reaction was quenched with saturated
aqueous NaHCOs and the aqueous layer was extracted with CHC13 (three times). The combined
organic layer was dried over MgSO4, filtrated, concentrated, and purified by medium-pressure liquid
chromatography (NH-silica gel, 50% EtOAc in hexane) and flash chromatography (silica gel, 2% to
50% MeOH in CHC13) to give a colorless oil. To a solution of the above oil in EtOAc (2 mL) was
added 4 M hydrogen chloride in EtOAc (5 mL). The mixture was stirred at ambient temperature for
1 hr and concentrated. A suspension of the residue in Et2O (12 mL) was stirred at ambient tempareture
for 1 hr. The precipitate was collected by filtration, washed with Et2O, and dried under reduced
pressure to give N -{c/s-4-[(4-bromo-2-trifluoromethoxy-benzyI)amino-

352
methyl]-cyC1-5hexyl}-V-methyl-quinoline-2,4-diamine dihydrochloride (147 mg, 14%) as a white
solid.
ESI MS m/e 537, M (free) + H+ ; 'H NMR (300 MHz, CDCI3) 5 1.34-2.15 (m, 9 H), 2.63-3.08 (m, 5
H), 3.41-3.88 (m, 1 H), 4.28 (s, 2 H), 7.00-7.62 (m, 6 H), 7.65-8.38 (m, 3 H), 10.01 (brs, 2 H), 11.76
(brs, 1 H).
Example 4
A^-Methy1-Ar2-{c/s-4-[(2-trifluoromethoxy-benzyl)-ainino-methyl]-cyclohexyl}-quinoline-2,4-
diamine dihydrochloride
Step A: Synthesis of A^-methyl-A^-{ciy-4-[(2-trifluoromethoxy-benzyl)-amino-methyl]-
cyclohexyl}-quinoline-2,4-diamine dihydrochloride.
To a solution of A'2-{c/5-4-[(4-bromo-2-trifluoromethoxy-benzyl)amino-methyl]-
cyclohexylJ-A^-methyl-quinoIine^^-diamine obtained in step E of example 3 (250 mg, 0.465 mmol)
in EtOH (2.5 mL) was added 10% Pd/C (75 mg). The mixture was stirred at ambient temperature
under hydrogen atmosphere for 15 hr. The reaction mixture was filtrated through a pad of celite and
purified by flash chromatography (NH-silica gel, 50% EtOAc in hexane) to give a colorless oil. To
a solution of the above oil in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (5 mL). The
mixture was stirred at ambient temperature for 1 hr and concentrated. The residue was suspended with
Et2O (10 mL) and stirred at ambient tempareture for 1 hr. The precipitate was collected by filtration,
washed with Et?O and dried under reduced pressure to give 7V4-methyl-Ar2-{ci5-4-[(2-
trifluoromethoxy-benzyl)amino-methyl]-cyC1-5hexyl}-quinoIine-2,4-diamine dihydrochloride (114
mg, 46% ) as a white solid.
ESI MS m/e 459, M (free) + H+ ; lH NMR (300 MHz, CDC13) 5 1.46-2.09 (m, 9 H), 2.84 (brs, 3 H),
2.92 (brs, 2 H), 3.60-3.82 (m, 1 H), 4.32 (s, 2 H), 7.05-7.49 (m, 6 H), 7.88 (d, J= 7.8 Hz, 1 H),
8.11-8.35 (m, 2 H), 9.91 (brs, 2 H), 11.83 (s, t H).

353
Example 5
Ar2-[cw-4-(4-Bromo-2-trifluoromethoxy-benzyl)-amino-cyclohexyl]-Arl^V4-dimethyl-quinoline-
2,4-diamine dihydrochloride
Step A: Synthesis of (2-chloro-quinolin-4-yl)-dimethyI-amine.
To a solution of 2,4-dichloro-quinoline (177 g, 894 mmol) in THF (2.1 L) was added 50%
aqueous Me2NH (234 mL, 2.23 mol). The mixture was stirred at ambient temperature for 68 hr. To
the mixture was added 50% aqueous Me2NH (47 mL, 448 mmol) and stirred at ambient temperature
for 3 hr. The solution was poured into saturated aqueous NaHCO3 and the aqueous layer was
extracted with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtrated,
concentrated, and purified by flash chromatography (NH-silica, 1% to 3% EtOAc in hexane) to give
(2-chloro-quinolin-4-yl)-dimethyl-amine (75.9 g, 41%) as a pale yellow oil and (4-chloro-
quinolin-2-yl)-dimethyI-amine (28.0 g, 15%) as a pale yellow oil.
(2-chloro-quinolin-4-yI)-dimethyl-amine;
ESI MS m/e 207, M + H+ ; 'H NMR (300 MHz, CDCI3) 5 3.06 (s, 6 H), 6.71 (s, 1 H), 7.45 (ddd, J =
8.4,7.0, 1.2 Hz, I H), 7.63 (ddd, J= 8.4, 6.9, 1.5 Hz, 1 H), 7.91-7.93 (m, 1 H), 7.97-8.03 (m, 1 H).
(4-chloro-quinolin-2-yl)-dimethyl-amine;
ESIMSm/e229,M + Na+;1HNMR(300MHz,CDCl3)63.18(s56H),6.97(brs, 1 H), 7.18-7.31 (m,
1 H), 7.49-7.63 (m, 1 H), 7.66-7.72 (m, 1 H), 7.95-8.00 (m, 1 H).
Step B: Synthesis of Ar2-(cis-4-amino-cyclohexyl)-iV4^V4-dimethyl-quinoline-2,4-diamine.
Using the procedure for the step E of example 1, the title compound was obtained.
FAB MS m/e 285, M + H+ ; ]H NMR (200 MHz, CDC13) 8 1.12-2.00 (m, 9 H), 2.81-2.98 (m, 1 H),
2.93 (s, 6 H), 4.09 (brs, 1 H), 4.75 (d, J= 7.9 Hz, 1 H), 6.03 (s, 1 H), 7.14 (ddd, 7= 8.2, 6.7, 1.3 Hz,
1 H), 7.45 (ddd, J= 8.4, 6.8, 1.5 Hz, 1 H), 7.62 (m, 1 H), 7.84 (dd,/= 8.4, 1.3 Hz, 1 H).
Step C: Synthesis of A'2-[c«-4-(4-bromo-2-trifluoromethoxy-benzyl)-amino-cyclohexyl]-A^^V4-

354
dimethyI-quinoline-2,4-diaminedihydrochloride.
Using the procedure for the step G of example 1, the title compound was obtained.
ESI MS m/e 537, M (free) + H+ ; *H NMR (300 MHz, CDC13) 5 1.73-2.36 (m, 10 H), 3.05-3.31 (m,
2 H), 3.20 (s, 6 H), 4.32 (s, 2 H), 7.30-7.62 (m, 5 H), 7.86 (d, J= 8.6 Hz, 1 H), 8.21 (d, J= 8.4 Hz,
1 H), 8.53-8.64 (m, 1 H), 13.04 (brs, 1 H).
Example 6
Ar2-{cw-4-[2-(4-Bromo-2-trifluoroinethoxy-phenyl)-ethyIaminol-cyclohexyl}-jV4^V4-dimethyl-
quinoline-2,4-diamine dihydrochloride
Step A: Synthesis of 7V2-{ciy-4-[2-(4-bromo-2-trifluoromethoxy-phenyl)-ethylaminol-
cyC1-5hexyIJ-7V4^V4-dimethyl-quinoline-2,4-diamine dihydrochloride.
Using the procedure for the step G of example 1, the title compound was obtained.
ESI MS m/e 551, M (free) + H+ ; 'HNMR (300 MHz, CDC13) 5 1.69-2.40 (m, 10 H), 3.11-3.46 (m,
10 H), 7.26-7.49 (m, 5 H), 7.59 (t, J= 7.3 Hz, 1 H), 7.86 (d, J = 7.5 Hz, 1 H), 8.53-8.70 (m, 1 H),
9.75-10.14 (m, 2 H), 13.05 (brs, 1 H).
Example 7
Ar2-{c/5-4-[(4-Bromo-2-trilluoromethoxy-benzyl)ainino-methyl]-cyclohexyl}-A^^V4-dimethyl-
quinoline-2,4-diamine dihydrochloride
Step A: Synthesis of [cw-4-(4-dimethylamino-quinolin-2-ylamino)-cyclohexylmethyl]-carbamic
acid benzyl ester.
A mixture of (2-chloro-quinolin-4-yl)-dimethyl-amine obtained in step A of example 5 (23.6
g, 114 mmol) and (c/s-4-amino-cyclohexylmethyl)-carbamic acid benzyl ester obtained in step C of
example 3 (36.0 g, 137 mmol) in butanol (31 mL) was stirred at reflux for 14 days. The reaction

355
mixture was poured into saturated aqueous NaHCOs, and the aqueous layer was extracted with CHC13
(three times). The combined organic layer was dried over MgSO4, filtrated, concentrated, and purified
by flash chromatography (NH-silica, 14% to 66% EtOAc in hexane) to give [d5-4-(4-dimethylamino-
quinolin-2-ylamino)-cyclohexyImethyl]-carbamic acid benzyl ester (19.3 g, 39%) as a pale yellow
solid.
ESI MS m/e 433, M + H+ ; 'H NMR (200 MHz, CDC13) 5 1.12-1.97 (m, 9 H), 2.94 (s, 6 H), 3.13 (t,
J= 6.4 Hz, 2 H), 4.06-4.26 (m, 1 H), 4.62-4.94 (m, 2 H), 5.11 (s, 2 H), 6.04 (s, 1 H), 7.14 (ddd, J =
8.4, 7.0, 1.3 Hz, 1 H), 7.29-7.40 (m, 5 H), 7.45 (ddd, J= 8.4, 6.8, 1.5 Hz, 1 H), 7.57-7.64 (m, 1 H),
7.84 (dd,J = 8.4, 1.3 Hz, 1 H).
Step B: Synthesis of A'2-(m-4-aminomethyl-cyclohexyI)-A'4^V4-dimethyl-quinoline-2,4-dianiine.
To a solution of [cis-4-(4-dimethylamino-quinolin-2-ylamino)-cyclohexyImethyl]-
carbamic acid benzyl ester (19.3 g, 44.6 mmol) in MeOH (200 mL) was added 5% Pd/C (1.93 g). The
mixture was stirred at ambient temperature under hydrogen atmosphere for 6 days. The reaction
mixture was filtrated through a pad of celite and concentrated. To a solution of the residue in
methanol (200 mL) was added 10% Pd/C (1.93 g). The mixture was stirred at ambient temperature
under hydrogen atmosphere for 1 day. The reaction mixture was filtrated through a pad of celite,
concentrated, and purified by flash chromatography (silica gel, 5% to 14% 7 M NH3/MeOH in CHCI3)
to giveA^-tc^^-aminomethyl-cyclohexyO-A^/Z-dimethyi-quinoline^^-diamine (12.7 g, 95%) as a
pale yellow solid.
FAB MS m/e 299, M + H+ ; ]H NMR (200 MHz, CDC13) 5 1.08-1.99 (m, 11 H), 2.60 (d, J= 6.2 Hz,
2 H), 2.94 (s, 6 H), 4.04-4.22 (m, 1 H), 4.77-4.93 (m, 1 H), 6.06 (s, 1 H), 7.14 (ddd, 7= 8.4, 7.0, 1.3
Hz, 1 H), 7.45 (ddd, J= 8.4, 6.8, 1.5 Hz, 1 H), 7.61 (m, 1 H), 7.84 (dd,J= 8.4, 1.3 Hz, 1 H).
Step C: Synthesis of 7V2-{cis»4-[(4-bromo-2-trifluoroniethoxy-benzyl)-amino-methyI]-
cyclohexyl}-7V4,/V4-dimethyl-qiiinoline-2,4~diainine dihydrochloride.
Using the procedure for the step G of example 1, the title compound was obtained.
ESIMS m/e 551,M(free) + H+;1HNMR (300MHz, CDC13) 5 1.50-2.20 (m, 9 H), 2.89 (s, 2 H), 3.20

356
(s, 6 H), 3.75-4.02 (m, 1 H), 4.23 (s, 2 H), 7.22-7.32 (m, 2 H), 7.40-7.46 (m, 1 H), 7.49-7.62 (m, 2
H),7.83(d,J=8.7Hz, 1 H), 8.17(d,7= 8.4Hz, 1 H), 8.53-8.69(m, 1 H), 10.05 (brs, 2 H), 13.00(brs,
1H).
Example 8
A^^v-Dimethyl-Ar2-{r/5-4-[(2-trifluoroinethoxy-benzyl)-aniino-methyl]-cyclohexyl}-
quinoline-2,4-diamine dihydrochioride
Step A: Synthesis of /V^-dimethyl-A^-icw^-KZ-trifluoromethoxy-benzyO-amino-methyl]-
cyclohexyl}-quinoline-2,4-diamine dihydrochioride.
Using the procedure for the step G of example 1, the title compound was obtained.
ESI MS m/e 473, M (free) + H* ; !H NMR (300 MHz, CDC13) 5 1.54-2.20 (m, 9 H), 2.87 (brs, 2 H),
3.19 (s, 6 H), 3.70-4.03 (m, 1 H), 4.28 (brs, 2 H), 7.15-7.67 (m, 6 H), 7.81 (d5 J= 8.4 Hz, 1 H), 8.17
(d,J= 7.3 Hz, 1 H), 8.63 (brs, 1 H), 9.92 (brs, 1 H), 13.13 (s, 1 H).
Example 9
A^-f c«-4-(4-Bromo-2-trifluoromethoxy-benzyl)amino-cyclohexyl]-7V4-methy 1-5,6,7,8-
tetrahydro-quinazoline-2T4-diamine dihydrochioride
Step A: Synthesis of 5,6,7,8-tetrahydro-quinazoline-2,4-diol.
To a solution of 2-oxo-cyclohexanecarboxylic acid ethyl ester (61.5 g, 361 mmol) in EtOH
(61.5 mL) was added urea (73.8 g, 1.23 mol). The mixture was stirred at reflux for 10.5 days and
stirred at ambient temperature for 30 min. The precipitate was filtrated, washed with acetone, and
dried. A suspension ofthe above solid in H2O(100 mL) stirred on an ice-bath for 1 hr. The precipitate
was filtrated, washed with hexane, and dried under reduced pressure to give 5,6,7,8-tetrahydro-
quinazoline-2,4-diol (21.0 g, 35%) as a pale yellow solid.

357
CI MS m/e 167, M + H+ ; *H NMR (300 MHz, DMSO-d6) 5 1.48-1.71 (m, 4 H), 2.09-2.19 (m, 2 H),
2.24-2.34 (m, 2 H), 10.41-10.98 (m, 2 H).
Step B: Synthesis of 2,4-dichloro-5,6,7,8-tetrahydro-quinazoline.
Using the procedure for the step A of example 1, the title compound was obtained.
ESI MS m/e 203, M+ ; !H NMR (300 MHz, CDCI3) 8 1.83-1.94 (m, 4 H), 2.67-2.79 (m, 2 H),
2.84-2.95 (m, 2 H).
Step C: Synthesis of (2-chloro-5,6,7T8-tetrahydro-quinazolin-4-yl)-methyl-amine.
To a solution of 2,4-dichloro-5,6,7,8-tetrahydro-quinazoIin (8.70 g, 42.8 mmol) in THF (87
mL) was added 40% aqueous MeNH2 (8.32 g, 107 mmol). The mixture was stirred at ambient
temperature for 8 hr. The solution was poured into saturated aqueous NaHCO3 and the aqueous layer
was extracted with CHC13 (three times). The combined organic layer was dried over MgSO4, filtrated,
concentrated, and purified by flash chromatography (NH-silica, 50% EtOAc in hexane) to give
(2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yI)-methyl-amine (7.04 g, 83%) as a white solid.
ESI MS m/e 220, M + Na+ ; !H NMR (300 MHz, CDC13) 5 1.74-1.92 (m, 4 H), 2.26 (t, J = 5.5 Hz, 2
H), 2.67 (t,J=5.6Hz,2H),3.05(d,y=5.0Hz,3H), 4.81 (s, 1 H).
Step D: Synthesis of ^-(c/s^-amino-cyclohexyty-iV^methyl-S^^S-tetrahydro-quinazoline-
2,4-diamine.
Using the procedure for the step E of example 1, the title compound was obtained.
ESI MS m/e 276, M + H+ ; *H NMR (300 MHz, DMSO-d6) 5 1.33-1.76 (m, 12 H), 2.11-2.21 (m, 2
H), 2.31-2.40 (m, 2 H), 2.70-2.77 (m, 2 H), 2.78 (d, J = 4.5 Hz, 3 H), 3.71-3.83 (m, 1 H), 5.50-5.63
(m, 1 H), 6.10-6.22 (m, 1 H).
Step E: Synthesis of Ar2-[c«-4-(4-bromo-2-trifluoromethoxy-benzyl)-amino-cyclohexyI]-7V4-
methyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine dihydrochloride.
Using the procedure for the step G of example 1, the title compound was obtained.

358
ESI MS m/e 528, M (free) + H*; lR NMR (300 MHz, CDC13) 5 1.66-2.24 (m, 12 H), 2.41-2.56 (m,
4 H), 3.00 (d, J= 4.5 Hz, 3 H), 3.04 (brs, 1 H), 4.03 (brs, 1 H), 4.30 (brs, 2 H), 7.45-7.48 (m, I H),
7.52(dd,J=8.3,1.8Hz, 1 H), 7.61 (d,J = 5.8 Hz, 1 H), 7.74 (brs, 1 H), 8.14 (d, J= 8.2 Hz, 1 H),
11.84 (brs, 1 H).
Example 10
Ar2-{cw-4-[2-(4-Bromo-2-trifluoromethoxy-phenyl)-ethyIamino]-cyclohexyl}-V-methyl-S,6,7,8-
tetrahydro-quinazoline-2,4-diamine dihydrochloride
Step A: Synthesis of JV2-{c/,y-4-[2-(4-bromo-2-trifluoromethoxy-phenyI)-ethylamino]-
cyclohexyl}-A^-methyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine dihydrochloride.
Using the procedure for the step G of example 1, the title compound was obtained.
ESI MS m/e 542, M (free) + }T ; ]H NMR (300 MHz, CDC13) 5 1.57-2.25 (m, 12 H), 2.35-2.60 (m,
4 H), 2.94-3.28 (m, 6 H), 3.32-3.45 (m, 2 H), 4.13 (brs, 1 H), 7.30-7.51 (m, 4 H), 7.72 (d, J= 6.2 Hz,
1 H), 9.86 (brs, 2 H) 11.90 (s, 1 H).
Example 11
A^-{c/y-4-[(4-Bromo-2-trifluoromethoxy-benzyl)amino-methyl]-cyclohexyIJ-A^-methyl-5,6,7,8-
tetrahydro-quinazoline-2,4-diamine dihydrochloride
Step A: Synthesis of [c«-4-(4-methylamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-
cyclohexylm ethyl ]-carbamic acid benzyl ester.
A mixture of (2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yl)-methyl-amine obtained in step C
of example 9 (2.00 g, 10.1 mmol) and (as-4-amino-cyclohexylmethyI)-carbamic acid benzyl ester
obtained in step C of example 3 (3.19 g, 12.2 mmol) in butanol (3 mL) was stirred at 130 °C for 16 hr
in a sealed tube. The reaction mixture was poured into saturated aqueous NaHCO3, and the aqueous

359
layer was extracted with CHCI3 (three times). The combined organic layer was dried over MgSO4,
filtrated, concentrated, and purified by flash chromatography (silica gel, 10% MeOH in CHCI3) to
give [c«-4-(4-methylamino-5,6,7,8-tetrahydro-quinazolin-2-yIamino)-cyclohexylmethyl]-carbamic
acid benzyl ester (1.38 g, 32%) as a pale yellow oil.
ESI MS m/e 424, M + H+ ; ]H NMR (300 MHz, CDCI3) 8 1.31-2.02 (m, 13 H), 2.22-2.34 (m, 2 H),
2.52-2.64 (m, 2 H),3.05 (d,J = 4.8 Hz, 3 H), 3.11 (t, J= 6.1 Hz, 2 H), 5.05-5.23 (m, 1 H), 5.08 (s, 2
H), 6.34-6.47 (m, 1 H), 7.23-7.42 (m, 5 H), 7.99 (d, ./ = 7.3 Hz, 1 H), 12.34 (brs, 1 H).
Step B: Synthesis of Ar2-{c/5-4-[(4-bromo-2-trifluoromethoxy-benzyl)-aniino-methyl]-
cyclohexylJ-A^-methyl-S^^jS-tetrahydro-quinazoline^^-diaminedihydrochloride.
Using the procedure for the step E of example 3, the title compound was obtained.
ESI MS m/e 542, M (free) + it; ]H NMR (200 MHz, CDC13) 5 1.50-2.19 (m, 13 H), 2.58-2.61 (m,
2 H), 2.72-2.91 (m, 2 H), 2.83-2.97 (m, 2 H), 3.24 (s, 6 H), 4.15-4.20 (m, 1 H), 4.22-4.38 (m, 2 H),
7.43-7.50 (m, 1 H), 7.56-7.61 (m, 1 H), 8.18-8.29 (m, 2 H), 10.06 (brs, 2 H), 12.30 (brs, 1 H).
Example 12
A^-Methyl-^-lm-^KI-trifluoromethoxy-benzylJ-amino-niethylj-cyclohexylJ-S^,?^-
tetrahydro-quinazoIine-2,4-diamine dihydrochloride
Step A: Synthesis of Art-methyl-A^2-{c/$-4-[(2-trifluoromethoxy-benzyl)-aniino-methyI]-
cyclohexyl}-5,6,7,8-tetrahydro-quinazoline~2,4-diamine dihydrochloride.
Using the procedure for the step G of example 1, the title compound was obtained.
ESI MS m/e 464, M (free) + H+ ; !H NMR (300 MHz, DMSO-d6) 6 1.28-2.04 (m, 15 H), 2.14-2.30 (m,
2 H), 2.83-2.95 (m, 2 H), 2.91 (d, J = 4.5 Hz, 3 H), 4.13 (brs, 1 H), 4.22 (brs, 2 H), 7.43-7.62 (m, 3
H), 7.91 (dd,J= 7.5, 1.6 Hz, 1 H), 8.09 (d,J= 6.7 Hz, 2 H), 9.37 (brs, 2 H), 12.30-12.70 (m, 1 H).

360
Example 13
iV2-[m-4-(4-Bromo-2-trifluoromethoxy-benzyl)-amino-cyC1-5hexyl]-iV4^V4-dimethyl-
5,6,7,8-tetrahydro-quinazoline-2,4-diaminedihydrochIoride
Step A: Synthesis of (2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yl)-dimethyl-amine.
To a solution of 2,4-dichloro-5,6,7,8-tetrahydro-quinazolin (7.00 g, 34.5 mmol) in THF (70
mL) was added 50% aqueous MeNH2 (7.77 g, 86.2 mmol). The mixture was stirred at ambient
temperature for 2.25 hr. The solution was poured into saturated aqueous NaHCO3 and the aqueous
layer was extracted with CHC13 (three times). The combined organic layer was dried over MgSO4,
filtrated, concentrated, and purified by flash chromatography (NH-silica, 20% EtOAc in hexane) to
give (2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yl)-dimethyl-amine (6.08 g, 83%) as a white solid.
ESI MS m/e 234, M + Na+ ; *H NMR (300 MHz, CDC13) 5 1.62-1.90 (m, 4 H), 2.59 (t, J = 6.0 Hz, 2
H), 2.76 (t, J= 6.6 Hz, 2 H), 3.06 (s, 6 H).
Step B: Synthesis of 7V2-( ci5-4-aniino-cyclohesyl)-A^^V4-dimethyl-5,6,7,8-tetrahydro-
qtiinazoHne-2,4-diamine.
Using the procedure for the step E of example 1, the title compound was obtained.
FAB MS m/e 290, M + H+ ; !HNMR (200 MHz, CDC13) 6 0.95-1.94 (m, 14 H), 2.49 (t, J= 5.9 Hz,
2 H), 2.61 (t, J = 7.0 Hz, 2 H), 2.72-2.94 (m, I H), 2.94 (s, 6 H), 3.89-4.11 (m, 1 H), 4.73 (d, J = 7.5
Hz, 1 H).
Step C: Synthesis of Ar2-[c/$-4-(4-bromo-2-trifluoromethoxy-benzyl)-amino-cyclohexyl]-
A^^-dimethyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine-dihydrochloride.
Using the procedure for the step G of example 1, the title compound was obtained.
ESI MS m/e 542, M (free) + H+ ; 'HNMR (300 MHz, CDC13) 5 1.57-2.32 (m, 12 H), 2.52-2.60 (m,
2 H), 2.63-2.72 (m, 2 H), 3.11-3.24 (m, 7 H), 4.12-4.23 (m, 1 H), 4.28 (s, 2 H), 7.41 (d, J= 10.4 Hz,
1 H), 7.49 (dd,y= 8.2, 1.9 Hz, 1 H), 8.19 (d, J= 8.4 Hz, 1 H), 8.25 (d,J= 8.1 Hz, 1 H), 10.02 (brs,
1 H), 12.43 (brs, 1 H).

361
Example 14
A^2-{c«-4-[2-(4-Bromo-2-trifluoromethoxy-phenyl)-ethylamino)-cyclohexyI}-7V1^V4-dimethyl-5,
6,7,8-tetrahydro-quinazoIine-2,4-diaminedihydrochIoride
Step A: Synthesis of 7V2-{cis-4-[2-(4-bromo-2-trifluoromethoxy-phenyl)-ethylamino]-
cyclohexyl}-Ar*^Vt-dimethyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine- dihydrochloride.
Using the procedure for the step G of example 1, the title compound was obtained.
ESI MS m/e 556, M (free) + H+ ; *H NMR (300 MHz, CDCI3) 5 1.57-2.32 (m, 12 H), 2.56 (t, J = 5.8
Hz, 2 H), 2.69 (t, J= 6.2 Hz, 2 H), 3.14-3.41 (m, 9 H), 4.13-4.25 (m, 1 H), 7.35-7.44 (m, 2 H),
7.49-7.55 (m, 1 H), 8.20 (d, J= 7.8 Hz, 1 H).
Example 15
Ar2-{C1-5-4-I(4-Bromo-2-trifluoromethoxy-benzyl)-amino-methyl]-cyclohexyI}-Ar'>/V4-diinethyl-
5,6,7,8-tetrahydro-quinazoline-2,4-diamine dihydrochloride
Step A: Synthesis of [c/$-4-(4-dimethylamino-quinolin-2-ylamino)-cyC1-5hexylmethyl]-carbamic
acid benzyl ester.
Using the procedure for the step A of example 11, the title compound was obtained.
ESIMSm/e438,M + H+;1HNMR(300MHz,CDCl3)5 1.18-1.39 (m, 2 H), 1.48-1.94 (m, 11 H),
2.49 (t,J= 5.9 Hz, 2 H), 2.60 (t, J= 6.6 Hz, 2 H), 2.94 (s, 6 H), 3.09 (t, J= 6.1 Hz, 2 H), 4.01-4.13
(m, 1 H), 4.70-4.91 (m, 2 H), 5.09 (s, 2 H), 7.27-7.39 (m, 5 H).
Step B: Synthesis of A^"-{c/s-4-[(4-bromo-2-trifluoromethoxy-benzyl)-aniino-niethyI]-
cyclohexyl}-Ar'^V4-dimethyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine dihydrochloride.
Using the procedure for the step E of example 3, the title compound was obtained.

362
ESI MS m/e 556, M (free)+ H+;'HNMR (300 MHz, CDC13) 5 1.46-2.17 (m, 12 H), 2.55 (t, .7=5.8
Hz, 2 H), 2.69 (t,7= 6.1 Hz, 2 H), 2.79-2.92 (m, 2 H), 3.20 (s, 6 H), 4.08-4.18 (m, 1 H), 4.20-4.31 (m,
2 H), 7.43-7.47 (m, 1 H), 7.53 (dd, 7= 8.4, 1.9 Hz, 1 H), 8.16 (d, .7= 7.8 Hz, 1 H), 8.22 (d, J= 8.4
Hz, 1 H), 10.02 (brs, 2 H), 12.28 (brs, 1 H).
Example 16
7V4^V4-Dimethyl-A^2-{c/5-4-[(2-trifluoromethoxy-benzyl)-amino-methyl]-cyclohexyI}-5,6,7,8-
tetrahydro-quinazoline-2,4-diamine dihydrochloride
Step A: Synthesis of 7V4^V4-dimethyl-7\^-{c/y-4-[(2-trifluoromethoxy-benzyl)-amino-
methyl]-cyclohexyl}-5,6,7T8-tetrahydro-quinazoline-2,4-diamine dihydrochloride.
Using the procedure for the step G of example 1, the title compound was obtained.
ESI MS m/e 478, M (free) + H+ ; 'HNMR (300 MHz, CDC13) 5 1.48-2.15 (m, 13 H), 2.55 (t, J= 5.4
Hz, 2 H), 2.71 (t, J= 6.2 Hz, 2 H)? 2.77-2.89 (m, 2 H), 3.19 (s, 6 H), 4.10 (brs, 1 H), 4.26-4.37 (m, 2
H), 7.27-7.34 (m, 1 H), 7.36-7.47 (m, 2 H), 8.15-8.25 (m, 2 H), 9.90 (s, 2 H), 12.52 (s, 1 H).
Example 17
iV2-[ci5-4-(4-Bromo-2-trifluoromethoxy-benzyl)-amino-cyclohexyl]-7V4^V4-dimethyl-pyrimidin-
2,4-diamine dihydrochloride
Step A: Synthesis of [cw-4-(4-bromo-2-trifluoromethoxy-benzyl)-amino-cyclohexyl]-carbamic
acid tert-buty\ ester.
To a solution of (ds-4-amino-cyctohexy!)-carbamic acid /err-butyl ester obtained in step D of
example 1 (6.72 g, 31.4 mmol) in CHCI3 (67 mL) were added 4-bromo-2-trifluoromethoxy-
benzaldehyde obtained in step F of example 1 (8.44 g, 31.4 mmol), acetic acid (1.88 g, 31.3 mmol),
and NaBH(OAc)3 (9.97 g, 47.0 mmol). The reaction mixture was stirred at ambient temperature for

363
4 hr. The reaction was quenched with saturated aqueous NaHCO3 and the aqueous layer was extracted
with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtrated, concentrated,
and purified by flash chromatography (silica gel, 33% EtOAc in hexane) to give [cw-4-(4-bromo-
2-trifluoromethoxy-benzyl)-amino-cyclohexyl]-carbamic acid tert-buty\ ester (10.28 g, 70%) as a pale
yellow oil.
ESI MS m/e 467, M + H+ ; 'H NMR (300 MHz, CDC13) 8 1.16-1.78 (m, 17 H), 2.57-2.70 (m, 1 H),
3.62 (brs, 1 H), 3.78 (s, 2 H), 4.60 (brs, 1 H), 7.34-7.54 (m, 3 H).
Step B: Synthesis of (2-chloro-pyrimidin-4-yl)-dimethyl-amine.
To a solution of 2,4-dichIoro-pyrimidine (15.0 g, 10.15 mmol) in THF (150 mL) was added
50% aqueous MeNH2 (22.7 g, 25.2 mmol). The mixture was stirred at ambient temperature for 2 hr.
The solution was poured into saturated aqueous NaHCO3 and the aqueous layer was extracted with
CHCI3 (three times). The combined organic layer was dried over MgSO4, filtrated, concentrated, and
purified by flash chromatography (NH-siHca, 20% EtOAc in hexane) to give (2-chloro-
pyrimidin-4-yI)-dimethyl-amine (8.66 g, 55%) as a white solid and (4-chloro-pyrimidin-2-yI)-
dimethyl-amine (0.87 g, 6%) as a white solid.
(2-chloro-pyrimidin-4-y!)-dimethyI-amine;
CI MS m/e 158, M + H+ ; 'H NMR (300 MHz, CDC13) 8 3.12 (s, 6 H), 6.32 (d, J= 6.1 Hz, 1 H), 8.00
(d,7=6.1 Hz, 1 H).
(4-ch lor o-pyr im id in-2-y l)-d imethy I-am ine;
ESI MS m/e 157, M+; !HNMR (300 MHz, CDC13) 8 3.21 (s, 6 H), 6.50 (d, 7 = 5.1 Hz, 1 H), 8.18 (d,
7=5.1 Hz, 1 H).
Step C: Synthesis of iV2-(c/s-4-(4-bromo-2-trinuoromethoxy-benzyl)-amino-cyclohexyl]-
Arl^V4-dimethyl-pyrimidine-2,4-diaminedihydrochloride.
To a solution of [cw-4-(4-bromo-2-trifluoromethoxy-benzylarnino)-cyclohexyl]-
carbamic acid tert-buty\ ester (3.00 g, 6.42 mmol) in EtOAc (30 mL) was added 4 M hydrogen
chloride in EtOAc (60 mL). The reaction mixture was stirred at ambient temperature for 1 hr and

364
concentrated. The residue was alkalized with saturated aqueous NaHCO3. The aqueous layer was
extracted with CHC13 (three times). The combined organic layer was dried over MgSO4, filtrated, and
concentrated. The above material (466 mg, 1.27 mmol) and (2-chIoro-pyrimidin-4-yl)-
dimethyl-amine (200 mg, 1.27 mmol) in butanol (1 mL) was stirred at 130 °C for 13.5 hr in a sealed
tube. The reaction mixture was poured into saturated aqueous NaHCC>3 and the aqueous layer was
extracted with CHC13 (three times). The combined organic layer was dried over MgSO4, filtrated,
concentrated, and purified by medium-pressure liquid chromatography (NH-silica, 20% EtOAc in
hexane) to give a colorless oil. To a solution of the above oil in EtOAc (2 mL) was added 4 M
hydrogen chloride in EtOAc (5 mL). The mixture was stirred at ambient temperature for 1 hr and
concentrated. A suspension of the residue in Et2O (12 mL) was stirred at ambient tempareture for 1
hr. The precipitate was collected by filtration, washed with Et2O, and dried under reduced pressure to
7V2-[cz\si-4-(4-bromo-2-trifluoromethoxy-benzyl)-amino-cyclohexyl]-Vv ,7v-dimethyl-pyrimidine-2,4-
diamine dihydrochloride (180 mg, 25%) as a white solid.
EST MS m/e 488, M (free) + H+ ; ]H NMR (300 MHz, CDC13) 5 1.54-1.72 (m, 2 H), 2.01-2.29 (m, 6
H), 3.02 (brs, 1 H), 3.16 (s, 3 H), 3.24 (s, 3 H), 4.13 (brs, 1 H), 4.30 (s, 2 H), 6.02 (d, J= 7.5 Hz, 1
H), 7.40-7.43 (m, 1 H), 7.50 (dd, J= 8.4, 1.9 Hz, 1 H), 7.99 (d, 7= 7.3 Hz, 1 H), 8.26 (d, J= 8.4 Hz,
1 H), 8.57 (d, J= 7.0 Hz, 1 H), 10.25 (s, 2 H).
Example 18
Ar2-{C1-5-4-[2-(4-Bromo-2-trifluoromethoxy-phenyI)-ethyIa mi no]-cyclohexyl}-7V4^V4-di methyl-
pyrimidine-2,4-diamine dihydrochloride
Step A: Synthesis of [c/$-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-carbamic acid
/erf-butyl ester.
A mixture of (2-chloro-pyrimidm-4-yI)-dimethyl-amine obtained in step B of example 17
(1.50 g, 9.52 mmol) and (c/s-4-amino-cyclohexyl)-carbamic acid rerr-butyl ester obtained in step D of
example 1 (2.24 g, 10.5 mmol) in IPA (1.5 mL) was stirred at 130 °C for 22 hr in a sealed tube. The

365
reaction mixture was poured into saturated aqueous NaHCO3, and the aqueous layer was extracted
with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtrated, concentrated,
and purified by medium-pressure liquid chromatography (NH-silica, 10% EtOAc in hexane) to give
[c/5-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-carbamic acid /err-butyl ester (1.34 g,
42%) as a white solid.
ESI MS m/e 358, M + Na+ ; :H NMR (300 MHz, CDCI3) 5 1.45 (s, 9 H), 1.48 (s, 8 H), 3.03 (s, 6 H),
3.61 (brs, 1 H), 3.89-4.04 (m, 1 H), 4.47-4.63 (m, 1 H),4.77-4.89 (m, 1 H), 5.80 (d, J-6.1 Hz, 1 H),
7.84 (d, 7=6.1 Hz, 1 H).
Step B: Synthesis of A^-fcw-^amino-cyC1-5hexyty-A^^-dimethyl-pyrimidine^^-diainine.
To a solution of [cw-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-
carbamic acid ferf-butyl ester (1.26 g, 3.76 mmol) in EtOAc (15 mL) was added 4 M hydrogen
chloride in EtOAc (15 mL). The reaction mixture was stirred at ambient temperature for 1 hr and
concentrated. The residue was alkalized with 1 M aqueous NaOH. The aqueous layer was extracted
with CHCI3 (six times). The combined organic layer was dried over MgSOj, filtrated, and
concentrated to give N -( cw^-amino-cyC1-5hexy^-A/4^-dimethyl-pyrimidine-2,4-diamine(923 mg,
quant.) as a pale yellow oil.
ESI MS m/e 250, M+ H+;!HNMR (300 MHz, CDC13) 5 1.29-1.51 (m, 2 H), 1.61-1.91 (m, 6 H),
2.80-2.92 (m, 1 H), 3.03 (s, 6 H), 3.96-4.04 (m, 1 H), 4.85-4.98 (m, 1 H), 5.79 (d, J = 6.1 Hz, 1 H),
7.84 (d, 7=6.1 Hz, 1 H).
Step C: Synthesis of iV2-{c/s-4-[2-(4-bromo-2-trifluoromethoxy-phenyl)-ethylamino]-
cyclohexyl}-7V4^V4-dimethyl-pyrimidine-2,4-diaminedihydrochloride.
Using the procedure for the step G of example 1, the title compound was obtained.
ESI MS m/e 502, M (free) + H+ ; lHNMR (300 MHz, CDC13) 5 1.62-1.82 (m, 2 H), 1.97-2.44 (m, 6
H), 3.16 (s, 3 H), 3.14-3.31 (m, 1 H), 3.25 (s, 3 H), 3.34-3.46 (m, 2 H), 4.18 (brs, 1 H), 6.02 (d,J =
6.8 Hz, 1 H), 7.34-7.43 (m, 2 H), 7.45-7.52 (m, 1 H), 7.85-7.97 (m, 1 H), 8.49-8.59 (m, 1 H), 9.95 (brs,
2H), 12.42 (brs, 1 H).

366
Example 19
Ar2-{c/.y-4-[(4-Bromo-2-trifluoromethoxy-benzyl)-amino-methyl]-cyclohexylJ-Arl^V4-dimethyl-
pyrimidine-2,4-dianiinedihydrochloride
Step A: Synthesis of [ro-4-(4-dimethylamino-pyrimidin-2-yIainino)-cyclohexylmethyl]-
carbamic acid benzyl ester.
A mixture of (2-chloro-pyrirnidin-4-yl)-dimethyI-arnine obtained in step B of example 17
(1.50 g, 9.52 mmol) and c/s-(4-amino-cyclohexylmethyl)-carbamic acid benzyl ester (2.75 g, 10.5
mmol) in IPA (1.5 tnL) was stirred at 130 °C for 22 hr in a sealed tube. The reaction mixture was
poured into saturated aqueous NaHCO3, and the aqueous layer was extracted with CHC13 (three times).
The combined organic layer was dried over MgSO4, filtrated, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica, 10% EtOAc in hexane to EtOAc) to give
[c*"5-4-(4-dimethylamino-pyrimidin-2-ylamino)-
cyclohexylmethyl]-carbamic acid benzyl ester (816 mg, 22%) as a pale yellow oil.
ESI MS m/e 406, M + Na+ ; 'HNMR(300 MHZ, CDC13) 5 1.22-1.92 (m, 9 H), 3.03 (s, 6 H), 3.11 (t,
J= 6.2 Hz, 2 H), 4.02-4.15 (m, 1 H), 4.82-4.93 (m, 2 H), 5.10 (s, 2 H), 5.79 (d, J= 6.1 Hz, 1 H),
7.28-7.42 (m, 5 H), 7.83 (d, J= 6.1 Hz, 1 H).
Step B: Synthesis of iV2-(cw-4-aminomethyl-cyclohexyI)-7V4^V4-dimethyl-pyrimidine-2,4-
diamine.
Using the procedure for the step B of example 7, the title compound was obtained.
ESI MS m/e 250, M + H+ ; lH NMR (300 MHz, CDCI3) 5 1.40-1.88 (m, 9 H), 2.87 (d, J= 5.9 Hz, 2
H), 3.03 (s, 6 H), 4.11 (bis, 1 H), 5.63 (bis, I H), 5.78 (d, J= 6.2 Hz, 1 H), 7.08 (brs, 2 H), 7.82 (d,
.7=6.2 Hz, 1H).
Step C: Synthesis of Ar2-{e/5-4-[(4-bromo-2-trifluoromethoxy-benzyl)-amino-methyl]-

367
cyclohexyl}-V^-dimethyl-pyrimidine-2,4-diamine dihydrochloride.
Using the procedure for the step G of example 1, the title compound was obtained.
ESI MS m/e 502, M (free) + H+ ; !H NMR (300 MHz, CDCI3) 6 1.52-2.21 (m, 9 H), 2.85 (d, J= 5.8
Hz, 2 H), 3.16 (s, 3 H), 3.24 (s, 3 H), 4.15-4.30 (m, 3 H), 6.00 (d, J= 7.6 Hz, 1 H), 7.43-7.47 (m, 1
H), 7.53 (dd, J= 8.3,1.9 Hz, 1 H), 7.66 (d, J= 7.5 Hz, 1 H), 8.20 (d,J= 8.4 Hz, I H), 8.53 (d, J= 7.5
Hz, 1 H), 10.07 (brs, 2 H).
Example 20-672
To a solution of poly(4-vinylpyridine) (75 pL) in CH2CI2 (200 pL) were added the amines (30
pmol) as shown below in CH2C12 (200 pL) and acid chloride (60 pmol) in CH2C12 (200 pL) at ambient
temperature. After stirring at the same temperature for 19 hr, the reaction mixture was filtrated and
concentrated by a stream of dry N2- To the residue were added dry CH2C12 (700 pL) and PSA (300
pL). After the stirring at ambient temperature for 14 hr, the reaction mixture was purified by silica gel
chromatography (NH-silica, 50% EtOAc in hexane to EtOAc only) to give the desired product. The
product was determined by ES1-MS or APCI-MS.
Wherein the amines are selected from
jV2-(c/5-4-amino-cyclohexyl)-iv JT-dimethyl-quinoline-2,4-diamine obtained in step B of example 5,
7V2-fc/5-4-aminomethyl-cyclohexyI)-7V4:fA'4-dimethyl-quinoline-2,4-diamine obtained in step B of
example 7, AT -(crw^-amino-cyC1-5hexy^-A^^-dimethyl-S^^^-tetrahydro-quinazoline^^-diamine
obtained in step B of example 13, jV2-(cz'5-4-aminomethyl-cyclohexyl)-A^//-dimethyl-5,6,7,8-
tetrahydro-quinazoline-2,4-diamine obtained in intermediate of step B of example 15, N2-(cis-4-
amino-cyclohexyl)-7v ,A* -dimethyI-pyrirnidine-2,4-diamine obtained in stepB of example 18, or
7V2-(c/5-4-aminomethyI-cyclohexyl)-7V4^V4-dimethyI-pyrimidine-2,4-diamine obtained in step B of
example 19.

368
Example 673-1084
To a solution of l-cyclohexyl-3-methylpolystyrene-carbodiimide (150 |iL) in CH2C12 (400
\xL) were added the amines (30 umol) as shown below in CH2C12 (200 uX) and carboxyiic acid (60
Hinol) in CH2CI2 (200 jiL) at ambient temperature. After stirring at the same temperature for 20 hr, the
reaction mixture was filtrated through NH-silica gel, concentrated by a stream of dry N2, and purified
by silica gel chromatography (silica gel, 2% to 7% 2 M NH3/MeOH in CHC13) to give the desired
product. The product was determined by ESI-MS or APCI-MS.
Wherein the amines are selected from
N2-( cw^-amino-cyclohexyiyV^-dimethyl-quinoIine^^-diamine obtained in step B of example 5,
JV2-( c/5-4-aminomethyl-cyclohexyl)-N4,7V4-dimethyl-quinoline-2,4-diamine obtained in step B of
example 1, N2-{ c/5-4-amino-cyclohexyl)-7V4^V4-dimethyl-5,6,7,8-tetrahydro-quinazoline-2?4-diamine
obtained in step B of example 13, N2-{ c*5-4-aminomethyl-cyclohexyl)-V,A^-dimethyI-5,6,7,8-
tetrahydro-quinazoline-2,4-diamine obtained in intermediate of step B of example 15, N2-( cis-
4-amino-cyclohexyI)-A^4^V4-dimethyl-pyrimidine-2,4-diamine obtained in step B of example 18, or
N2-( c/5-4-aminomethyl-cyclohexyl)-N4?iV4-dimethyl-pyrimidine-2,4-diamine obtained in step B of
example 19.
Example 1085-1446
-method A-
To a solution of the amines (36 \imo\) as shown below in MeOH (200 \iL) were added
aromatic aldehyde (30 p.mol) in MeOH (200 (J.L) and AcOH (90 fimol) at ambient temperature. The
reaction mixture was stirred at the same temperature for 1 hr. To the mixture was added NaBH3CN
(120 j^mol) in MeOH (200 ^iL). After stirring at the same temperature for 20 hr, the reaction mixture
was concentrated by a stream of dry N2. The residue was partitionated between CHCI3 and 2 M
aqueous sodium hydroxide. The aqueous layer was extracted with CHC13 (500 |^L) and EtOAc (300
^L). The combined organic layers were dried over MgSO4, concentrated by a stream of dry N2, and

369
purified by silica gel chromatography (silica gel, 2% to 7% 2 M NH3/Me0H in CHC13) to give the
desired product. The product was determined by ESI-MS or APCI-MS.
-method B-
To a solution of the amines (36 umol) as shown below in MeOH (200 (aL) were added
aliphatic aldehyde (30 jimol) in MeOH (200 ^L), AcOH (90 jimol), and NaBH3CN (120 jimol) in
MeOH (200 \iL) at ambient temperature. After stirring at the same temperature for 20 hr, the reaction
mixture was concentrated by a stream of dry N2. The residue was partitionated between CHCI3 and
2 M aqueous sodium hydroxide. The aqueous layer was extracted with CHCI3 (500 (oL) and EtOAc
(300 ^L). The combined organic layers were dried over MgSO4, concentrated by a stream of dry N2,
and purified by silica gei chromatography (silica gel, 2% to 7% 2 M NH3/MeOH in CHC13) to give the
desired product. The product was determined by ESI-MS or APCI-MS.
Wherein the amines are selected from
N2-( ci5-4-amino-cyclohexyl)-A^^V4-dimethyl-quinoline-2,4-diamine obtained in step B of example 5,
N2-( cw-4-aminomethyl-cyclohexyl)-iV4^V4-dimethyl-quinoline-2,4-diamine obtained in step B of
example 1 ,N2-{ c/5-4~amino-cyC1-5hexyl)-A'4^V4-dimethyl-5,6,7,8-tetrahydro-quinazoIine-2,4-diamine
obtained in step B of example 13, JV2-( aV4-aminomethyl-cyclohexyi)-A^^Hdimethyl-5,6,758-
tetrahydro-quinazoline-2,4-diamine obtained in intermediate of step B of example 15, N -( cis-4-
amino-cyC1-5hexyl)-A'4JV4-dimethyl-pyrimidine-2,4-diamine obtained in step B of example 18, or
N2-( c/5-4-aminomethyl-cyclohexy!)-A'4^V4-dimethy!-pyrimidine-2,4-diamine obtained in step B of
example 19.
Example 1457-1462,1478-1480,1491-1497, and 1510-1512
To a solution of the amide product in THF (200 \x\) was added 1 M borane-THF complex in
THF (300 fxl, 300 jimol). The mixture was stirred at 80 °C for 1 hr, and concentrated by a stream of
dry N2. To the residue were added 1 M aqueous HC1 (300 \xl) and THF (200 [i\). The mixture was
stirred at 80 °C for 1 hr and concentrated by a stream of dry N2. To the residue was partitionated

370
between CHCI3 and 2 M aqueous sodium hydroxide. The aqueous layer was extracted with CHCI3
(300 |_iL, twice) and EtOAc (300 ^L). The combined organic layers were dried over MgSO4,
concentrated by a stream of dry N2, and the purified by silica gel chromatography (silica gel, 2% to 7%
2 M NH3/MeOH in CHCI3) to give the desired product. The product was determined by ESI-MS or
APCI-MS.
Example 1447-1456,1463-1477,1481-1490,1498-1509, and 1513-1538
To a suspension of Dess-Martin periodinane (63 p.mol) in CH2CI2 (200 f^L) was added
alcohol (35 (imol) in CH2C12 (200 \xL) at ambient temperature, and the reaction mixture was stirred at
the same temperature for 18 hr. To the reaction mixture were added amines (36 fimol) as shown below
in MeOH (200 u,L) and AcOH (90 \xh). The mixture was stirred at the same temperature for 1 hr, and
then NaBH3CN (120 p.mol) in MeOH (200 ^L) was added. After stirring at the same temperature for
17 hr, the reaction mixture was concentrated by a stream of dry N2- The residue was partitionated
between CHC13 and 2 M aqueous sodium hydroxide. The aqueous layer was extracted with CHC13
(500 mL) and EtOAc (300 \xL). The combined organic layers were dried over MgSO4, concentrated
by a stream of dry N2, and purified by silica gel chromatography (silica gel, 2% to 7% 2 M NH3/MeOH
in CHCI3) to give the desired product. The product was determined by ESI-MS or APCI-MS.
Wherein the amines are selected from
N~-( ci^-amino-cyclohexyl)-^^-dimethyI-quinoline-2,4-diamine obtained in step B of example 5,
N2-( cw-4-aminomethyl-cyclohexyl)-7V4^V4-dimethyl-quinoline-2,4-diamine obtained in step B of
example 7, JV -( c/5-4-amino-cyclohexy!)-i\rrA^-dimethyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine
obtained in stepB of example 13, Af~-( c/5-4-aminomethyl-cyclohexyl)-A^Jv-dimethyl-5,6,7,8-
tetrahydro-quinazoline-2,4-diamine obtained in intermediate of step B of example 15, N2-( cis-4-
amino-cyclohexyl)-A^,V-dimethyl-pyrimidine-2,4-diamine obtained in step B of example 18, or
N -( c/5-4-aminomethyl-cyclohexyI)-A^:/r-dimethyl-pyrimidine-2,4-diamine obtained in step B of
example 19.

371
Example 1539-1658
To a solution of poly(4-vinylpyridine) (75 |aL) in CH2C12 (200 \iL) were added the amines (30
I^mol) as shown below in CH2CI2 (200 pL) and chloroformate (60 ^mol) in CH2CI2 (200 pL) at
ambient temperature. After stirring at the same temperature for 17 hr, the reaction mixture was
filtrated and concentrated by a stream of dry N2. To the residue were added CH2C12 (700 ^L) and PSA
(300 jaL). After the stirring at ambient temperature for 19 hr, the reaction mixture was filtrated and
purified by silica gel chromatography (NH-silica gel, 20% EtOAc in hexane to EtOAc only, and silica
gel, 2% to 7% 2 M NH3/MeOH in CHC13) to give the desired product. The product was determined
byESI-MSorAPCl-MS.
Wherein the amines are selected from
N2~( a"5-4-amino-cyclohexyl)-AVv -dimethyl-quinoline-2,4-diamine obtained in step B of example 5,
N2-( c^^-aminomethyl-cyclohexy^-A^^-dimethyl-quinoline^^-diamine obtained in step B of
example 7, N -( c/^^-amino-cyclohexylJ-A^^v-dimethyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine
obtained in step B of example 13, N2-( c/s-4-aminomethyl-cyclohexyI)-A^,A^-dimethyl-5,6,7,8-
tetrahydro-quinazoline-2,4-diamine obtained in intermediate of step B of example 15, iV -( cis-4-
amino-cyclohexyl)-iV4;r/V4-dimethyl-pyrimidine-2,4-diamine obtained in step B of example 18, or
N2-( ci5-4-aminomethyl-cyclohexyl)-A^^\r-dimethyI-pyrimidine-2,4-diamine obtained in step B of
example 19.
Example 1659-2496
To a solution of amines (30 jimol) as shown below in DMSO (300 JJL) were added isocyanate
or isothiocyanate (60 ^mol) in DMSO (200 |_iL) at ambient temperature. The mixture was stirred at
the same temperature for 22 hr. To the reaction mixture were added 2 M MeNH2 in THF (30 pL, 60
p.mol) or D-gulcamine (60 j^mol) in DMSO (200 |_tL) at ambient temperature. After stirring at the

372
same temperature for 20 hr, the reaction mixture was filtrated through a SCX, concentrated by a
stream of dry N2, and purified by silica gel chromatography (silica gel, 2% to 10% 2 M NH3/MeOH in
CHCI3) and silica gel chromatography (NH-silica, 33% to 50% EtOAc in hexane) to give the desired
product. The product was determined by ESI-MS or APCI-MS.
Wherein the amines are selected from
N2-( c/5-4-amino-cyclohexyl)-AT;>Ar-dimethyl-quinoline-2,4-diamine obtained in step B of example 5,
N2-( cw-4-aminomethyl-cyclohexyl)-A^4^V4-dimethyl-quinoline-2,4-diamine obtained in step B of
example 7, N2-( ci5-4-amino-cyC1-5hexyl)-V,7V4-dimethyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine
obtained in step B of example 13, N2-( c/s-4-aminomethyl tetrahydro-quinazoline-2,4-diamine obtained in intermediate of step B of example 15, N2-( cis-A-
amino-cyclohexyl)-A/4,^-dimethyl-pyrimidine-2,4-diamine obtained in step B of example 18, or
N2-( c/5-4-aminomethyl-cyclohexyI)-A/4^V4-dimethyl-pyrimidine-2,4-diamine obtained in step B of
example 19.

373

Ex. No. compound name MS class
20 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-3-
methoxybenzamide 419 (M + H) 2
21 3-bromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexy])benzamide 467 (M + H) 1
22 4-bromo-N-(cis-4- {[4-(dimethylamino)quinolin-2-
y l]amino) cyclohexyl)benzamide 467 (M + H) 2
23 N-tcis-4-{[4-(dimethyIamino)quinolin-2-yI]amino}cyclohexyl)-
2,1,3-benzoxadiazoIe-5-carboxamide 431 (M + H) 1
24 3-chloro-N-(cis-4-{[4-(dimethyIamino)quinolin-2-
yllamino}cyclohexyl)benzamide 423 (M + H) 1
25 4-chloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)benzamide 423 (M + H) 1
26 (2E)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
ynamino}cvclohexyl)-3-phenylacrylamide 415 (M + H) -i
27 4-chloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyC1-5hexyl)-3-nitrobenzamide 468 (M + H) 1
28 2-(4-chIorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl"|amino}cyclohexyl)acetamide 437 (M + H)
29 3-cyano-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino) cyclohexyl)benzamide 414 (M + H) 2
30 3,5-dichloro-N-(cis-4-{[4-tdimethylamino)quinolin-2-
ynamino}cyclohexyl)benzamide 457 (M + H) 2
31 3,4-dichloro-N-(cis-4-{[4-(dimethyIamino)quinolin-2-
yl]amino}cyclohexyl)benzamide 457 (M + H) 1
32 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
2,2-diphenylacetamide 479 (M + H) 2
33 N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-
3,4-difluorobenzamide 425 (M + H) 1
34 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-
3,5-difluorobenzamide 425 (M + H) 2
35 2-(2,5-dimethoxyphenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-
2-yllamino) cyclohexy I)acetamide 463 (M + H) 3
36 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yI]amino}cyclohexyl)-2-
(ethylthio)nicotinamide 450 (M + H) 3
37 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-
fluorobenzamide 407 (M + H) 1
38 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-
fluoro-5-(trifluoromethyl)benzamide 475 (M + H) 2
39 2,4-dichloro-N-(qis-4-{[4-(dimethylamino)quinolin-2-
yilamino}cyclohexyl)-5-fluorobenzamide 475 (M + H) 3
40 N-(cis-4- {[4-(dimethylamino)quinoiin-2-
yllamino} cyclohexy I )hexanamide 383 (M + H) 3
41 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-4-
iodobenzamide 515 (M + H) 3
42 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(methylthio)nicotinamide 436 (M + H)
43 N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyI)-4-
methyl-3-nitrobenzarnide 448 (M + H) 2

374

Ex. No. compound name MS class
44 N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-3-
nitrobenzamide 434 (M + H) 1
45 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
phenylacetamide 403 (M + H) 3
46 (2R)-N-(cis-4- {[4-(dimethy !amino)quinolin-2-
yl]amino}cyclohexyl)-2-phenylcyclopropanecarboxamide 429 (M + H) -i
47 N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-
1,3-benzodioxole-5-carboxamide 433 (M + H) 3
48 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyC1-5hexyl)-2-
phenoxybutanamide 447 (M + H) 1
49 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-2-
phenoxypropanamide 433 (M + H) 1
50 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-
methylbenzamide 403 (M + H) 1
51 N-(cis-4-{[4-(dimethy]amino)quinolin-2-yl]amino}cyclohexyl)-4-
methylbenzamide 403 (M + H) -i
52 N-(cis-4-{[4-(dimethylamino)quinolin-2-
yI]amino}cyclohexyI)thiophene-2-carboxamide 395 (M + H)
53 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-
(2-thieny])acetamide 409 (M + H) -1
54 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-3-
(trifluoromethoxy)benzamide 473 (M + H) 2
55 benzyl (cis-4-{[4-(dimethyIamino)quinoIin-2-
yllamino}cyclohexyl)carbamate 419 (M + H)
56 4-nitrobenzyl (cis-4-{[4-(dimethylamino)quinolin-2-
yllamino)cyclohexyl)carbamate 464 (M + H) 3
57 4-bromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyI)-3-methylbenzamide 481 (M + H) 1
58 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-
iodobenzamide 515 (M + H) 2
59 3-chloro-N-(cis-4-{[4-(dimethyIamino)quinolin-2-
yllamino)cvclohexyl)-2-fluorobenzamide 441 (M + H) 3
60 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-
2,3-dtfluoro-4-methylbenzamide 439 (M + H) ->
61 2-chIoro-N-(cis-4- {[4-(dimethyIamino)quinolin-2-
yllamino}cyclohexyl)-4-fIuorobenzamide 441 (M + H) -i
62 3-chloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyC1-5hexyl)-2,4-difluorobenzamide 459 (M + H) 2
63 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(phenylthio)acetamide 435 (M + H) 3
64 N-(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}cyclohexyl)-2-
fluoro-3-(trifluoromethyI)benzamide 475 (M + H) 3
65 N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyI)-2-
fluoro-5-(trifluoromethyI)benzamide 475 (M + H)
66 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
phenyibutanamide 431 (M + H) 3
67 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(3-methoxyphenyl)acetamide 433 (M + H) 3

375

Ex. No. compound name MS class
68 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(4-fluorophenyl)acetamide 421 (M + H) 3
69 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(4-methoxyphenyl)acetamide 433 (M + H) 3"
70 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-5-
methyI-2-(trifluoromethyl)-3-furamide 461 71 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
2,5-dimethyl-3-furamide 407 (M + H) 1
72 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
ethoxybenzamide 433 (M + H) 3
73 3-chloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyI)-4-fluorobenzamide 441 (M + H) 1
74 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-
fluoro-4-m ethy 1 benzam ide 421 (M + H) 2
75 2-cyclopentyl-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)acetamide 395 (M + H)
76 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
3,5-dimethoxybenzamide 449 (M + H) 1
77 4-cyano-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)benzamide 414 (M + H)
78 N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexyl)-
3,5-bis(trifluoromethyI)benzamide 525 (M + H) 2
79 (2E)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)-3-(4-nitrophenvl)acrylamide 460 (M + H) -*>
80 2-(2-bromophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
y!lamino}cyclohexvl)acetamide 481 (M + H) 3
81 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-4-
fluoro-3-methyIbenzamide 421 (M + H) 1
82 2-[(difluoromethyl)thio]-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino} cyclohexyl)benzaraide 471 (M + H) 3
83 2,5-dichloro-N-(cis-4-{[4-(dimethylamino)quinoIin-2-
vllamino}cyclohexyl)thiophene-3-carboxamide 463 (M + H) 2
84 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-
(propylthio)nicotinamide 464 (M + H) 3
85 l-benzyl-3-tert-butyl-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)-lH-pvrazole-5-carboxamide 525 (M + H) 3
86 3-tert-butyl-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino) cyclohexy I)-1 -methy 1-1 H-pyrazoIe-5-carboxamide 449 (M + H) 3
87 (2E)-N-(cis-4- {[4-(dimethylamino)quinolin-2-
yllamino}cyclohexy!)-2-methyI-3-phenylacrylamide 429 (M + H)
88 5-bromo-N-(cis-4- {[4-(dimethy lam ino)qui noli n-2-
vl]amino}cyclohexyl)nicotinamide 468 (M + H) 3
89 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-
{1 -naphthy l)acetamide 453 (M + H) J
90 1 -tert-butyl-N-(cis-4- {[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexy!)-5-methyl-lH-pyrazole-3-carboxamide 449 (M + H)
91 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-l-
benzothiophene-3-carboxamide 445 (M + H) 3

376

Ex. No. compound name MS class
92 2-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cvclohexyl)aminol-2-oxo-l-phenvlethyI acetate 461 (M + H)
93 N-(cis-4-{[4-(dimethyiamino)quinolin-2-
yl]amino} cyclohexyl)benzamide 389 (M + H) T
94 N-(cis-4-{[4-(dimethy]amino)quinolin-2-yI]amino}cyclohexyl)-l-
benzothiophene-2-carboxamide 445 (M + H)
95 2-(benzyIoxy)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)acetamide 433 (M + H) 3
96 2-(4-chlorophenoxy)-N-(cis-4-{[4-{dimethylamino)quinolin-2-
yl]amino}cyclohexyl)acetamide 453 (M + H) 1
97 N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)cyclohexanecarboxamide 395 (M + H) 3
98 3-(2-chIorophenyI)-N-(cis-4- {[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)-5-methylisoxazole-4-carboxamide 504 (M + H) 1
99 l-(4-chlorophenyl)-N-(cis-4-{[4-{dimethylamino)quinolin-2-
yl]amino}cyclohexyl)cyclopentanecarboxamide 491 (M + H) 2
100 3-(2-chloro-6-fluorophenyl)-N-(cis-4-{[4-
(dimethyIamino)quinolin-2-yl]amino}cyC1-5hexyl)-5-
methylisoxazole-4-carboxamide 522 (M + H) 1
101 3-chioro-N-(cis-4-{[4-(dimethylamino)quinolin-
2-yl]amino}cyclohexyl)-4-(isopropylsulfonyl)thiophene-
2-carboxamide 535 (M + H) 3
102 2-chloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyC1-5hexyl)-4-nitrobenzamide 468 (M + H) 3
103 N-(cis-4-{ [4-(dimethylamino)quinol in-2-yl]amino} cyclohexyl)-
l,3-dimethyl-lH-pyrazole-5-carboxamide 407 (M + H) 3
104 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
3,4-dimethoxybenzamide 449 (M + H)
105 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-
fl uorobenzam ide 407 (M + H) 2
106 N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexyl)-4-
fluoro-3-(trifluoromethyl)benzamide 475 (M + H) 1
107 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-5-
methyI-2-phenyI-2H-l,2,3-triazole-4-carboxamide 470 (M + H) 2
108 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(4-methoxyphenoxy)-5-nitrobenzamide 556 (M + H) 1
109 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-l-
naphthamide 439 (M + H) ->
110 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
naphthamide 439 (M + H) 3
111 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-5-
nitro-2-furamide 424 (M + H) 1
112 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
phenoxyacetamide 419 (M + H) 1
113 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-
(2-nitrophenoxy)acetamide 464 (M + H)
114 N-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)quinoxaline-2-carboxamide 441 (M + H) 2

377

Ex. No. compound name MS class
115 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
3,4,5-trimethoxybenzamide 479 (M + H) ">
116 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-
{trifluoromethyl)benzamide 457 (M + H) ■->
117 N-(cis-4-{[4-(dimethylamino)quinolin-2-yi]amino}cyclohexyl)-4-
(trifluoromethyl)benzamide 457 (M + H)
118 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(trtfluoromethoxy)benzamide 473 (M + H) -i
119 4,5-dimethoxy-2-nitrobenzyl (cis-4-{[4-(dimethylamino)quinolin-
2-yllamino}cyclohexyl)carbamate 524 (M + H) ■■*
120 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-
phenoxybutanamide 447 (M + H) 3
121 2-bromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yIlamino}cvclohexyl)-5-methoxybenzamide 497 (M + H)
122 N-(cis-4-{[4-(dimethyIamino)quinoIin-2-yl]amino}cyclohexyl)-2-
(pentafluorophenoxy)acetamide 509 (M + H) 3
123 2-(3,4-dimethoxyphenyl)-N-(cis-4-{[4-(dimethyIamino)quinolin-
2-yllamino}cyclohexyl)acetamide 463 (M + H)
124 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-
2,3,4-trifIuorobenzamide 443 (M + H) 3
125 N-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)cyclopentanecarboxamide 381 (M + H)
126 N-(cis-4- {[4-(dimethyIamino)quinolin-2-yl]amino} cyclohexy 1)-
2,4-difluorobenzamide 425 (M + H) ">
127 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cydohexyl)-3-
phenylpropanamide 417 (M + H) 3
128 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
2,3,4,5 -tetrafluorobenzam ide 461 (M + H) 3
129 N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexyl)-2-
ethoxy-1 -naphthamide 483 (M + H) 3
130 N-(cis-4-{[4-(dimethyiamino)quinolin-2-yl]amino}cyclohexyl)-
2,3-4,5,6-pentafluorobenzamide 479 (M + H)
131 N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexy 1 )-4-
[(tri fluoromethy l)th io]benzam ide 489 (M + H) 3
132 3,4.5-trichloro-N-(cis-4-{[4-(dimethylamino)quinoIin-2-
vllamino}cyclohexyl)thiophene-2-carboxamide 497 (M + H) 3
133 2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)acetamide 453 (M + H) 1
134 3-(2,6-dichlorophenyI)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyC1-5hexyl)-5-methylisoxazole-4-carboxamide 538 (M + H) 1
135 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
phenoxynicotinamide 4.82 (M + H) 1
136 N-(cis-4-{[4-(dimethyIamino)quinoIin-2-yl]amino}cyclohexyl)-2-
(phenylthio)nicotinamide 498 (M + H)
137 N-(cis-4-{[4-(dimethylamino)quinolin-2~yI]amino}cyclohexyl)-2-
(4-methylphenoxy)nicotinamide 496 (M + H) 1
138 N-(cis-4-{[4-(dimethy!amino)quinolin-2-yl]amino}cyclohexyI)-4-
r(dipropylamino)sulfonyl]benzamide 552 (M + H) 3

378

Ex. No. compound name MS class
139 2-(4-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)quinoIin-2-
yIlamino}cyclohexyl)-2-methylpropanamide 481 (M + H)
140 5-(4-chlorophenyl)-N-(cis-4-{[4-(dimethyIamino)quinolin-2-
y!lamino)cyclohexyl)-2-(trifluoromethyI)-3-furamide 557 (M + H) -1
141 2-(2,3-dihydro-l-benzofuran-5-y])-N-(cis-4-{[4-
(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
1,3-thiazole-4-carboxamide 514 (M + H) ->
142 3-tert-butyl-l-(2,4-dichlorobenzyl)-N-(cis-4-{[4-
(dimethyIamino)quinolin-2-yl]amino}cyC1-5hexyi)-
1 H-pyrazo I e- 5 -carboxam i de 593 (M + H)
143 6-chloro-N-(cis-4- {[4-(dimethy lamino)quinolin-2-
yI]amino}cyC1-5hexyl)-2H-chromene-3-carboxamide 477 (M + H) ->
144 3-chloro-N-(cis-4- {[4-(dimethylamino)quinolin-2-
ynamino}cyclohexyI)-4-(trifluoromethoxy)benzamide 507 (M + H) J
145 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
[(4-methyl-2-oxo-2H-chromen-8-yI)oxy]acetamide 501 (M + H) 3
146 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(2-thienyl)-l,3-thiazole-4-carboxamide 478 (M + H) 1
147 N-[(cis-4-{[4-(dimethylamino)quinoIin-2-
yllamino)cyc]ohexyI)methyll-3-methoxybenzamide 433 (M + H)
148 3-bromo-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
ytlamino}cyctohexyl)methyl]benzamide 481 (M + H) ->
149 4-bromo-N-[(cis-4- {[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyl]benzamide 481 (M + H) 3
150 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyC1-5hexyl)methyl]-2,l,3-benzoxadiazole-
5-carboxam ide 445 (M + H) 3
151 3-chloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyl]benzamide 437 (M + H) 3
152 4-chIoro-N-[(cis-4- {[4-(dimethy Iamino)quinolin-2-
yl]amino}cyclohexyl)methy[lbenzamide 437 (M + H)
153 (2E)-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yIlamino>cyclohexyl)methy!l-3-phenylacrylamide 429 (M + H)
154 4-chIoro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yIlammo)cyC1-5hexyl)methyIl-3-nitrobenzamide 482 (M + H)
155 2-(4-chIorophenyl)-N-[(cis-4-{[4-(dimethylamino)quinoIin-2-
y!]amino}cyclohexyl)methyllacetamide 451 (M + H) 3
156 3-cyano-N-[(cis-4-{[4-(dimethyIamino)quinolin-2-
yllamino)cyclohexyl)methyllbenzamide 428 (M + H) 3
157 3,5-dichloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyllbenzamide 471 (M + H)
158 3,4-dichIoro-N-[(cis-4~{[4-(dimethylamino)quinolin-2-
yllamino)cyclohexyl)methy!lbenzamide 471 (M + H) ^>
159 N-[(cis-4-{[4-(dimethylamino)quinoIin-2-
yl|amino)cyclohexyl)methyIl-2,2-diphenylacetamide 493 (M + H) 2
160 N-[(cis-4-{[4-(dimethylamino)quinoIin-2-
yI]amino)cyclohexyI)methyl]-3,4-difluorobenzamide 439 (M + H)

379

Ex. No. compound name MS class
161 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methvl]-3,5-difluorobenzamide 439 (M + H)
162 2-(2,5-dimethoxyphenyl)-N-[(cis-4-{[4-(dimethylamino)quinolin-
2-yl]amino}cyclohexyl)methyr|acetamide 477 (M + H) 3
163 N-[(cis-4-{[4-(dimethyIamino)quinolin-2-
yl]amino}cyclohexyl)methyl]-2-(ethylthio)nicotinamide 464 (M + H) 3
164 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyl]-4-fluorobenzamide 421 (M + H) -i
165 N-[(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-
methyl]-3-fluoro-5-(trifluoromethyl)benzamide 489 (M + H)
166 2,4-dichloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyl]-5-fiuorobenzamide 489 (M + H) 3
167 N-[(cis-4-{[4-(dimethylamino)qirinolin-2-
yllamino}cyclohexyl)methyl]hexanamide 397 (M + H) -i
168 N-[(cis-4-{[4-(dimethylammo)quinolin-2-
yl]amino}cyclohexyl)methyll-4-iodobenzamide 529 (M + H) 3
169 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyl]~2-(methvltbio)nicotinamide 450 (M + H) 3
170 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyl]-4-methyl-3-nitroberizamide 462 (M + H) -i
171 N-[(cis-4- {[4-(dimethy lamino)quinolin-2-
yl]amino}cyclohexyl)methyIl-3-nitrobenzamide 448 (M + H) 3
172 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyll-2-phenylacetamide 417 (M + H)
173 (2R)-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyn-2-phenylcyclopropanecarboxamide 443 (M + H) 3
174 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyI)methyll-l,3-benzodioxole-5-carboxamide 447 (M + H) 3
175 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino)cyclohexyl)methyl]-2-phenoxybutanamide 461 (M + H) 3
176 N-[(cis-4-{[4-(dimethylamino)quinoIin-2-
yllamino}cyclohexyl)methyn-2-phenoxypropanamide 447 (M + H) 3
177 N-[(cis-4-{[4-(dimethyIamino)quinolin-2-
yllamino}cyC1-5hexyI)methyl]-3-methyIbenzamide 417 (M + H) 3
178 N-[(cis-4-{[4-(dimethyIamino)quinolin-2-
yllamino}cyclohexyl)methyll-4-methyIbenzamide 417 (M + H)
179 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyllthiophene-2-carboxamide 409 (M + H) t
180 N-[(cis-4-{[4-(dimethyIamino)quinolin-2-
yl]amino}cyclohexyI)methyll-2-(2-thienyl)acetamide 423 (M + H)
181 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyl]-3-(trifluoromethoxy)benzamide 487 (M + H) ■>
182 [4-(4-Dimethylamino-quinoIin-2-yIamino)-cyclohexylmethyl]-
carbamic acid benzyl ester 433 (M + H) 3
183 [4-(4-Dimethylamino-quinolin-2-ylamino)-cyclohexylmethyl]-
carbamic acid 4-nitro-benzvl ester 478 (M + H) 3
184 4-bromo-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllaraino}cyclohexyl)methyI]-3-methyIbenzamide 495 (M + H) 3

380

Ex. No. compound name MS class
185 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyC1-5hexvl)methyl]-3-iodobenzaniide 529 (M + H) -■>
186 3-chloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyll-2-fluorobenzamide 455 (M + H)
187 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyl]-2,3-difluoro-4-methylbenzamide 453 (M + H) 1
188 2-chIoro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyll-4-fluorobenzamide 455 (M + H) 1
189 3-chIoro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyC1-5hexyl)methyn-2,4-dif!uorobenzamide 473 (M + H) 3
190 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyl]-2-(phenylthio)acetamide 449 (M + H) 3
191 N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}cyclohexyl)-
methyIl~2-fluoro-3-(trifluoromethyI)benzamide 489 (M + H) 3
192 N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-
methyl]-2-fluoro-5-(trifluoromethyl)benzamide 489 (M + H)
193 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyl]-2-phenylbutanamide 445 (M + H) 3
194 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
ynamino}cyclohexyl)methyll-2-(3-methoxyphenyl)acetamide 447 (M + H) 3
195 N-[(cis-4- {[4-(dimethy lamino)quinolin-2-
yl]amino}cyclohexyl)methyll-2-(4-fluorophenyl)acetamide 435 (M + H)
196 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyll-2-(4-methoxyphenyI)acetamide 447 (M + H) 3
197 N-[(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexyl)-
methyll-5-methyl-2-(trifluoromethyl)-3-furamide 475 (M + H) 3
198 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yI]amino}cyclohexyl)methyll-2,5-dimethyl-3-furamide 421 (M + H)
199 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyl]-2-ethoxybenzamide 447 (M + H) 3
200 3-chloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyll-4-fluorobenzamide 455 (M + H) 3
201 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yI]amino}cyclohexyl)methyl]-3-fiuoro-4-methyIbenzamide 435 (M + H) 3
202 2-cyC1-5pentyl-N-[(cis-4-{[4-(dimethyIamino)quinoIin-2-
yl]amino}cyclohexyl)methyllacetamide 409 (M + H) 3
203 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyc!ohexyl)methyll-3,5-dimethoxybenzamide 463 (M + H) 3
204 4-cyano-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
ynamino}cyclohexyl)methyllbenzamide 428 (M + H)
205 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyc]ohexyl)methyl]-3,5-bis(trifluoromethyl)benzamide 539 (M + H) 3
206 (2E)-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyll-3-(4-nitrophenyl)acrylamide 474 (M + H) 2
207 2-(2-bromophenyl)-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyllacetamide 495 (M + H) 3
208 N-[(cis-4-{[4-(dimethylamino)quinoIin-2-
yl]amino}cyclohexyl)methyll-4-fluoro-3-methylbenzamide 435 (M + H) 3

381

Ex. No. compound name MS class
209 2-[(difluoromethyl)thio]-N-[(cis-4-{[4-{dimethylamino)quinolin-
2-yllamino}cyclohexyl)methyllbenzamide 485 (M + H) 3
210 2,5-dichloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyl]thiophene-3-carboxamide 477 (M + H) 3
211 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyl]-2-(propyIthio)nicotinamide 478 (M + H) 3
212 l-benzyl-3-tert-butyl-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyl]-lH-pyrazole-5-carboxamide 539 (M + H)
213 3-tert-buty l-N-[(cis-4- {[4-(dimethy lamino)quinolin-2-
yi]amino} cyclohexyl)methyl]-1 -methyl-1 H-pyrazole-
5-carboxamide 463 (M + H)
214 (2E)-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyI)methyl]-2-methyl-3-phenylacrylamide 443 (M + H) 3
215 5-bromo-N-[(cis-4-{[4-(dimethylaraino)quinolin-2-
yl]amino}cyclohexyl)methyllnicotinamide 482 (M + H)
216 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyll-2-(l-naphthyl)acetamide 467 (M + H) -y
217 l-tert-butyl-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyl]-5-methyl-lH-pyrazoIe-
3-carboxamide 463 (M + H)
218 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino)cyclohexyl)methyll-l-benzothiophene-3-carboxamide 459 (M + H) 3
219 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyI)methyllbiphenvl-4-carboxamide 479 (M + H) 3
220 2-bromo-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
y!]amino}cyclohexyl)methyl]benzamide 481 (M + H) 3
221 2,6-dichloro-N-[(cis-4-{[4-(dimethylamino)quinoIin-2-
yl]amino}cyclohexyl)methyllbenzamide 471 (M + H) 2
222 N-[(cis-4- {[4-(dimethy lamino)quinolin-2-
yI]amino}cyclohexyl)methyll-2-iodobenzamide 529 (M + H)
223 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yI]amino}cyclohexyl)methyll-2-methylbenzamide 417 (M + H) 3
224 2,3-dichIoro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
vnamino}cyclohexyl)methyl]benzamide 471 (M + H) ->
225 2-ch!oro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yIlamino)cyclohexyl)methyl]-5-fIuorobenzamide 455 (M + H) ->
226 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyll-9-oxo-9H-fluorene-4-carboxamide 505 (M + H) 3
227 N-[{cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyll-2,3,6-trifluorobenzamide 457 (M + H) 3
228 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
y!lamino}cyclohexyl)methyl]-2,3-difluorobenzamide 439 (M + H) 3
229 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyn-2,6-difluorobenzamide 439 (M + H) ->
230 N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
methylV2-fIuoro-6-(trifluoromethyl)benzamide 489 (M + H)
231 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino)cyclohexyl)methyl]-2,4,6-trimethylbenzamide 445 (M + H) 1

382

Ex. No. compound name MS class
232 2-chloro-N-[(cis-4- {[4-(dimethy lam ino)qui noli n-2-
yl]amino}cyclohexyl)methy!]-6-fluorobenzamide 455 (M + H) t
233 2,4,6-trichloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexy])methyl]benzamide 505 (M + H) 1
234 (2E)-3-(2-chlorophenyl)-N-[(cis-4-{[4-(dimethylamino)quinolin-
2-yl]amino}cyclohexyl)methyllacrylamide 463 (M + H) 2
235 6-chloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyl]-2-fluoro-3-methylbenzamide 469 (M + H) 3
236 2-chloro-N-[(cis-4- {[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyll-3,6-difluorobenzamide 473 (M + H)
237 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyc]ohexy!)methyl]-2,3-dimethylbenzamide 431 (M + H) 3
238 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
3-methoxybenzamide 370 (M + H) 2
239 3-bromo-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-
yllamino} cyclohexyl)benzamide 418 (M + H) 1
240 4-bromo~N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyi)benzamide 418 (M + H) 3
241 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2,1,3-benzoxadiazole-5-carboxamide 382 (M + H) 1
242 3-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)benzamide 374 (M + H) 1
243 4-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)benzamide 374 (M + H) 2
244 (2E)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino)cyc!ohexyl)-3-phenyIacrylamide 366 (M + H)
245 4-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)-3-nitrobenzamide 419 (M + H) 1
246 2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)acetamide 388 (M + H) 3
247 3-cyano-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyclohexyl)benzamide 365 (M + H) 3
248 3,5-dichloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
ynamino}cyclohexyl)benzamide 408 (M + H) 1
249 3,4-dichloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)benzamide 408 (M + H) 1
250 N-(cis-4-{[4-(dimethy!amino)pyrimidin-2-yl]amino}cyclohexyl)-
2,2-diphenylacetamide 430 (M + H) 2
251 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexyl)-
3,4-difluorobenzamide 376 (M + H) 1
252 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
3,5-difluorobenzamide 376 (M + H) 2
253 2-(2,5-dimethoxyphenyl)-N-(cis-4-{[4-
(dimethvlamino)pyrimidin-2-yllamino}cyclohexyI)acetamide 414 (M + H) 3
254 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(ethylthio)nicotinamide 401 (M + H) ->
255 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
4-fluorobenzamide 358 (M + H) 3

383

Ex. No. compound name MS class
256 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
3-fiuoro-5-(trifluoromethyl)benzamide 426 (M + H) 2
257 2,4-dichIoro-N-(cis-4-{[4-(dimethy!amino)pyrimidin-2-
y!]amino)cyclohexyl)-5-fluorobenzamide 426 (M + H) 3
258 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)hexanamide 334 (M + H)
259 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
4-iodobenzamide 466 (M + H) 3
260 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
2-(methylthio)nicotinamide 387 (M + H) i
261 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
4-methyl-3-nitrobenzamide 399 (M + H) 2
262 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
3-nitrobenzamide 385 (M + H) 1
263 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-phenylacetamide 354 (M + H)
264 (2R)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)-2-phenylcyclopropanecarboxamide 380 (M + H) 3
265 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
l,3-benzodioxo!e-5-carboxamide 384 (M + H) 3
266 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-phenoxybutanamide 398 (M + H) 2
267 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-phenoxypropanamide 384 (M + H) ->
268 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
3-methvlbenzamide 354 (M + H) 2
269 N-(cis-4- {[4-(dimethy lamino)pyrimidin-2-yl]amino} cyclohexy])-
4-methylbenzamide 354 (M + H) 3
270 N-(cis-4-{[4-(dimethylamino)pyrimtdin-2-
yI]amino}cyC1-5hexyl)thiophene-2-carboxamide 346 (M + H)
271 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(2-thienyl)acetamide 360 (M + H) 3
272 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-y IJamino} cyclohexyl)-
3-{trif!uoromethoxy)benzamide 424 (M + H) 1
273 [4-(4-DimethyIamino-pyrimidin-2-yIamino)-cyclohexyl]-carbamic
acid benzyl ester 370 (M + H) ■>
274 [4-(4-Dimethylamino-pyrimidin-2-ylamino)-cyclobexyl]-carbamic
acid 4-nitro-benzyl ester 415 (M + H) 3
275 4-brorao-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cvclohexyI)-3-methyIbenzamide 432 (M + H) 1
276 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
3-iodobenzamide 466 (M + H) 1
277 3-chloro-N-(cis-4- {[4-(dimethylamtno)pyrimidin-2-
yl]amino}cyclohexy!)-2-fluorobenzamide 392 (M + H) •>
278 N-(cis-4-{[4-(dimethylaraino)pyrimidin-2-yl]amino}cyclohexyl)-
2,3-difluoro-4-methylbenzamide 390 (M + H) ->
279 2-chloro-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyI)-4-fIuorobenzamide 392 (M + H) 3

184

Ex. No. compound name MS class
280 3-chloro-N-(cis-4- {[4-(dimethy lamino)pyrimidin-2-
yl]amino}cyclohexyl)-2,4-difluorobenzamide 410 (M + H) ->
281 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(phenylthio)acetamide 386 (M + H)
282 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-fluoro-3-(trifluoromethy!)benzamide 426 (M + H)
283 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-fluoro-5-(trifluoromethyl)benzamide 426 (M + H) 3
284 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
2 -pheny 1 butanam i de 382 (M + H) 3
285 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(3-methoxyphenyl)acetamide 384 (M + H) "i
286 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(4-fluorophenyl)acetamide 372 (M + H) 3
287 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(4-methoxyphenyl)acetamide 384 (M + H) 3
288 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yi]amino}cyclohexyl)-
5-methyl-2-(trifluoromethyl)-3-furamide 412 (M + H) ->
289 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2,5-dimethyl-3-furamide 358 (M + H) 2
290 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-ethoxvbenzamide 384 (M + H) 3
291 3-chloro-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-
yl]amino)cyclohexyl)-4-fluorobenzamide 392 (M + H) 1
292 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
3-fluoro-4-methy!benzamide 372 (M + H)
293 2-cyclopentyl-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)acetamide 346 (M + H) 3
294 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
3,5-dimethoxybenzamide 400 (M + H) 1
295 4-cyano-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cvclohexy!)benzamide 365 (M + H)
296 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
3,5-bis(trifIuoromethyl)benzamide 476 (M + H) 1
297 (2E)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyt)-3-(4-nitrophenyI)acrylamide 411 (M + H) 3
298 2-(2-bromophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)acetamide 432 (M + H) 3
299 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
4-fluoro-3-methylbenzamide 372 (M + H) 1
300 2-[(difluoromethyl)thio]-N-(cis-4-{[4-(dimethylamino)pyrimidin-
2-yl]amino}cyclohexyI)benzamide 422 (M + H) 3
301 2,5-dichloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyI)thiophene-3-carboxamide 414 (M + H) 2
302 N-(cis-4-{[4-{dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
2-(propylthio)nicotinamide 415 (M + H) ^
303 l-benzyl-3-tert-butyl-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino) cyclohexy!)-1 H-pyrazole-5-carboxamide 476 (M + H) 2

385

Ex. No. compound name MS class
304 3-tert-butyl-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyI)-l-methyl-lH-pyrazole-5-carboxamide 400 (M + H)
305 (2E)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)-2-methyl-3-phenylacrylamide 380 (M + H)
306 5-bromo-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyclohexyl)nicotinamide 419 (M + H) •>
307 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-( 1 -naphthy l)acetamide 404 (M + H) 2
308 l-tert-butyl-N-(cis-4-{[4-(dimethyiamino)pyrimidin-2-
yl]amino) cyclohexyl)-5-methyl-1 H-pyrazole-3-carboxamide 400 (M + H) 3
309 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
l-benzothiophene-3-carboxamide 396 (M + H) -i
310 2-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyc!ohexyl)amino]-2-oxo-l-phenylethyl acetate 412 (M + H) 3
311 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)benzamide 340 (M + H) 3
312 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-
1 -benzothiophene-2-carboxamide 396 (M + H) 3
313 2-(benzy loxy)-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)acetamide 384 (M + H) 3
314 2-(4-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)acetamide 404 (M + H) 1
315 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cydohexyl)cyclohexanecarboxamide 346 (M + H) 3
316 3-(2-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimtdin-2-
yl]amino}cyclohexyl)-5-methylisoxazole-4-carboxamide 455 (M + H) 3
317 l-(4-chIorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)cyclopentanecarboxamide 442 (M + H) 2
318 3-(2-chloro-6-fluorophenyl)-N-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
5-methylisoxazole-4-carboxamide 473 (M + H) 2
319 3-chloro-N-(cis-4-{[4-(dimethyIamino)pyrimidin-
2-yi]amino}cyclohexyl)-4-(isopropyIsulfonyl)thiophene-
2-carboxamide 486 (M + H) 3
320 2-chloro-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-
y!]amino}cyclohexyl)-4-nitrobenzamide 419 (M + H) 3
321 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
1,3-dimethyl-1 H-pyrazole-5-carboxamide 358 (M + H) 3
322 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexy 1)-
3,4-dimethoxybenzamide 400 (M + H) 3
323 N-(cis-4- {[4-(dimethy lamino)pyrimidin-2-yl]amino} cyclohexyl)-
3-fluorobenzamide 358 (M + H) 3
324 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-
4-fluoro-3-(trifluoromethyI)benzamide 426 (M + H) 1
325 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-
5-methyl-2-phenyl-2H-l,2,3-triazole-4-carboxamide 421 (M + H) 1
326 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexy 1)-
2 -(4-m ethoxy ph en oxy )-5 -n ttrobenzam ide 507 (M + H) 1

186

Ex. No. compound name MS class
327 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
1-naphthamide 390 (M + H) 3
328 N-(cis-4-{[4-(dimethy]amino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
2-naphth amide 390 (M + H) ->
329 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexy])-
5 -n itro-2-furam ide 375 (M + H) ->
330 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-phenoxyacetamide 370 (M + H) 2
331 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(2-nitrophenoxy)acetamide 415 (M + H) ->
332 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyC1-5hexyI)quinoxaline-2-carboxamide 392 (M + H) 1
333 N'(cis-4-{[4-(dtmethylamino)pyrimidin--2-yl]amino}cyclohexyI)-
3,4,5-trimethoxybenzamide 430 (M + H) 3
334 N-(cis-4~{[4-(dimethylamino)pyrimidin'2-yl]amino}cyclohexyl)-
3-(trifluoromethyl)benzamide 408 (M + H) 2
335 N-(cis-4-{[4-(dimethylamino)pyrimidin~2-yl]amino}cyclohexyl)-
4-(trifIuoromethyl)benzamide 408 (M + H)
336 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexyl)-
2-(trifluoromethoxy)benzamide 424 (M + H)
337 4,5-dimethoxy-2-nitrobenzyl (cis-4-{[4-
(dimethylamino)pynmidin-2-yl]amino}cyclohexyl)carbamate 475 (M + H)
338 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
4 -phenoxy butanam ide 398 (M + H) 3
339 2-bromo-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
y 11 am i no } eye lohexy 1 )-5 -meth oxyben zam ide 448 (M + H) ■^
340 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyI)-
2-(pentafluorophenoxy)acetamide 460 (M + H) 2
341 2-(3,4-dimethoxyphenyl)-N-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yllamino}cyclohexyl)acetamide 414 (M + H) 3
342 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2,3,4-trifluorobenzamide 394 (M + H) 3
343 N-(cis-4-{[4-(dimethy]amino)pyrimidin-2-
yl]amino}cyclohexyl)cyclopentanecarboxamide 332 (M + H) 3
344 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyclohexyl)-
2,4-diffuorobenzamide 376 (M + H) 3
345 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
3-phenyipropanamide 368 (M + H) 3
346 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyi)-
2,3,4,5 -tetrafluoroben zam i de 412 (M + H) 3
347 N-(cis-4-{[4-(dimethy]amino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
2-ethoxy-1 -naphthamide 434 (M + H) 3
348 N-(cis-4-{[4-(dimethyiamino)pyrimidin-2-yI]amino}cyclohexyI)-
2,3,4,5,6-pentafIuorobenzamide 430 (M + H) 3
349 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
4-[(trifluoromethyl)thio]benzamide 440 (M + H)
350 3,4,5-trichloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)thiophene-2-carboxamide 448 (M + H) 3

387

Ex. No. compound name MS class
351 2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexy!)acetamide 404 (M + H) 1
352 3-(2,6-dichIorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)-5-methylisoxazole-4-carboxamide 489 (M + H) 1
353 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
2-phenoxynicotinamide 433 (M + H) 2
354 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(phenylthio)nicotinamide 449 (M + H)
355 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(4-methylphenoxy)nicotinamide 447 (M + H) 1
356 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyC1-5hexyl)-
4-[(dipropylamino)sulfonyllbenzamide 503 (M + H) 1
357 2-(4-chIorophenoxy)-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)-2-methyIpropanamide 432 (M + H) 2
358 5-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)-2-(trifluoromethyl)-3-furamide 508 (M + H) 3
359 2-(2,3-dihydro-l-benzofuran-5-yl)-N-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-l,3-thiazole-
4-carboxamide 465 (M + H) 1
360 3-tert-butyl-1 -(2,4-dichlorobenzyI)-N-(cis-4-{ [4-
(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-lH-pyrazole-
5-carboxamide 544 (M + H) 2
361 6-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyI)-2H-chromene-3-carboxamide 428 (M + H) 2
362 3-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyI)-4-(trifluoromethoxy)benzamide 458 (M + H) 3
363 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexyl)-
2-[(4-methyl-2-oxo-2H-chromen-8-yl)oxy]acetamide 452 (M + H) 3
364 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(2-thieny!)-l,3-thiazole-4-carboxamide 429 (M + H) 1
365 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
y!lamino}cyclohexyl)methyl]-3-methoxybenzamide 384 (M + H)
366 3-bromo-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yilamino}cyclohexyl)methyl]benzamide 432 (M + H)
367 4-bromo-N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl]amino}cyclohexyl)methyllbenzamide 432 (M + H) 3
368 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyi)methyl]-2,l,3-t)enzoxadiazole-
5-carboxamide 396 (M + H) 3
369 3-chloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexy!)methyl]benzamide 388 (M + H) •>
370 4-chloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
y!]amino}cyclohexyOmethyllbenzamide 388 (M + H) 2
371 (2E)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino)cyclohexyI)methyI]-3-phenylacrylamide 380 (M + H) 2
372 4-chloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyn-3-nitrobenzamide 433 (M + H) 2

388

Ex. No. compound name MS class
373 2-(4-chlorophenyl)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyllacetamide 402 (M + H) 2
374 3-cyano-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyi)methyl]benzamide 379 (M + H) -*>
375 3,5-dichloro-N-[tcis-4-{[4-(dimethylamino)pyrimidin-2-
y!lamino}cyclohexyl)methyl]benzamide 422 (M + H) 2
376 3,4-dichloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methy]~|benzamide 422 (M + H) 2
377 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]-2,2-diphenylacetamide 444 (M + H) 1
378 N-[(cis-4-{[4-tdimethylamino)pyrimidin-2-
yllamino)cyclohexyl)methyl]-3,4-difluorobenzamide 390 (M + H) ->
379 N-[(cis-4-{[4-(dimethylamino)pyrimtdin-2-
ynamino}cyclohexyl)methyIl-3,5-difluorobenzamide 390 (M + H) 3
380 2-(2,5-dimethoxyphenyl)-N-[(cis-4-{[4-(dimethyIamino)-
pyrimidin-2-yllamino}cyclohexyl)methyllacetamide 428 (M + H)
381 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyc]ohexyl)methyll-2-(ethylthio)nicotinamide 415 (M + H) 3
382 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl~|-4-fluorobenzamide 372 (M + H) 3
383 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
methy 11 -3 -fluoro- 5 -(tri ft uoromethy 1 )ben zam i de 440 (M + H)
384 2,4-dichloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyI)methyl]-5-fluorobenzamide 440 (M + H) 2
385 N-[(cis-4- {[4-(dimethy lamino)pyrimidin-2-
yl]amino}cyclohexyl)methy]]hexanamide 348 (M + H)
386 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyll-4-iodobenzamide 480 (M + H)
387 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyIl-2-(methylthio)nicotinamide 401 (M + H) ->
388 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino)cyclohexyl)methyl]-4-methvl-3-nitrobenzamide 413 (M + H) "i
389 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yI]amino}cyclohexyl)methyI]-3-nitrobenzamide 399 (M + H) 3
390 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyc]ohexyl)methyn-2-phenyIacetamide 368 (M + H) 3
391 (2R)-N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyclohexyl)methyl]-2-phenyIcyclopropanecarboxamide 394 (M + H)
392 N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyclohexyl)methyl]-l,3-benzodioxole-5-carboxamide 398 (M + H) 3
393 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yIlamino}cyclohexyl)methyl]-2-phenoxybutanamide 412 (M + H) 2
394 N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]-2-phenoxypropanamide 398 (M + H) 3
395 N-[(cis-4-{[4-(dimethytamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]-3-methy]benzamide 368 (M + H) ->
396 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
ynamino}cyC1-5hexyl)methyl]-4-methylbenzamide 368 (M + H) 3

389

Ex. No. compound name MS class
397 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyI)methyllthiophene-2-carboxamide 360 (M + H)
398 N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyclohexyl)methyll-2-(2-thienyl)acetamide 374 (M + H) ->
399 N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyclohexyl)methyll-3-(trifluoromethoxy)benzamide 438 (M + H)
400 benzyl [(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyllcarbamate 384 (M + H) 3
401 4-nitrobenzyl [(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyllcarbamate 429 (M + H) J
402 4-bromo-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyIl-3-methylbenzamide 446 (M + H) 3
403 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyll-3-iodobenzamide 480 (M + H)
404 3-chloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyll-2-fluorobenzamide 406 (M + H)
405 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyl]-2,3-difluoro-4-methylbenzamide 404 (M + H) 3
406 2-chloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyC1-5hexyl)methyl]-4-fluorobenzamide 406 (M + H) 3
407 3-chloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
vllamino}cyclohexyl)methyl]-2,4-difluorobenzamide 424 (M + H) 3
408 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methy!l-2-(phenylthio)acetamide 400 (M + H) 3
409 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
methyll-2-fluoro-3-(trifIuoromethyl)benzamide 440 (M + H) 3
410 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yi]amino}cyclohexyl)-
methyl]-2-fIuoro-5-(trifluoromethyl)benzamide 440 (M + H) 3
411 N-[(cis-4-{[4-(dimethyiamino)pyrimidin-2-
yl]amino}cyclohexyl)methyn-2-phenylbutanamide 396 (M + H) 1
412 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
vllamino}cyclohexyI)methyll-2-(3-methoxyphenyl)acetamide 398 (M + H) 2
413 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyl]-2-(4-fIuorophenyl)acetamide 386 (M + H) 3
414 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
vl]amino}cyclohexyl)methyl]-2-(4-methoxyphenyl)acetamide 398 (M + H) 2
415 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
methyll-5-methy!-2-(trifluoromethyl)-3-furamide 426 (M + H)
416 N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyl]-2,5-dimethyl-3-furamide 372 (M + H)
417 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yI]amino}cyclohexyl)methyll-2-ethoxybenzamide 398 (M + H)
418 3-chloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino)cyclohexyl)methyl]-4-fluorobenzamide 406 (M + H)
419 N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyll-3-fluoro-4-methy!benzamide 386 (M + H) 3
420 2-cyclopentyl-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllaminojcyclohexyl)methyl]acetamide 360 (M + H)

390

Ex. No. compound name MS class
421 N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyclohexyi)methyIl-3,5-dimethoxybenzamide 414 (M + H) -i
422 4-cyano-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyllbenzamide 379 (M + H) -■>
423 N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl]amino}cyclohexyI)methyl]-3,5-bis(trifluoromethyl)benzamide 490 (M + H) 2
424 (2E)-N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
vllamino}cyclohexy!)methyl]-3-{4-nitrophenyl)acrylamide 425 (M + H) 1
425 2-(2-bromophenyl)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino)cyclohexyl)methyl]acetamide 446 (M + H) 2
426 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyC1-5hexyl)methyll-4-fluoro-3-methylbenzamide 386 (M + H) ->
427 2-[{difluoromethyl)thio]-N-[(cis-4-{[4-(dimethylamino)-
pvrimidin-2-yl]amino}cyclohexyl)methyl]benzamide 436 (M + H) 3
428 2,5-dichloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyC1-5hexyl)methyl]thiophene-3-carboxamide 428 (M + H)
429 N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-
y!]araino}cyclohexyl)methyl]-2-(propylthio)nicotinamide 429 (M + H) 2
430 1 -benzyl-3-tert-buty!-N-[(cis-4- {[4-(dimethy lamino)pyrimidin-2-
yI"|amino}cyclohexyl)methyl]-lH-pyrazole-5-carboxamide 490 (M + H) 3
431 3-tert-butyl-N-[(cis-4-{[4-(dimethylamino)-pyrimidin-2-
yljamino} cyclohexyl)methyl]-1 -methyl-1 H-pyrazole-
5-carboxamide 414 (M + H) 3
432 (2E)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyI]-2-methyl-3-phenylacrylamide 394 (M + H) 3
433 5-bromo-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]nicotinamide 433 (M + H)
434 N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-
vl]amino} cyclohexvl)methyl]-2-( 1 -naphthyl)acetamide 418 (M + H) 1
435 l-tert-butyl-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyI]-5-methyl-lH-pyrazole-
3-carboxamide 414 (M + H) -i
436 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyI)methyI]-l-benzothiophene-3-carboxamide 410 (M + H) 3
437 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
vllamino}cyclohexyl)methyl]biphenyl-4-carboxamide 430 (M + H)
438 2-bromo-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
vllamino}cvclohexyl)methynbenzamide 432 (M + H) 3
439 2,6-dichloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
ynamino}cyclohexyl)methynbenzamide 422 (M + H)
440 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
ynamino}cyclohexyl)methyI]-2-iodobenzamide 480 (M + H)
441 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyI]-2-methylbenzamide 368 (M + H)
442 2,3-dichIoro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]benzamide 422 (M + H)
443 2-chloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyl]-5-fluorobenzamide 406 (M + H) 3

391

Ex. No. compound name MS class
444 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
vl]amino}cyclohexyl)methyll-9-oxo-9H-fluorene-4-carboxamide 456 (M + H) 2
445 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexy!)methyIl-2,3,6-trifluorobenzamide 408 (M + H)
446 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyC1-5hexyl)methyl]-2,3-difluorobenzamide 390 (M + H) ■I
447 N-[(cis-4-{[4-(dimethyiamino)pyrimidin-2-
yl]amino}cyclohexyi)methyll-2,6-difluorobenzamide 390 (M + H) 3
448 N-[(cis-4-{[4-tdimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
m ethyl 1 -2-fluoro-6-(trifl u oromethy l)ben zam id e 440 (M + H) ">
449 N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyn-2,4,6-trimethylbenzamide 396 (M + H) 2
450 2-chloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]-6-fluorobenzamide 406 (M + H)
451 2,4,6-trichloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyllbenzamide 456 (M + H) 2
452 (2E)-3-(2-chlorophenyl)-N-[{cis-4--{[4-(dimethylamino)pyrimidin-
2-yllamino}cyclohexyl)methvl]acrvlamide 414 (M + H) 2
453 6-chloro-N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-
yI]amino}cyclohexyI)methyll-2-fluoro-3-methylbenzamide 420 (M + H) 3
454 2-chloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]-3,6-difluorobenzamide 424 (M + H) 3
455 N-[(cis-4-{[4-(dimethylammo)pyrimidin-2-
yllamino}cyclohexyl)methyll-2,3-dimethylbenzamide 382 (M + H) 3
456 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyc!ohexyl)-3-methoxybenzamide 424 (M + H) 1
457 3-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)benzamide 472 (M + H) 1
458 4-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yilamino}cyclohexyl)benzamide 472 (M + H) 2
459 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y!lamino)cyctohexyl)-2,l,3-benzoxadiazole-5-carboxamide 436 (M + H) 1
460 3-chIoro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-ynamino)cyclohexyl)benzamide 428 (M + H) 1
461 4-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)benzamide 428 (M + H) 1
462 (2E)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-
2-y!]amino}cyclohexyI)-3-phenylacrylamide 420 (M + H) ■■>
463 4-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroqutnazolin-2-yllamino}cyclohexyl)-3-nitrobenzamide 473 (M + H) 1
464 2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)acetamide 442 (M + H) 1
465 3-cyano-N-(cis-4- {[4-( dimethy lam ino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino)cyclohexyl)benzamide 419 (M + H) 1
466 3,5-dichloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)benzamide 462 (M + H) 1
467 3,4-dichloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)benzamide 462 (M + H) 1

392

Ex. No. compound name MS class
468 N-(cis-4-{[4-(dimethylamino)-5,6,7,84etrahydroquinazolin-2-
yl]amino}cyclohexyl)-2,2-diphenvlacetamide 484 (M + H) 1
469 N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyI)-3,4-difluorobenzamide 430 (M + H) 1
470 N-(cis-4-{[4-(dimethylamino)-5,6,7,8"tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-3,5-difluorobenzamide 430 (M + H) 1
471 2-(2,5-dimethoxyphenyl)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)acetamide 468 (M + H) 3
472 N-(cis-4-{[4-(dimethyIamino)-5,6,7,84etrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-(ethyithio)nicotinamide 455 (M + H)
473 N-(cis-4-{[4-(dimethylamino)-5,6,7,8'tetrahydroquinazolin-2-
yllamino}cyclohexyI)-4-fIuorobenzamide 412 (M + H) 1
474 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl>3-fluoro-5-ftrifluoromethyl)benzamide 480 (M + H) 1
475 2,4-dichloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)-5-fluorobenzamide 480 (M + H) 3
476 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexvl)hexanamide 388 (M + H) 2
477 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
vllamino}cyC1-5hexyl)-4-iodobenzamide 520 (M + H) 3
478 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino)cyclohexyI)-2-(methylthio)nicotinamide 441 (M + H) 3
479 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-4-methyl-3-nitrobenzamide 453 (M + H) 1
480 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoHn-2-
yl]amino}cyclohexyI)-3-nitrobenzamide 439 (M + H) 1
481 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexy])-2-phenylacetamide 408 (M + H) 3
482 (2R)-N-(cis-4-{[4-(dimethylamino)-5,6,7J8-tetrahydroquinazolin-
2-yilamino)cyclohexyl)-2-phenylcyclopropanecarboxamide 434 (M + H) 2
483 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyI)-l,3-benzodioxole-5-carboxamide 438 (M + H) 3
484 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)-2-phenoxybutananiide 452 (M + H) 1
485 N-(cis-4-{[4-{dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllaminolcyclohexyl)-2-phenoxypropanamide 438 (M + H) 1
486 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyI)-3-methylbenzamide 408 (M + H) 1
487 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-4-methylbenzamide 408 (M + H) 2
488 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)thiophene-2-carboxamide 400 (M + H)
489 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino)evC1-5hexyt)-2-(2-thienvl)acetamide 414 (M + H) 3
490 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyI)-3-(trifluoromethoxy)benzamide 478 (M + H) 2
491 [4-(4-Dimethy]amino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-
cyclohexyl]-carbamic acid benzyl ester 424 (M + H)

393

Ex. No. compound name MS class
492 [4-(4-Dimethylamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-
cyclohexyl]-carbamic acid 4-nitro-benzyl ester 469 (M + H)
493 4-bromo-N-(cis-4-{[4-(dimethylamirio)-5,6,7,8-
tetrahvdroquinazolin-2-yI]amino}cyC1-5hexyl)-3-methylbenzamide 486 (M + H) 2
494 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y!lamino)cyclohexyl)-3-iodobenzamide 520 (M + H) 1
495 3-chIoro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-y!]amino}cyclohexyl)-2-fluorobenzamide 446 (M + H) 3
496 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)-2,3-difluoro-4-methylbenzamide 444 (M + H)
497 2-chloro-N-(cis-4- {[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazoIin-2-yi]amino}cyclohexyI)-4-fluorobenzamide 446 (M + H) 2
498 3-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yllamino}cyclohexyl)-2,4-difluorobenzamide 464 (M + H) 3
499 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-2-(phenylthio)acetamide 440 (M + H) -t
500 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-fluoro-3-(trifluoromethyl)benzamide 480 (M + H)
501 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-2-fluoro-5-(trifluoromethyl)benzamide 480 (M + H) J
502 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y!]amino}cyclohexyl)-2-phenylbutanamide 436 (M + H) 3
503 N-(cis-4-{[4-(dimethylamino)-5;6,7,8-tetrahydroquinazolin-2-
yl]amino}cydohexyl)-2-(3-methoxyphenyl)acetamide 438 (M + H) 2
504 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-(4-fIuorophenyl)acetamide 426 (M + H) 1
505 N-(cis-4-{[4-(dimethylamino)-5T6,7,8-tetrahydroquinazolin-2-
vllamino}cyclohexyl)-2-(4-methoxyphenyl)acetamide 438 (M + H) 2
506 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino)cyclohexyl)-5-methyI-2-(trifluoromethyI)-3-furamide 466 (M + H) 2
507 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-2,5-dimethyl-3-furamide 412 (M + H) 1
508 N-(cis-4-{[4-(dimethyiamino)-5T6T7;,8-tetrahydroquinazolin-2-
y!lamino)cyclohexyl)-2-ethoxybenzamide 438 (M + H) 3
509 3-chIoro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)-4-fluorobenzamide 446 (M + H) 1
510 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-3-fiuoro-4-methylbenzamide 426 (M + H) 2
511 2-cyclopentyl-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)acetamide 400 (M + H) ->
512 N-(cis-4-{[4-(dimethylamino)-5T6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)-3,5-dtmethoxybenzamide 454 (M + H) 1
513 4-cyano-N-tcis-4-{[4-(dimethy!amino)-5,6,7,8-
tetrahydroquinazolin-2-yi]amino}cyC1-5hexyl)benzamide 419 (M + H) 3
514 N-(cis-4-{[4-(dimethy]amino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-3,5-bisftrifluoromethyl)benzamide 530 (M + H) 1
515 (2E)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-
2-yIlamino}cyclohexyl)-3-(4-nitropheny!)acrylamide 465 (M + H)

394

Ex. No. compound name MS class
516 2-(2-bromophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyck>hexyi)acetamide 486 (M + H) 3
517 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyl)-4-fluoro-3-methylbenzamide 426 (M + H) 1
518 2-[(difluoromethyl)thio]-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)benzamide 476 (M + H) ->
519 2,5-dichloro-N-(cis-4-{[4-{dimethylamino)-5,6J7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiophene-
3-carboxamide 468 (M + H) 1
520 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yllamino}cyC1-5hexyI)-2-(propylthio)nicotinamide 469 (M + H) 2
521 l-benzyl-3-tert-butyl-N-(cis-4-{[4-tdimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)-lH-pyrazole-5-
carboxamide 530 (M + H) 2
522 3-tert-butyl-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)-l-
methyl-lH-pyrazoIe-5-carboxamide 454 (M + H) 3
523 (2E)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yl]amino}cyclohexyl)-2-methyl-3-phenylacrylamide 434 (M + H)
524 5-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)nicotinamide 473 (M + H) 1
525 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-(l-naphthyl)acetamide 458 (M + H)
526 l-tert-butyl-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)-5-
methyl-lH-pyrazole-3-carboxamide 454 (M + H)
527 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino)cyC1-5hexyl)-l-benzothiophene-3-carboxamide 450 (M + H) 1
528 2-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllaraino}cyclohexyl)amino]-2-oxo-1 -phenylethyl acetate 466 (M + H) 1
529 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yilamino) cyclohexyl)benzamide 394 (M + H) 2
530 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino} cyclohexyl)-1 -benzothiophene-2-carboxamide 450 (M + H) ^
531 2-(benzyIoxy)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)acetamide 438 (M + H) 2
532 2-(4-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)acetamide 458 (M + H) 2
533 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)cyclohexanecarboxamide 400 (M + H)
534 3-(2-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)-5-methylisoxazole-
4-carboxamide 509 (M + H) 2
535 l-(4-chlorophenyI)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)-
cyclopentanecarboxamide 496 (M + H) 2

395

Ex. No. compound name MS class
536 3-(2-chloro-6-fluorophenyl)-N-(cis-4-{[4-(dimethyIamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)-5-
methylisoxazole-4-carboxamide 527 (M + H) 1
537 3-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)-4-
(isopropylsulfonyl)thiophene-2-carboxamide 540 (M + H) 3
538 2-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)-4-nitrobenzamide 473 (M + H) 3
539 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y!]amino}cyclohexyl)-l,3-dimethyl-lH-pyrazole-5-carboxamide 412 (M + H) 2
540 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
y]]amino}cyC1-5hexyI)-3,4-dimethoxybenzamide 454 (M + H) 3
541 N-tcis^-J^^dimethylamino^S^JjS-tetrahydroquinazolin^-
yl]amino}cyclohexyi)-3-fluorobenzamide 412 (M + H) 1
542 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyC1-5hexy!)-4-fluoro-3-(trifluoromethyl)benzamide 480 (M + H) 1
543 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-5-methyl-2-phenyl-2H-l,2,3-triazole-4-
carboxamide 475 (M + H) 2
544 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-2-(4-methoxyphenoxv)-5-nitrobenzamide 561 (M + H) 1
545 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexvl)-l-naphthamide 444 (M + H)
546 N-(cis-4- {[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexvl)-2-naphthamide 444 (M + H) 3
547 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-5--nitro-2-fiiramide 429 (M + H) 1
548 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-2-phenoxyacetamide 424 (M + H) 1
549 N-(cis-4-{[4~(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)-2-f2-nitrophenoxy)acetamide 469 (M + H) 3
550 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yI]amino}cyclohexyl)quinoxaIine-2-carboxamide 446 (M + H) 1
551 N-(cis-4-{[4-(dimethyIamino)-5,6,7J8-tetrahydroquinazolin-2-
yI]amino}cyclohexyi)-3,4,5-trimethoxybenzamide 484 (M + H) 3
552 N-(cis-4-{[4-(dimethylamino)-5,6,7;,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyI)-3-(trifIuoromethyl)benzamide 462 (M + H) 1
553 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexyl)-4-(trifluoromethyl)benzamide 462 (M + H) 3
554 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-(trifluoromethoxy)benzamide 478 (M + H) 3
555 4,5-dimethoxy-2-nitrobenzyl (cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-ynamino}cyclohexyI)carbamate 529 (M + H) 3
556 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-4-phenoxvbutanamide 452 (M + H)
557 2-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)-5-methoxybenzamide 502 (M + H) 3

396

Ex. No. compound name MS class
558 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyl)-2-(pentafluorophenoxy)acetamide 514(M + H)
559 2-(3,4-dimethoxyphenyl)-N-(cis-4- {[4-(dimethylamino)-5,6,7,8-
tetrahyd roq u i nazo lin-2-yl]amino}cyclohexy 1 )acetam i d e 468 (M + H)
560 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2.3,4-trifIuorobenzamide 448 (M + H) i
561 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yi]amino}cyclohexyi)cyclopentanecarboxamide 386 (M + H)
562 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)-2,4-difluorobenzamide 430 (M + H)
563 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyl)-3-phenylpropanamide 422 (M + H) 3
564 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)-2,3,4,5-tetrafluorobenzamide 466 (M + H) 3
565 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)-2-ethoxy-l-naphthamide 488 (M + H)
566 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)-2,3,4,5,6-pentafluorobenzamide 484 (M + H) 3
567 N-(cis-4-{[4-(dimethylamino)-556,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexvl)-4-[(trifIuoromethyl)thiolbenzamide 494 (M + H) -i
568 3,4,5-trichloro-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydro-
quinazolin-2-yllamino}cyclohexyl)thiophene-2-carboxamide 502 (M + H) 3
569 2-(3-chlorophenoxy)-N-(cis-4-{ [4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino)cyclohexyl)acetamide 458 (M + H) 1
570 3-(2,6-dich]orophenyl)-N-(cis-4-{[4-(dimethylamino)-556,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)-5-methylisoxazole-
4-carboxamide 543 (M + H) 1
571 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)-2-phenoxynicotinamide 487 (M + H) 2
572 N-(cis-4-{[4-(dimethy!amino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)-2-(phenyIthio)nicotinamide 503 (M + H) 3
573 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)-2-(4-methylphenoxy)nicotinamide 501 (M + H) 1
574 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyC1-5hexyl)-4-[(dipropyIamino)suIfonyl]benzamide 557 (M + H) 3
575 2-(4-chIorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyc!ohexyl)-2-
methylpropanamide 486 (M + H) 3
576 5-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)-2-(trifluoromethyl)-
3-furamide 562 (M + H)
577 3-tert-butyI-l-(2,4-dichIorobenzyl)-N-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazoIin-2-yl]amino}cyclohexyl)-lH-
pyrazole-5-carboxamide 598 (M + H) ->
578 6-chloro-N-(cis-4-{[4-{dimethylamino)-5,6,7,8-
tetrahydroquinazo!in-2-yI]amino}cyclohexyl)-2H-chromene-3-
carboxamide 482 (M + H) 3

397

Ex. No. compound name MS class
579 3-chIoro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazoIin-2-yl]amino}cyclohexyl)-4-(trifluoromethoxy)-
benzamide 512 (M + H)
580 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyI)-2-[(4-methyl-2-oxo-2H-chromen-8-
y!)oxv]acetamide 506 (M + H) 1
581 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexy])-2-(2-thienyl)-K3-thiazole-4-carboxamide 483 (M + H) 2
582 N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyC1-5hexyI)methyI]-3-methoxybenzamide 438 (M + H) 3
583 3-bromo-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)methyI]benzamide 486 (M + H) 2
584 4-bromo-N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yIlamino}cyclohexyl)methyllbenzamide 486 (M + H)
585 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]-2,l,3-benzoxadiazole-
5-carboxamide 450 (M + H) 3
586 3-chloro-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]benzamide 442 (M + H)
587 4-chloro-N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]benzamide 442 (M + H) 3
588 (2E)-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8'tetrahydroquinazolin-
2-yllamino}cyC1-5hexyl)methyl]-3-phenyIacrylamide 434 (M + H) 3
589 4-chloro-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]-3-
nitrobenzamide 487 (M + H)
590 2-(4-chlorophenyl)-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-vIlamino}cyclohexyl)methyl]acetamide 456 (M + H)
591 3-cyano-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yIlamino}cyc]ohexyl)methyl]benzamide 433 (M + H)
592 3,5-dichloro-N-[(cis-4-{[4-(dimethyiamino>5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)methyl]benzamide 476 (M + H) 3
593 3,4-dichloro-N-[(cis-4-{[4-(dimethy]amino>5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyC1-5hexyl)methyIlbenzamide 476 (M + H) -i
594 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyI)methyll-2,2-diphenylacetamtde 498 (M + H) 3
595 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino)cvclohexyI)methyn-3,4-difluorobenzamide 444 (M + H) 3
596 N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]-3,5-difluorobenzamide 444 (M + H) *■*
597 2-(2,5-dimethoxyphenyI)-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yilamino}cyclohexyl)methyllacetamide 482 (M + H) ">
598 N-[(cis-4-{[4-(dimethyIamino)-5,6,7;8-tetrahydroquinazolin-2-
yllamino}cvc]ohexyl)methyl]-2-(ethy]thio)nicotinamide 469 (M + H) 1
599 N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methyl]-4-fluorobenzamide 426 (M + H)

398

Ex. No. compound name MS class
600 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]-3-fluoro-5-
(trifluoromethyl)benzamide 494 (M + H) "i
601 2,4-dichloro-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)methyl]-5-
fluorobenzamide 494 (M + H) ■■>
602 N-[(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methy]]hexanamide 402 (M + H) 3
603 N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methyIl-4-iodobenzamide 534 (M + H)
604 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
vl]amino}cyc]ohexvI)methyll-2-(methylthio)nicotinamide 455 (M + H) ^>
605 N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyI)methyl]-4-methyI-3-nitrobenzamide 467 (M + H)
606 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyC1-5hexyl)methyll-3-nitrobenzamide 453 (M + H)
607 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyll-2-phenylacetamide 422 (M + H)
608 (2R)-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yl]amino}cyclohexyl)methyl]-2-phenylcyclopropane-
carboxamide 448 (M + H) *>
609 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino} cyclohexyl)methyll-l ,3-benzodioxole-5-carboxamide 452 (M + H)
610 N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyl)methyll-2-phenoxybiitananiide 466 (M + H) 3
611 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyll-2-phenoxypropanamide 452 (M + H)
612 N-[tcis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyI)methyil-3-methylbenzamide 422 (M + H)
613 N-[tcis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyl)methyI]-4-methylbenzamide 422 (M + H)
614 N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyC1-5hexyI)methyllthiophene-2-carboxamide 414 (M + H) 3
615 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyI)methyll-2-(2-thienyl)acetamide 428 (M + H)
616 N-[(cis-4-{[4-(dimethyIamino)-556,7,8-tetrahydroquinazoIin-2-
yl]amino}cyc]ohexyI)methyl]-3-(trifluoromethoxy)benzamide 492 (M + H) ^>
617 benzyl [(cis-4-{[4-(dimethy!amino)-5,6,7,8-tetrahydroquinazolin-
2-yllamino}cyclohexyI)methyllcarbamate 438 (M + H) 3
618 4-nitrobenzyl [(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-ynamino}cyclohexyl)methy]lcarbamate 483 (M + H) 3
619 4-bromo-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]-3-
methylbenzamide 500 (M + H) -i
620 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)methyl]-3-iodobenzamide 534 (M + H) 3

399

Ex. No. compound name MS class
621 3-chioro-N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)methyl]-2-
fluorobenzamide 460 (M + H) -622 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyll-2,3-difluoro-4-methylbenzamide 458 (M + H) ->
623 2-chloro-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]-4-
fluorobenzamide 460 (M + H) 3
624 3-chIoro-N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]-2,4-
difluorobenzamide 478 (M + H) -i
625 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2'
yI]amino}cyC1-5hexyl)methyIl-2-(phenylthio)acetamide 454 (M + H) 3
626 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)methyl]-2-fluoro-3-
(trifluoromethyl)benzamide 494 (M + H)
627 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]-2-fluoro-5-
(trifluoromethyl)benzamide 494 (M + H) 3
628 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino)cyclohexy])methyll-2-phenylbutanamide 450 (M + H) 3
629 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino)cyclohexyl)methyll-2-(3-methoxypheny[)acetamide 452 (M + H) -i
630 N-[(cis-4-{[4-(dimethylamino)-5,6,7?8-tetrahydroquinazolin-2-
yI]amino)cyclohexyI)methyll-2-(4-fluorophenyl)acetamide 440 (M + H) 3
631 N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyll-2-(4-methoxyphenyl)acetamide 452 (M + H) 1
632 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yi]amino}cyclohexyl)methyl]-5-methyl-2-
(trifluoromethyI)-3-furamide 480 (M + H) 1
633 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllaminoicyC1-5hexyl)methyn-2,5-dimethyl-3-furamide 426 (M + H) 3
634 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ytlamino}cyc]ohexy])methyI]-2-ethoxybenzamide 452 (M + H) 3
635 3-chIoro-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyi)methyI]-4-
fluorobenzamide 460 (M + H)
636 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazo)in-2-
yllamino}cyclohexyl)methyl]-3-fIuoro-4-methylbenzamide 440 (M + H)
637 2-cyclopentyl-N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyllacetamide 414 (M + H) 3
638 N-[(cis-4-{[4-(dimethylamino)-5?6T7,8-tetrahydroquinazolin-2-
yIlamino}cyC1-5hexyl)methyI]-3,5-dimethoxybenzamide 468 (M + H) ->
639 4-cyano-N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-ynamino}cyclohexyl)methyl]benzamide 433 (M + H)
640 N-[(cis-4-{[4-(dimethy]amino)-5?6,7,8-tetrahydroquinazolin-2-
y!]amino}cyclohexyl)methyIl-3,5-bis(trifluoromethyl)benzamide 544 (M + H)

400

Ex. No. compound name MS class
641 (2E)-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yllamino}cvclohexvl)methyl]-3-(4-nitrophenyl)acrylamide 479 (M + H) 2
642 2-(2-bromophenyl)-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]acetamide 500 (M + H) 3
643 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexyl)methyll-4-fluoro-3-methylbenzamide 440 (M + H) 2
644 2-[(difluoromethyI)thio]-N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl"|amino}cyclohexyl)methynbenzamide 490 (M + H)
645 2,5-dichloro-N-[{cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]thiophene-3-
carboxamide 482 (M + H)
646 N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methyll-2-(propylthio)nicotinamide 483 (M + H) 1
647 l-benzy]-3-tert-butyl-N-[(cis-4-{[4-tdimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]-lH-
pyrazole-5-carboxamide 544 (M + H)
648 3-tert-butyl-N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]-l-methyl-
1 H-pyrazole-5-carboxamide 468 (M + H) 3
649 (2E)-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-ynamino}cyclohexyl)methyll-2-methyl-3-phenylacrylamide 448 (M + H)
650 5-bromo-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yllamino}cyclohexyl)-methyllnicotinamide 487 (M + H) 3
651 N-[(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino} cyclohexyl)methy I]-2-( 1 -naphthyi)acetamide 472 (M + H)
652 l-tert-butyl-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyI]-5-methyl-
lH-pyrazole-3-carboxamide 468 (M + H) j
653 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methytl-l-benzothiophene-3-carboxamide 464 (M + H) 3
654 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyIlbiphenyl-4-carboxamide 484 (M + H) 3
655 2-bromo-N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazoIin-2-yI]amino}cyclohexyI)methyllbenzamide 486 (M + H) 3
656 2,6-dichloro-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)methyI]benzaraide 476 (M + H) 2
657 N-[tcis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methyl]-2-iodobenzamide 534 (M + H) 3
658 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino)cyclohexyl)methyl]-2-methylbenzamide 422 (M + H) 3
659 2,3-dichIoro-N-[(cis-4-{[4-(dimethylamino)-5s6,7,8-
tetrahydroquinazolin-2-ynamino}cyc]ohexyl)methyl]benzamide 476 (M + H) 3
660 2-chloro-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazoIin-2-yllamino}cyclohexyl)methyll-5-fluorobenzamide 460 (M + H)
661 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methyl]-9-oxo-9H-fluorene-4-carboxamide 510 (M + H)
662 N-[{cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methyn-2,3,6-trifluorobenzamide 462 (M + H) 3

401

Ex. No. compound name MS class
663 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yi]amino}cyclohexyI)methYll-2,3-difluorobenzamide 444 (M + H) 3
664 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)methyll-2,6-difluorobenzamide 444 (M + H)
665 N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyl)methyl]-2-fluoro-6-(trifIuoromethyl)-
benzamide 494 (M + H) 3
666 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y!]amino}cyclohexyl)methyl]-2,4,6-trimethylbenzamide 450 (M + H) 2
667 2-chioro-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)methyl]-6-
fluorobenzamide 460 (M + H) 2
668 2,4J6-trichloro-N-[(cis-4-{[4-(dimethylamino)-5,6,7!8-
tetrahydroquinazolin-2-yllamino}cyC1-5hexyl)methyIlbenzamide 510 (M + H) 1
669 (2E)-3-(2-chlorophenyl)-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyI)methyllacrylamide 468 (M + H) 3
670 6-chloro-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)methyl]-2-fluoro-3-
methylbenzamide 474 (M + H) -i
671 2-chIoro-N-[(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydro-
quinazolin-2-yI]amino}cyclohexyl)methyl]-3,6-
difluorobenzamide 478 (M + H) 3
672 N-[(cis-4-{[4-(dimethylamino)-5,6,758-tetrahydroquinazolin-2-
yl]amino}cyclohexyi)methyl]-2,3-dimethylbenzamide 436 (M + H) 3
673 5-bromo-N-(cis-4-{[4-(dimethylamino)quinoIin-2-
yl]amino}cyclohexyI)thiophene-2-carboxamide 473 (M + H) 2
674 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(2,3,6-trichlorophenyI)acetamide 505 (M + H)
675 2-(2-chloro-4-fluorophenyl)-N-(cis-4-{[4-
(dimethylamino)quinolin-2-yIlamino}cyC1-5hexyl)acetamide 455 (M + H) ">
676 5-(4-chloro-2-nitrophenyl)-N-(cis-4-{[4-
(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-furamide 534 (M + H) 2
677 5-chIoro-N-(cis-4- {[4-(dimethylamino)quinolin-2-
yI]amino}cyclohexyl)thiophene-2-carboxamide 429 (M + H) 2
678 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
2,3-diphenylpropanamide 493 (M + H) ->
679 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-
(2-hydroxyphenyl)propan amide 433 (M + H)
680 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-5-
iodo-2-furamide 505 (M + H) 1
681 N-(cis-4-{[4-(dimethylamino)quino!in-2-yl]amino}cyclohexyl)-2-
(2-iodophenyl)acetamide 529 (M + H) 2
682 N-(cis-4-{[4-(dimethylamino)qumoIin-2-yl]amino}cyclohexyi)-2-
(5-methoxy-2-methyl-lH-indol-3-yl)acetamide 486 (M + H) 2
683 (2E)-N-(cis-4- {[4-(dimethy lam ino)qui noli n-2-
yl]amino}cyclohexyl)-3-(3-nitrophenyl)acrylamide 460 (M + H) 2
684 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-3-
oxoindane-1 -carboxamide 443 (M + H)

402

Ex. No. compound name MS class
685 2-benzyl-N-tcis-4-{[4-(dimethyiamino)quinolin-2-
yr|amino}cyclohexyl)benzaniide 479 (M + H) ->
686 2,2-bis(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
Yl~|amino}cyclohexy])acetamide 547 (M + H) 2
687 N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-5-
(4-methyl-2-nitrophenyl)-2-furamide 514 (M + H)
688 N-(cis-4-{[4-(dimethylamino)quinoiin-2-yl]amino}cyclohexyl)-5-
nitrothiophene-2-carboxamide 440 (M + H) 1
689 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-
methy 1 -4-n itroben zam ide 448 (M + H) 1
690 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-
methoxv-4-nitrobenzamide 464 (M + H) 1
691 l-benzyl-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yI]amino}cyclohexyl)-lH-indoIe-3-carboxamide 518 (M + H)
692 3-acetyl-N-(cis-4-{[4-(dimethylamino)quinoIiiv2-
yllamino}cyclohexyl)benzamide 431 (M + H) ■->
693 (2R)-2-benzoyl-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cvclohexyl)cyclohexanecarboxamide 499 (M + H) 3
694 5-bromo-N-(cis-4- {[4-(dimethy lamino)quinolin-2-
yllamino} cyC1-5hexyI)-2-furamide 457 (M + H) 1
695 3-cyclohexyl-N-(cis-4- {[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)propanamide 423 (M + H)
696 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-2-
[(4-methvIpynmidin-2-yl)thiolacetamide 451 (M + H)
697 5-(4-chIorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)-2-furamide 489 (M + H) 3
698 3-(3,4-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyt)propanamide 485 (M + H) J
699 2-(3,4-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino} cyclohexyl)acetamide 471 (M + H)
700 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-
(4-hydroxy-3,5-dimethoxyphenyl)acetamide 479 (M + H) 3
701 4,5-dibromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)thiophene-2-carboxamide 551 (M + H) 2
702 2-(3,5-dimethoxyphenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-
2-yl]amino) cyclohexyl)acetamide 463 (M + H) 3
703 2-(3,5-di4ert-butyl-4-hydroxyphenyl)-N-(cis-4-{[4-
(dimethylamino)quinolin-2-yl]amino}cyclohexyl)acetamide 531 (M + H) 3
704 N-2~,N-6~-dibenzoyl-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)lysinamide 621 (M + H) 3
705 3-(dimethylatnino)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)benzamide 432 (M + H)
706 4,5-dibromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyC1-5hexyl)-2-furamide 535 (M + H) 1
707 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-
(4-fluorophenyl)-4-oxobutanamide 463 (M + H)
708 N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-2-
{2-fluorobiphenyl-4-yl)propanamide 511 (M + H)

403

Ex. No. compound name MS class
709 tert-butyl {(1 S>l-[( 1-benzyl-lH-imidazol-4-yl)methyl]-2-[(cis-4-
{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)amino]-2-
oxoethy I} carbamate 612 (M + H) 3
710 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
f4-( 1-oxo-l, 3-d ihydro-2H-isoindoI-2-yl)phenyl]propanamide 548 (M + H)
711 N-{cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(lH-indol-3-yl)acetamide 442 (M + H) 1
712 N-(cis-4-{[4-(dimethylamino)quinolin-2-yljamino}cyclohexyl)-2-
(5-methyl-2-phenyl-l,3-thiazol-4-yl)acetamide 500 (M + H) ">
713 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(6-methoxy-3-oxo-2,3-dihydro-1 H-inden-1 -yl)acetamide 487 (M + H) "i
714 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-2-
{l-[(4-methoxybenzyl)thio]cyclohexyl}acetamide 561 (M + H)
715 N-(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}cyclohexyl)-2-
(7-methoxy-2-oxo-2H-chromen-4-yl)acetamide 501 (M + H) 3
716 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-
(lH-indol-3-yI)-4-oxo-4-phenylbutanamide 560 (M + H) 2
717 4-(4-bromophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)-2-(lH-indol-3-yl)-4-oxobutanamide 638 (M + H)
718 N-(cis-4- {[4-( dimethyl am in o)quinolin-2-yl] ami no} cyclohexyl)-
3,5-dimethyl-2-[({[4(trifluoromethoxy)phenyl]amino}-
carbony l)amin o]benzam ide 635 (M + H)
719 3,5-dichloro-N-(cis-4-{[4-(dimethylamino)qumolin-2-
yl]amino}cyc!ohexyl)-2-[(3-phenylprop-2-
ynoyl)aminolbenzamide 600 (M + H)
720 4-(4-tert-butylphenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
ynamino}cyclohexyl)-2-(7-ethyl-lH-indol-3-yl)-4-oxobutanamide 644 (M + H) -»
721 4-(4-tert-butylpheny l)-N-(cis-4- {[4-(dimethylamino)quinolin-2-
y l]amino} cyclohexyl)-2-( 1 -methyl-1 H-indol-3-
yl)-4-oxobutanamide 630 (M + H) -1
722 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(1 -methy 1-1 H-indol-3-yI)-4-(4-methylpheny l)-4-oxobutanamide 588 (M + H)
723 N-(2,4-dichlorophenyI)-2-{2-[(cis-4-{[4-
(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)amino]-2-
oxoethyljbenzamide 590 (M + H) 3
724 N-(cis-4- {[4-(dimethylamino)quinolin-2-y l]amino} cyclohexyl)-2-
methyl-1 -(3-morpholin-4-yipropyl)-5-phenyl-1H-
py rro le-3 -c arboxam ide 595 (M + H)
725 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-
(4-nitrophenyl)butanamide 476 (M + H) 3
726 (2E)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)-3-(2-nitrophenyl)acrylamide 460 (M + H)
727 N-(cis-4-{[4-(dimethy!amino)quinoIin-2-yl]amino}cyclohexyl)-2-
(3-phenoxyphenyI)acetamide 495 (M + H) 3
728 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(4-ph e noxypheny 1 )acetam ide 495 (M + H)
729 N-(cis-4-{[4-(dimethylamino)quinolin-2-yi]amino}cyclohexyl)-2-
(2-phenyI-1 H-indoI-3-y l)acetamide 518 (M + H) 2

404

Ex. No. compound name MS class
730 N2-benzoyl-N5-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)-N 1 ,N 1 -dipropylglutamamide 601 (M + H) ~i
731 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-3-
phenoxybenzamide 481 (M + H) ->
732 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-2-
(2-phenylethyl)benzamide 493 (M + H) 3
733 3-benzoyl-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)benzamide 493 (M + H)
734 N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyc!ohexyI)-2-
(ethylthio)-2,2-dipheny!acetamide 539 (M + H) ->
735 2-[(2-cyanophenyl)thio]-N-(cis-4-{[4-(dimethylamino)quinoIin-2-
y]]amino}cyclohexyl)benzamide 522 (M + H) -i
736 2-[4-(benzyioxy)-3-methoxypheny]]-N-(cis-4-{[4-
(dimethylamino)quinolin-2-yllamino}cyclohexyl)acetamide 539 (M + H) 3
737 N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexyl)-
N'-r( 1R)-1 -(1 -naphthyl)ethy Uphthalamide 586 (M + H)
738 (2S)-2-(3-benzoylphenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-
2-yl]amino}cyclohexyl)propanamide 521 (M + H)
739 N'-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
N,N-bis[( 1 S> 1 -phenylethyllphthalamide 640 (M + H) 3
740 (2S)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)-2-(2-fluorobiphenyl-4-yl)propanamide 511 (M + H)
741 2-[(4-chlorobenzyl)thio]-4-(4-chlorophenyl)-N-(cis-4-{[4-
(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-
4 -oxob utanam i de 635 (M + H) 3
742 2-[(4-chlorobenzyl)thio]-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)-4-(4-methylphenyl)-4-oxobutanamide 615 (M + H) *>
743 N-(cis-4-{[4-(dimethylamino)quino!in-2-yl]amino}cyclohexyl)-2-
{(lE)-5-fluoro-2-methyl-l-[4-(methylsulfinyl)benzylidene]-lH-
inden-3-vl}acetamide 623 (M + H) 3
744 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
[4-(2-thienylcarbonyl)phenyllpropanamide 527 (M + H) 3
745 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-4-
oxo-4-(2-thienyI)butan amide 451 (M + H) -i
746 N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-4-
(2-thienyl)butanamide 437 (M + H) 3
747 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(2,4,6-trichIorophenoxy)acetamide 521 (M + H) 2
748 2-[5-(benzyloxy)-lH-indol-3-yl]-N-(cis-4-{[4-
(dimethylamino)quinolin-2-ynamino}cyclohexyl)acetamide 548 (M + H) 3
749 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(1 -naphthoyl)benzamide 543 (M + H) 3
750 3-(benzyloxy)-N-(cis-4-{[4-(dimethy!amino)quinolin-2-
yl]amino)cyclohexyl)-4-methoxybenzamide 525 (M + H) 2
751 N-tcis-4-{[4-(dimethyIamino)quinoIin-2-yl]amino}cyclohexyl)-2-
rnethyl-1,5-dipheny 1-1 H-pyrrole-3-carboxamide 544 (M + H)

405

Ex. No. compound name MS class
752 l-{2-[(2-chloro-6-fluorobenzyl)thio]ethyl}-N-(cis-4-{[4-
(dimethyiamino)quinolin-2-yl]amino}cyC1-5hexyl)-2-methyl-5-
pheny 1-1 H-pyrroIe-3-carboxamide 670 (M + H) -i
753 N-{cis-4-{[4-(dimethylamino)quinolin-2-
y]]amino)cyC1-5hexyl)anthracene-9-carboxamide 489 (M + H) 3
754 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyi)-2-
phenoxybenzamide 481 (M + H) 2
755 N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyC1-5hexyl)bipheny]-2-carboxamide 465 (M + H)
756 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-
3,3-diphenyIpropanamide 493 (M + H) 3
757 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
phenylquinoline-4-carboxamide 516 (M + H) 2
758 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyc)ohexyl)-
N'-[(lS)-l-phenylethyllphthalamide 536 (M + H) ^>
759 N-(cis-4-{[4-(dimethyiamino)quinolin-2-yI]amino}cyclohexyl)-2-
(4-methylbenzoyl)benzamide 507 (M + H)
760 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
(phenoxymethyl)benzamide 495 (M + H) J
761 2-[4-(4-chIorophenyl)-2-phenyI-1,3-thiazol-5-yl]-N-(cis-4- {[4-
(dimethylamino)quinolin-2-yllamino}cyclohexyl)acetamide 596 (M + H) -*
762 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-l-
r(4-methylphenyl)sulfonyl]-1 H-pyrrole-3-carboxamide 532 (M + H) J
763 N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyI)-5-
(3-nitrophenyl)-2-furamide 500 (M + H) 1
764 3-chloro-N-(cis-4-{[4-(dimethyIamino)quinolin-2-
yl]amino}cyclohexyI)-4-(methylsulfonyl)thiophene-2-
carboxamide 507 (M + H)
765 3-ch!oro-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexy!)-4-(isopropylsulfonyl)-5-
(methylthio)thiophene-2-carboxamide 581 (M + H)
766 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-
iodo-4-(isopropylsulfonyl)-5-(methylthio)thiophene-2-
carboxamide 673 (M + H) 3
767 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-5-
nitrothiophene-3-carboxamide 440 (M + H) 1
768 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-l-
methyl-4-nitro-lH-pyrrole-2-carboxamide 437 (M + H) 1
769 N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-l-
(phenylsuIfonyl)-lH-indole-3-carboxamide 568 (M + H)
770 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-
nitrobenzamide 434 (M + H) 1
771 N-(cis-4-{[4-(dimethylamino)quino]in-2-yI]amino}cyclohexyI)-2-
methoxy-4-nitrobenzamide 464 (M + H) 2
772 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-3-
fluoro-4-(tri fl uorom ethy 1) benzam i de 475 (M + H) 1
773 N-(cis-4-{[4-(dimethy lamino)quinoIin-2-y ljamino} cyclohexyi)-2-
fluoro-4-nitrobenzamide 452 (M + H) 3

406

Ex. No. compound name MS class
774 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
3,5-dimethyl-4-nitrobenzamide 462 (M + H) 2
775 N-(cis-4-{[4-(dimethyIamino)quinolin-2-y]]amino}cyclohexy])-2-
mesityl-2-oxoacetamide 459 (M + H) 2
776 N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyC1-5hexyl)quinoline-3-carboxamide 440 (M + H)
111 N-(cis-4-{[4-(dimethylamino)quinolin-2-y]]amino}cyclohexyl)-2-
methoxy-2-phenyIacetamide 433 (M + H)
778 N-(cis-4-{[4-(dimethyIamino)quinoiin-2-yl]amino}cyclohexyI)-
l,2,3,4-tetrahydronaphthalene-2-carboxamide 443 (M + H) 3
779 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
l,3-benzothiazole-6-carboxamide 446 (M + H) ->
780 5-chloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)-2-hydroxybenzamide 439 (M + H) 2
781 2-chloro-N-(cis-4-{[4~(dimethylamino)quinoIin-2-
yl]amino}cyclohexyl)-5-(methyithio)ben2amide 469 (M + H) 3
782 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyI)-7-
methoxy-l-benzofuran-2-carboxamide 459 (M + H) 3
783 2-amino-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)-3-methylbenzamide 418 (M + H) 3
784 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-
hydroxy-3,5-dimethoxybenzamide 465 (M + H)
785 N-(cis-4-{[4-(dimethyIamino)quinolin-2-
yllamino}cyclohexyl)quinoline-4-carboxamide 440 (M + H)
786 2-(allylthio)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)nicotinamide 462 (M + H)
787 3,5-di-tert-butyl-N-(cis-4-{[4-(dimethylamino)quinoIin-2-
vI]amino}cyclohexyl)-4-hydroxybenzamide 517 (M + H)
788 5-bromo-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyllthiophene-2-carboxamide 487 (M + H)
789 N-[(cis-4- {[4-(dimethy lamino)quinolin-2-
yllamino}cyclohexyl)methyll-2-f2,3.6-trichlorophenyl)acetamide 519 (M + H) I
790 2-(2-chloro-4-fluorophenyl)-N-[(cis-4-{[4-(dimethylamino)-
quinoiin-2-yIlamino}cyC1-5hexyl)-methyllacetamide 469 (M + H) 3
791 5-(4-chloro-2-nitrophenyl)-N-[(cis-4-{[4-(dimethylamino)-
quinoIin-2-yIlamino)cyclohexyl)methyl]-2-furamide 548 (M + H) 3
792 5-chloro-N-[(cis-4-{[4~(dimethylamino)quinolin-2-
yllamino)cyC1-5hexyl>methyl]thiophene-2-carboxamide 443 (M + H)
793 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyI)methyIl-2,3-diphenyIpropanamide 507 (M + H)
794 N-[(cis-4-{[4-(dimethyIamino)quinoIin-2-
yllamino}cyC1-5hexy!)methyl]-3-(2-hydroxyphenvl)propanamide 447 (M + H)
795 N-[(cis-4- {[4-(dimethyIamino)quinolin-2-
yllamino}cyclohexyI)methyl]-5-iodo-2-furamide 519 (M + H)
796 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methy]]-2-(2-iodophenyl)acetamide 543 (M + H)
797 (2E)-N-[(cis-4-{[4-(dimethylamino)quinoIin-2-
yllamino}cyclohexyl)methyl]-3-(3-nitrophenyI)acrylamide 474 (M + H) 2

407

Ex. No. compound name MS class
798 N-[(cis-4~{[4~(dimethyIamino)quinolin'2-
yl]amino}cyclohexyl)methyl]-3-oxoindane-l-carboxamide 457 (M + H)
799 2-benzyI-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyllbenzamide 493 (M + H) 3
800 2,2-bis(4-chIorophenyl)-N-[(cis-4-{[4-(dimethyiamino)quinolin-
2-yl]amino}cyclohexyl)methyl]acetamide 561 (M + H)
801 N-[(cis-4-{[4-(dimethylamino)quino!in-2-yl]amino}cyclohexyl)-
methyl]-5-(4-methyI-2-nitrophenyl)-2-furamide 528 (M + H) 3
802 N-[(cis-4-{[4-(dimethylamino)quinoiin-2-
yl]amino)cyclohexyI)methyll-5-nitrothiophene-2-carboxamide 454 (M + H)
803 N-[(cis-4-{[4"(dimethylamino)quinolin-2-
yI]amino}cyclohexyl)methyll-3-methyI-4-nitrobenzamide 462 (M + H)
804 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
y!lamino)cyclohexy])methyl]-3-methoxy-4-nitrobenzamide 478 (M + H) 3
805 l-benzyl-N-[(cis-4-{[4-(dimethyIamino)quinolin-2-
yl]amino}cyclohexyl)methyll-lH-indole-3-carboxamide 532 (M + H)
806 2-cyclohex-1 -en-1 -y I-N-[(cis-4- {[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methynacetamide 421 (M + H) 3
807 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyl]-4-(4-ethoxyphenyl)-2-(3-methyl-5-
oxo-l-phenyl-4,5-dihydro-lH-pyrazol-4-yl)-4-oxobutanamide 675 (M + H) 3
808 N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
methyll-2-[2-(trifluoromethoxy)phenvllacetamide 501 (M + H) 3
809 4-(benzyIoxy)-N-[(cis-4-{[4-(dimethyiamino)quinolin-2-
yllamino)cyclohexyl)methyl]-3,5-dimethyibenzamide 537 (M + H) 3
810 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyC1-5hexyl)methyll-9H-xanthene-9-carboxamide 507 (M + H)
811 2-(l-benzothien-3-yl)-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyllacetamide 473 (M + H) 3
812 5-bromo-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-
y!lamino}cyclohexyl)thiophene-2-carboxamide 424 (M + H) 3
813 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexyl)-
2-(2,3,6-trichIorophenyl)acetamide 456 (M + H) 3
814 2-{2-chlor*>4'fiuorophenyl)-N-(cis-4- {[4-
(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)acetamide 406 (M + H)
815 5-(4-chloro-2-nitrophenyl)-N-(cis-4-{[4-
(dimethylamino)pyrimidin-2-ynamino}cyclohexyl)-2-furamide 485 (M + H) 1
816 5-chIoro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yI]ammo)cyC1-5hexyt)thiophene-2-carboxamide 380 (M + H) 3
817 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2,3-dipheny!propanamide 444 (M + H) 3
818 N-(cis-4-{[4-(dimethy!amino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
3-(2-hydroxvphenyl)propanamide 384 (M + H)
819 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
5-iodo-2-furamide 456 (M + H) 2
820 N-(cis-4-{[4-(dimethylamino)pyrimidin'2-yl]amino}cyclohexyl)-
2-(2-iodophenyI)acetamide 480 (M + H) 3

408

Ex. No. compound name MS class
821 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(5-methoxy-2-methyl-lH-indol-3-yl)acetamide 437 (M + H) ->
822 (2E)-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl]amino}cyclohexyI)-3-(3-nitrophenyl)acrylamide 411 (M + H) ->
823 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
3-oxoindane-1 -carboxamide 394 (M + H)
824 2-benzyl-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyclohexyt)benzamide 430 (M + H) 3
825 2,2-bis(4-chIorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-
2-yllamino} cyclohexy ])acetamide 498 (M + H)
826 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexy I)-
5-(4-methyI-2-nitrophenyl)-2-furamide 465 (M + H) 2
827 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexy 1)-
5-nitrothiophene-2-carboxamide 391 (M + H) 2
828 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
3-methvl-4-nitrobenzamide 399 (M + H) 2
829 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyI)-
3 -methoxy-4-n itrobenzam i de 415 (M + H) 1
830 1 -benzyl-N-(cis-4- {[4-(dimethy!amino)pyrimidin-2-
yl]amino)cyclohexyl)-lH-indole-3-carboxamide 469 (M + H) 2
831 3-acetyl-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)benzamide 382 (M + H) 2
832 (2R)-2-benzoyl-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)cyclohexanecarboxamide 450 (M + H) 3
833 5-bromo-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cYclohexyl)-2-furamide 408 (M + H) 1
834 3-cyclohexyi-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyc]ohexyl)propanamide 374 (M + H) 3
835 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-[(4-methylpyrimidin-2-yI)thiolacetamide 402 (M + H)
836 5-(4-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexy!)-2-furamide 440 (M + H) 1
837 3-(3,4-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)propanamtde 436 (M + H) 3
838 2-(3,4-dichloropheny[)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino)cyclohexyl)acetamide 422 (M + H)
839 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(4-hydroxy-3,5-dimethoxyphenyl)acetamide 430 (M + H)
840 4)5-dibromo-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)thiophene-2-carboxamide 501 (M + H) 2
841 2-(3,5-dimethoxyphenyI)-N-(cis-4-{[4-
(dimethylamino)pyrimtdin-2-yllamino}cyclohexyI)acetamide 414 (M + H)
842 2-(3,5-di-tert-butyi-4-hydroxyphenyi)-N-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)acetamide 482 (M + H) 1
843 N2,N6-dibenzoyl-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)Iysinamide 572 (M + H) 2
844 3-(dimethylamino)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)benzamide 383 (M + H) 2

409

Ex. No. compound name MS class
845 4,5-dibromo-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyclohexyl)-2-furamide 486 (M + H) 1
846 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-
4-(4-fluorophenyl)-4-oxobutanamide 414 (M + H)
847 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
2-(2-fluorobiphenyl-4-yl)propanamide 462 (M + H) -i
848 l-benzyl-Nalpha-(tert-butoxycarbonyl)-N-
(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
L-histidinamide 563 (M + H) ->
849 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-[4-(l-oxo-l,3-dihydro-2H-isoindol-2-yI)phenyI]propanamide 499 (M + H)
850 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(lH-indol-3-yl)acetamide 393 (M + H) 2
851 N-(cis-4- {[4-(dimethy lamino)pyrimidin-2-y l]amino} cyclohexyl)-
2-(5-methyl-2-phenyl-l,3-thiazol-4-yl)acetamide 451 (M + H) 2
852 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(6-methoxy-3-oxo-2,3-dihydro-1 H-inden-1 -yl)acetamide 438 (M + H) t
853 N-(cis-4- {[4-(dimethyl ami no)pyrimidin-2-yl]amino} cyclohexy 1)-
2-{l-f(4-methoxybenzyl)thiolcyclohexyl}acetamide 512 (M + H) 3
854 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetamide 452 (M + H) ->
855 N-(cis-4- {[4-(dimethy lamino)pyrimidin-2-yl]amino} cyclohexy 1)-
2-(lH-indol-3-yl)-4-oxo-4-phenylbutanamide 511 (M + H) 1
856 4-(4-bromophenyI)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)-2-(lH-indol-3-yl)-4-oxobutanamide 589 (M + H) 2
857 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
3,5-dimethyl-2-[({[4(trifluoromethoxy)phenyl]amino}carbonyl)-
amino]benzamide 586 (M + H) 3
858 3,5-dichloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
y!]amino}cyclohexyl)-2-[(3-pheny!prop-2-
ynoyl)aminolbenzamide 551 (M + H) 2
859 3-[2-(4-bromophenyl)-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-lH-
indol-l-yI]-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-
y l]amino) cvclohexyl)benzamide 655 (M + H) ">
860 4-(4-tert-butylpheny I)-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyI)-2-(7-ethv!-lH-indol-3-yI)-4-oxobutanamide 595 (M + H) 3
861 4-(4-tert-butylphenyl)-N-(cis-4-{[4~(dimethylamino)pyrimidin-2-
y l]amino} cyclohexyl)-2-( 1 -methyl-1 H-indol-3-y l)-4-
oxobutanamide 581 (M + H)
862 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(l-methyl-lH-indol-3-yI)-4-(4-methyIphenyl)-4-oxobutanamide 539 (M + H) 1
863 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-methy 1-1 -(3-morphoIin-4-y lpropyI)-5-phenyl-1 H-pyrroIe-
3-carboxamide 546 (M + H) 2
864 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
4-(4-nitrophenyl)butanamide 427 (M + H) 2
865 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-[(3-nitropyridin-2-yI)thio]acetamide 432 (M + H) -

410

Ex. No. compound name MS class
866 (2E)-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyC1-5hexyl)-3-(2-nitrophenyI)acrylamide 411 (M + H) -i
867 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
2-{3-phenoxyphenyl)acetamide 446 (M + H) 3
868 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(4-phenoxyphenyl)acetamide 446 (M + H) ->
869 N-fcis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-(2-phenyl-1 H-indol-3-yl)acetamide 469 (M + H) 1
870 lN2-benzoyI-N5-(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino)cyclohexy!)-Nl,Nl-dipropylglutamamide 552 (M + H) 2
871 N-(cis-4- {[4-(dimethy lamino)pyrimidin-2-yl]amino} cyclohexyl)-
3-phenoxybenzamide 432 (M + H) 2
872 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexyl)-
2-(2-phenyIethyl)benzamide 444 (M + H) 3
873 3-benzoyl-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)benzamide 444 (M + H) 2
874 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
2-(ethylthio)-2,2-diphenylacetamide 490 (M + H) 1
875 2-[(2-cyanophenyl)thio]-N-(cis-4-{[4-(dimethylamino)pyrimidin-
2-yl]amino}cyclohexyl)benzamide 473 (M + H)
876 2-[4-(benzyloxy)-3-methoxyphenyI]-N-(cis-4-{[4-
(dimethyIamino)pyrimidin-2-yllamino}cyclohexyl)acetamide 490 (M + H) 3
877 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
N'-r(lR)-l-(l-naphthyl)ethyllphthalamide 537 (M + H) 2
878 (2S)-2-(3-benzoylphenyl)-N-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yllamino}cyclohexyl)propanamide 472 (M + H) 2
879 N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N,N-bisf( 1S)-1 -pheny lethyllphthalamide 591 (M + H) I
880 (2S)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)-2-(2-fluorobiphenyi-4-yl)propanamide 462 (M + H) 3
881 2-[(4-chlorobenzy l)th io]-4-(4-chlorophenyl)-N-(cis-4- {[4-
(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
4-oxobutanamide 586 (M + H) 3
882 2-[(4-chlorobenzyl)thio]-N-(cis-4-{[4-(dimethylamino)pyrimidin-
2-yl]amino}cyC1-5hexyl)-4-(4-methyIphenyI)-4-oxobutanamide 566 (M + H)
883 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexyl)-
2- {(lE)-5-fluoro-2-methyl-1 -[4-(methylsulfinyl)benzyIidene]-1H-
inden-3-yl}acetamide 574 (M + H) 2
884 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyI)-
2-[4-(2-thienylcarbonyl)phenyl]propanamide 478 (M + H) 2
885 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
4-oxo-4-(2-thienyl)butanamide 402 (M + H) ■■>
886 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
4-(2-thienyl)butanamide 388 (M + H) ->
887 2-[5-(benzyloxy)-lH-indoi-3-yl]-N-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yIlamino}cyclohexyl)acetamide 499 (M + H) 3
888 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-y ljamino} cyclohexy 1)-
2-fl-naphthoyl)benzamide 494 (M + H)

411

Ex. No. compound name MS class
889 3-(benzyIoxy)-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl]amino}cyclohexy])-4-methoxybenzamide 476 (M + H) 1
890 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyi)-
2-methyI-I,5-diphenyi-IH-pyrrole-3-carboxamide 495 (M + H) 1
891 l-{2-[(2-ch!oro-6-fluorobenzyl)thio]ethyl}-N-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-2-methyI-5-
phenyl-1 H-pyrrole-3-carboxamide 621 (M + H) 1
892 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)anthracene-9-carboxamide 440 (M + H)
893 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yi]amino}cyC1-5hexyl)-
2-phenoxybenzamide 432 (M + H) 2
894 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cvclohexyl)biphenyI-2-carboxamide 416 (M + H) 3
895 N-(cis-4-{[4-tdimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-
3,3-diphenylpropanamide 444 (M + H)
896 N-{cis-4- {[4-(dimethy lamino)pyrimidin-2-yl]amino} cyclohexyl)-
2-phenylquinoline-4-carboxamide 467 (M + H) 2
897 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
N'-f( 1S)-1 -phenylethy llphthalamide 487 (M + H) 3
898 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyI)-
2-{4-methylbenzoyl )benzamide 458 (M + H) 3
899 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyclohexyl)-
2-( phe noxy methyl )benzam id e 446 (M + H)
900 2-[4-(4-chIorophenyI)-2-phenyl-l,3-thiazol-5-yl]-N-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)acetamide 547 (M + H) 1
901 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexy!)-
l-("(4-methylphenyl)sulfonyl]-lH-pyrrole-3-carboxamide 483 (M + H) 2
902 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
5-(3-nitrophenyl)-2-furamide 451 (M + H) 2
903 3-chloro-N'(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)-4-(methy!sulfonyl)thiophene-
2-carboxamide 458 (M + H) 3
904 3-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yI]amino}cyC1-5hexyl)-4-(isopropylsulfonyl)-5-
(methylthio)thiophene-2-carboxamide 532 (M + H) 2
905 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyI)-
3-iodo-4-(isopropylsulfonyI)-5-(methylthio)thiophene-
2-carboxamide 624 (M + H) 2
906 N-(cis-4-{[4-{dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
5-nitrothiophene-3-carboxamide 391 (M + H) 1
907 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyI)-
I-methyl-4-nitro-lH-pyrrole-2-carboxamide 388 (M + H) 1
908 N-(cis-4-{[4-(drmethyiamino)pyrimidin-2-yl]amino}cyC1-5hexyI)-
1 -(phenylsulfonyl)-l H-indoIe-3 -carboxamide 519 (M + H)
909 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
4-nitrobenzamide 385 (M + H) 2
910 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-
2-m ethoxy-4 -nitrobenzam i de 415 (M + H) i

412

Ex. No. compound name MS class
911 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
3-fluoro-4-(trifluoromethy])benzamide 426 (M + H) ->
912 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexy I)-
2-fluoro-4-nitrobenzamide 403 (M + H) -i
913 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
3,5-dimethyI-4-nitrobenzamide 413 (M + H) 2
914 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-mesityl-2-oxoacetamide 410 (M + H) 2
915 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yI]amino}cyclohexyl)quinoline-3-carboxamide 391 (M + H)
916 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
2-methoxy-2-phenylacetamide 384 (M + H)
917 N-(cis-4-{[4-(dimethyJamino)pyrimidin-2-yl]amino}cyclohexyl)-
1,2,3,4-tetrahydronaphthalene-2-carboxamide 394 (M + H) ->
918 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
1,3-benzothiazole-6-carboxamide 397 (M + H) 3
919 5-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]arnino}cyclohexyl)-2-hydroxybenzamide 390 (M + H) 3
920 2-chIoro-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yI"|amino}cyclohexylV5-(methyIthio)benzamide 420 (M + H) 3
921 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-y ljamino} cyclohexyl)-
7-methoxy-]-benzofuran-2-carboxamide 410 (M + H) 3
922 2-amino-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyI)-3-methylbenzamide 369 (M + H)
923 2-(alIylthio)-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl"]amino}c"vclohexyl)nicotinamide 413 (M + H)
924 3,5-di-tert-butyl-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-
ynamino}cyclohexyl)-4-hydroxybenzamide 468 (M + H) 1
925 5-bromo-N-[(cis-4-{[4-{dimethylamino)pyrimidin-2-
yI]amino}cyclohexyl)methyllthiophene-2-carboxamide 438 (M + H) 3
926 N-[(cis-4- {[4-(dimethy Iamino)pyrimidin-2-
yllamino}cyC1-5hexyi)methyl]-2-(2,3,6-trichlorophenyl)acetamide 470 (M + H) 1
927 2-(2-chloro-4-fluorophenyl)-N-[(cis-4-{[4-(dimethylamino)-
pyrimidin-2-yi]ammo}-cyclohexyI)methyllacetamide 420 (M + H) 3
928 5-(4-chIoro-2-nitrophenyl)-N-[(cis-4-{[4-(dimethylamino)-
pynmidin-2-yIlamino}-cyclohexvl)methyn-2-furamide 499 (M + H) 3
929 5-chioro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyI)methyI]thiophene-2-carboxamide 394 (M + H) 3
930 N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl]amino}cyclohexyI)methyll-2,3-diphenylpropanamide 458 (M + H) 2
931 N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl]amino}cyctohexyI)methyl]-3-(2-hydroxyphenyl)propanamide 398 (M + H) 3
932 N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyclohexyl)methyIl-5-iodo-2-furamide 470 (M + H) 2
933 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
methyn-2-(5-methoxy-2-methyI-lH-indol-3-yl)acetamide 451 (M + H)
934 (2E)-N-[(cis-4- {[4-(dimethy Iamino)pyrimidin-2-
ynamino}cyclohexyI)methyn-3-(3-nitrophenyl)acryIamide 425 (M + H) 1

413

Ex. No. compound name MS class
935 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexYi)methyn-3-oxoindane-l-carboxamide 408 (M + H) 1
936 2-benzyl-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]benzamide 444 (M + H) 2
937 2,2-bis(4-chlorophenyl)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-
2-yl]amino}cyclohexyl)methyIlacetamide 512 (M + H) 1
938 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
methyI]-5-(4-methyl-2-nitrophenyI)-2-furamide 479 (M + H)
939 N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyC1-5hexyl)methyn-5-nitrothiophene-2-carboxamide 405 (M + H) ->
940 N-[(cis-4-{[4-(dimethylamino)pyrtmidin-2-
ynamino}cyclohexyI)methyI]-3-methvl^-nitrobenzamide 413 (M + H) 1
941 N-[fcis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyl]-3-methoxy-4-nitrobenzamide 429 (M + H) 1
942 l-benzyI-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyl]-lH-indole-3 943 2-cyclohex-l-en-l-yl-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyl]acetamide 372 (M + H) 3
944 N-[(cis-4-{[4-(dirnethyIamino)pyrimidin-2-
yl]amino}cyclohexyI)methyl]-4-(4-ethoxyphenyl)-2-(3-methyl-5-
oxo-l-phenyl-4,5-dihydro-lH-pyrazol-4-yl)-4-oxobutanamide 626 (M + H) 3
945 N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}-
cyC1-5hexyl)methy]]-2-[2-(trifluoromethoxy)phenyl]-
acetamide 452 (M + H) 1
946 4-(benzyloxy)-N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
ynamino}cyclohexyl)methyll-3,5-dimethylbenzamide 488 (M + H) ^
947 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyll-9H-xanthene-9-carboxamide 458 (M + H) 1
948 2-(l-benzothien-3-yl)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]acetamide 424 (M + H) 1
949 5-bromo-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amtno)cyclohexyl)-thiophene-2-carboxamide 478 (M + H) 2
950 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
ynaminoicyC1-5hexyl)-2-(2,3,6-trichlorophenyl)acetamide 510 (M + H) 2
951 2-(2-chIoro-4-fluorophenyl)-N-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)acetamide 460 (M + H) 1
952 5-(4-chIoro-2-nitrophenyI)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)-2-furamide 539 (M + H) 1
953 5-chloro-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydro-
quinazolin-2-yllamino}cyclohexyl)-thiophene-2-carboxamide 434 (M + H) 1
954 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexy!)-2,3-diphenylpropanamide 498 (M + H) 2
955 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-3-(2-hydroxyphenyl)propanamide 438 (M + H) 2
956 N-{cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino)cyclohexyl)-5-iodo-2-furamide 510 (M + H) 1
957 N-(cis-4-{[4-(dimethylamino>5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)-2-(2-iodophenyl)acetamide 534 (M + H) 2

414

Ex. No. compound name MS class
958 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)-2-(5-methoxy-2-methyl-lH-
indol-3-yl)acetamide 491 (M + H) 2
959 (2E)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-
2-yl]amino}cyclohexyI)-3-(3-nitrophenyl)acry]amide 465 (M + H) 3
960 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-3-oxoindane-l-carboxamide 448 (M + H) 2
961 2-benzyl-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazo]in-2-yI]amino}cvC1-5hexyl)benzamide 484 (M + H) 2
962 2,2-bis(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yIlamino}cyclohexyl)acetamide 552 (M + H) 1
963 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexyl)-5-(4-methyt-2-nitrophenyl)-2-furamide 519 (M + H) 2
964 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-5-nitrothiophene-2-carboxamide 445 (M + H) 1
965 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-3-methyI-4-nitrobenzamide 453 (M + H) 1
966 N-(cis-4-{[4-(dimethyiamino)-556,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-3-methoxy-4-nitrobenzamide 469 (M + H) 1
967 l-benzyl-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-y]lamino}cyC1-5hexyl)-lH-indole-3-carboxamide 523 (M + H) -»
968 3-acetyl-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino)cyclohexyl)benzamide 436 (M + H) 1
969 (2R)-2-benzoyl-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)-
cyclohexanecarboxamide 504 (M + H)
970 5-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-y!lamino}cyclohexyl)-2-furamide 462 (M + H) 1
971 3-cyclohexyI-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-ynamino}cyclohexyl)propanamide 428 (M + H) ^
972 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoiin-2-
yllamino}cyclohexyI)-2-[(4-methylpyrimidin-2-yl)thiolacetamide 456 (M + H) 2
973 5-(4-chIorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino)cyclohexyl)-2-furamide 494 (M + H) 1
974 3-(3,4-dichlorophenyI)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazoIin-2-yIlamino}cyclohexyI)propanamide 490 (M + H) 3
975 2-(3,4-dichIorophenyl)-N-{cis-4-{[4-(dimethyiamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino)cyclohexyl)acetamide 476 (M + H) 1
976 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyI)-2-(4-hydroxy-3,5-
dimethoxvphenyl)acetamide 484 (M + H) 1
977 4,5-dibromo-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)thiophene-2-
carboxamide 556 (M + H) 2
978 2-(3,5-dimethoxyphenyI)-N-(cis-4-{[4-(dimethy]amino)-5,6,7,8-
tetrahydroquinazolin-2-yt]amino}cyclohexyl)acetamide 468 (M + H)

415

Ex. No. compound name MS class
979 2-(3,5-di-tert-butyl-4-hydroxyphenyI)-N-(cis-4-{[4-
(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyl)acetamide 536 (M + H) ->
980 N2,N6-dibenzoyl-N-(cis-4-{[4-{dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yilamino}cyC1-5hexyl)Iysinamide 626 (M + H) 2
981 3-(dimethylamino)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino)cyclohexyl)benzamide 437 (M + H) 2
982 4,5-dibromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)-2-furamide 540 (M + H) 1
983 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-4-(4-fluorophenyl)-4-oxobutanamide 468 (M + H) 2
984 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-2-(2-fluorobiphenyl-4-yl)propanamide 516 (M + H) 2
985 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yljamino} cyclohexyI)-2-[4-( 1 -oxo-1,3-dihydro-2H-isoindol-2-
yl)phenyl]propanamide 553 (M + H) 2
986 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-(lH-indol-3-yl)acetamide 447 (M + H) 1
987 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino} cyclohexyl)-2-(5-methyI-2-phenyl-1,3-
th i azol -4-y I )acetam ide 505 (M + H) 3
988 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
y!]amino} cyclohexyl)-2-(6-methoxy-3-oxo-2,3-dihydro-1H-
inden-1 -y l)acetamide 492 (M + H) 3
989 N-(cis-4-{[4-(dimethylamino)-5,6,758-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-{l-[(4-methoxybenzyl)thio]-
cyclohexyljacetamide 566 (M + H)
990 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-(7-methoxy-2-oxo-2H-
chromen-4-yl)acetamide 506 (M + H) 1
991 N-tcis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)-2-(lH-indol-3-yl)-4-
oxo-4-phenylbutanamide 565 (M + H) 2
992 4-(4-bromophenyl)-N-(cis-4-{[4-(dimethylamino>5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyI)-2-(lH-indoI-3-yl)-
4-oxobutanamide 643 (M + H)
993 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yt]amino} cyclohexy l)-3,5-dimethyl-2-[( {[4-
(trifluoromethoxy)phenyl]amino}carbonyl)amino]benzamide 640 (M + H) 1
994 3,5-dichIoro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)-2-[(3-phenylprop-2-
ynoyl)aminolbenzamide 605 (M + H) 1
995 3-[2-(4-bromophenyl)-6,6-dimethyI-4-oxo-4,5,6,7-tetrahydro-lH-
indoI-l-yI]-N-(cis-4-{[4-(dimethylamino)-5;6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)benzamide 709 (M + H)
996 4-(4-tert-butylphenyl)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)-2-(7-ethyI-lH-
indol-3-yI)-4-oxobutanamide 649 (M + H) 1

416

Ex. No. compound name MS class
997 4-(4-tert-butylphenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)-2-(l-methyl-lH-
indol-3-yl)-4-oxobutanamide 635 (M + H)
998 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y l]amino} cyclohexy l)-2-(l -methyl-1 H-indol-3-yI)-4-(4-
methvlphenyl)-4-oxobutanamide 593 (M + H) 2
999 N-(2,4-dichlorophenyI)-2-{2-[(cis-4-{[4-(dimethylamino>5,6,7,8-
tetrahydroquinazol in-2-y l]amino} cyclohexyl)amino]-2-
oxoethy I} benzam ide 595 (M + H) 3
1000 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyl)-2-methyl-l-(3-morpholin-4-y]propyl)-5-
phenyl-1 H-pyrrole-3-carboxamide 600 (M + H) 1
1001 N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino)cyC1-5hexyl)-4-(4-nitrophenyl)butanamide 481 (M + H) 1
1002 (2E)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yllamino}cyclohexyl)-3-(2-nitrophenyI)acrylamide 465 (M + H) -i
1003 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-2-(3-phenoxyphenyl)acetamide 500 (M + H) 2
1004 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyctohexyl)-2-(4-phenoxyphenyl)acetamide 500 (M + H) 2
1005 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-2-(2-phenyl-lH-indol-3-yl)acetamide 523 (M + H) 1
1006 N2-benzoyl-N5-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-y l]amino} cyclohexyI)-N 1 ,N 1 -
d i propy 1 glutam am ide 606 (M + H) 1
1007 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-3-phenoxybenzamide 486 (M + H) 1
1008 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-(2-phenylethyl)benzamide 498 (M + H) 3
1009 3-benzoyl-N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-
tetrahydroquinazol in-2-y l]amino}cyclohexyl)benzamide 498 (M + H)
1010 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyC1-5hexyl)-2-(ethylthio)-2,2-dipheny!acetamide 544 (M + H) 2
1011 2-[(2-cyanophenyI)thio]-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-ynamino}cyc!ohexyl)benzamide 527 (M + H)
1012 2-[4-(benzyloxy)-3-methoxyphenyl]-N-(cis-4-{[4-
(dimethylamino)-5,6,7,8-tetrahydroquinazo!in-2-
yl]amino}cyclohexyl)acetamide 544 (M + H)
1013 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y Hamino} cyclohexyl)-N'-[{ 1R)-1 -(1 -naphthyl)ethy llphthalamide 591 (M + H) 3
1014 (2S)-2-t3-benzoylphenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahvdroquinazolin-2-yl]amino)cyC1-5hexyl)propan amide 526 (M + H)
1015 N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)-N,N-bis[(lS)-l-phenyIethyllphthalamide 645 (M + H) 1
1016 (2S)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yllamino}cyc]ohexyl)-2-(2-fluorobipheny]-4-yl)propanamide 516 (M + H) 2

417

Ex. No. compound name MS class
1017 2-[(4-chlorobenzyI)thio]-4-(4-chloropheny l)-N-(cis-4- {[4-
(d im ethy lam i n o)- 5,6,7,8 -tetrahyd roq u i nazo 1 i n -2 -
yI]amino)cyclohexyl)-4-oxobutanamide 640 (M + H) ->
1018 2-[(4-chlorobenzyl)thio]-N-(cis-4-{[4-(dimethylamino)-5,657,8-
tetrahydroquinazoIin-2-yl]amino}cyC1-5hexy])-4-(4-
methylphenyl)-4-oxobutanamide 620 (M + H) 2
1019 N-(cis-4-{[4-(dimethylamino)-5,637,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-{(lE)-5-fluoro-2-methyl-l-[4-
fmethylsu]finyl)benzyIidenel-lH-inden-3-y]}acetamide 628 (M + H) 1
1020 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyC1-5hexyl)-2-[4-(2-
th i eny I c arbon y l)pheny 11 propan am ide 532 (M + H) 2
1021 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-4-oxo-4-(2-thienyl)butanamide 456 (M + H)
1022 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-4-(2-thienyl)butanamide 442 (M + H)
1023 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-2-(2,4,6-trichlorophenoxy)acetamide 526 (M + H)
1024 2-[5-tbenzyloxy)-lH-indoI-3-yl]-N-tcis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazoIin-2-yI]amino}cyclohexyl)acetamide 553 (M + H)
1025 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyI)-2-( 1 -naphthoyl)benzamide 548 (M + H) 3
1026 3-(benzyloxy)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)-4-
methoxybenzamide 530 (M + H) 1
1027 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazo!in-2-
yl]amino}cyclohexyl)-2-methyl-l,5-diphenyl-lH-
pyrroIe-3-carboxamide 549 (M + H) 2
1028 l-{2-[(2-chloro-6-fluorobenzyl)thio]ethyl}-N-(cis-4-{[4-
(dimethy-Iamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexy l)-2-methy 1-5 -pheny 1-1 H-pyrrole-3 -carboxam ide 675 (M + H) 2
1029 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yi|amino}cyC1-5hexyl)anthracene-9-carboxamide 494 (M + H)
1030 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino)cyclohexyl)-2-phenoxybenzamide 486 (M + H) 1
1031 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yilamino}cyclohexyl)biphenyl-2-carboxamide 470 (M + H) 3
1032 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoiin-2-
yl]amino}cyclohexyl)-3,3-diphenylpropanamide 498 (M + H) ">
1033 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl}amino}cyclohexyl)-2-phenylquinoline-4-carboxamide 521 (M + H) 2
1034 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino) cyclohexy l)-N'-[( 1S)-1 -pheny Iethyl]phthalamide 541 (M + H)
1035 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino)cyclohexyl)-2-(4-methylbenzoyi)benzamide 512 (M + H)
1036 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin~2-
ynamino}cyclohexyl)-2-(phenoxymethyl)benzamide 500 (M + H)

418

Ex. No. compound name MS class
1037 2-[4-(4-chIorophenyl)-2-phenyl-l,3-thiazol-5-yl]-N-(cis-4-{[4-
(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
Yl]amino}cyclohexyl)acetamide 601 (M + H) ->
1038 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-l-[(4-methylphenyl)sulfonyl]-lH-pyrrole-
3-carboxamide 537 (M + H) -i
1039 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-5-(3-nitrophenyl)-2-furamide 505 (M + H) 2
1040 3-chIoro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)-4-(methylsulfonyl)thiophene-
2-carboxamide 512 (M + H)
1041 3-chloro-N tetrahydroquinazolin-2-yl]amino}cyclohexyI)-4-
(isopropylsulfonyl)-5-(methylthio)thiophene-2-carboxamide 586 (M + H) ->
1042 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyl)-3-iodo-4-(isopropylsulfonyl)-5-
fmethylthio)thiophene-2-carboxamide 678 (M + H)
1043 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-5-nitrothiophene-3-carboxamide 445 (M + H) 1
1044 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y 1] amino} eye lohexy 1)-1 -methy 1-4-nitro-1H-
pyrrole-2-carboxamide 442 (M + H) 1
1045 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y ljamino} cyclohexyl)-1 -(phenylsulfonyl)-
IH- indole-3 -carboxamide 573 (M + H) 3
1046 N-(cts-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino)cyC1-5hexyl)-4-nitrobenzamide 439 (M + H) "i
J
1047 N-(cis-4-{[4-(dimethylamino)-5,6,7,84etrahydroquinazolin-2-
yllamino}cyC1-5hexyl)-2-methoxy-4-nitrobenzamide 469 (M + H) 2
1048 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyC1-5hexyl)-3-fluoro-4-(trifluoromethyl)benzamide 480 (M + H) T
1049 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-fluoro-4-nitrobenzamide 457 (M + H) ■->
1050 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyC1-5hexyi)-3,5-dimethyl-4-nitrobenzamide 467 (M + H) 3
1051 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-2-mesityl-2-oxoacetamide 464 (M + H) ->
1052 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yllamino}cyclohexyl)-2-methoxy-2-phenylacetamide 438 (M + H) 2
1053 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino} cyclohexyl)-! ,2,3,4-tetrahydronaphthalene-
2-carboxamrde 448 (M + H) -i
1054 N-(cis-4-{[4-{dtmethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino} cyclohexyl)-1,3-benzothiazole-6-carboxamide 451 (M + H) 3
1055 5-chloro-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydro-
quinazolin-2-yIlamino}cyclohexyl)-2-hydroxybenzamide 444 (M + H) 1
1056 2-chloro-N-(cis-4-{[4-(dimethy!amino)-5,6,7,8-tetrahydro-
quinazolin-2-ynamino}cyctohexyI)-5-(methylthio)-benzamide 474 (M + H) 3

419

Ex. No. compound name MS class
1057 N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-7-methoxy-l-benzofuran-2-carboxamide 464 (M + H) 3
1058 2-amino-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)-3-methylbenzamide 423 fM + H)
1059 2-(allylthio)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)nicotinamide 467 (M + H) 3
1060 3,5-di-tert-butyi-N-{cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)-4-
hydroxybenzamide 522 (M + H) ->
1061 5-bromo-N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]thiophene-2-
carboxamide 492 (M + H) 3
1062 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methyl]-2-(2,3,6-trichlorophenyl)acetamide 524 (M + H) 2
1063 2-(2-chloro-4-fluorophenyl)-N-[(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazoHn-2-yI]amino}cyclohexyl)methyl]-
acetamide 474 (M + H)
1064 5-(4-chloro-2-nitrophenyi)-N-[tcis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]-
2-furamide 553 (M + H)
1065 5-chloro-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)methyI]thiophene-2-
carboxamide 448 (M + H)
1066 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyC1-5hexyl)methyll-2,3-diphenylpropanamide 512 (M + H) J
1067 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methy!l-3-(2-hydroxyphenyI)propanamide 452 (M + H)
1068 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyll-5-iodo-2-furamide 524 (M + H) 3
1069 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino)cyclohexy])methyll-2-(2-iodopheny!)acetamide 548 (M + H) 3
1070 (2E)-N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-
2-yl]amino}cyclohexyl)methyl]-3-(3-nitrophenyl)acrvIamide 479 (M + H) 2
1071 N-[(cis-4- {[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyl)methyI]-3-oxoindane-l-carboxamide 462 (M + H) 3
1072 2-benzyl-N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyI]benzamide 498 (M + H)
1073 2,2-bis(4-chIorophenyl)-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)methyl]acetamide 566 (M + H) J
1074 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]-5-(4-methyl-2-nitrophenyI)-
2-furamide 533 (M + H)
1075 N-[(cis-4-{[4-(dimethylamino)-5J6,7I8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methyI]-5-nitrothiophene-2-carboxamide 459 (M + H) -1
1076 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino)cyclohexyl)methy]]-3-methy]-4-nitrobenzamide 467 (M + H) ">
1077 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino)cyclohexyl)methyl]-3-methoxy-4-nitrobenzamide 483 (M + H) 1

420

Ex. No. compound name MS class
1078 l-benzyl-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)methyl]-lH-
indoIe-3-carboxamide 537 (M + H)
1079 2-cyclohex-l-en-l-yl-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyi]acetamide 426 (M + H)
1080 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]-4-(4-ethoxyphenyl)-2-(3-methyl-5-
oxo-l-phenyl-4,5-dihydro-lH-pyrazol-4-y])-4-oxobutanamide 680 (M + H)
1081 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyI]-2-[2-(trifluoromethoxy)phenyl]-
acetamide 506 (M + H)
1082 4-(benzyloxy)-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)methyI]-3,5-
dimethylbenzamide 542 (M + H) -»
1083 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methy!l-9H-xanthene-9-carboxamide 512 (M + H)
1084 2-(l-benzothien-3-yI)-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yIlamino}cyclohexyl)methyIlacetamide 478 (M + H) -1
1085 N2-{cis-4-[(2,6-dimethoxybenzyI)amino]cyclohexyl}-N4,N4-
dimethylquinoline-2,4-diamine 435 (M + H) 3
1086 N2-{cis-4-[(2-ethoxybenzyI)amino]cyclohexyl}-N4,N4-
dimethylquinoline-2,4-diamine 419 (M + H)
1087 N2-{cis-4-[(lH-indol-3-yImethyl)amino]cyclohexyl}-N4,N4-
dimethylquinoline-2,4-diamine 414 (M + H) 3
1088 N2-{cis-4-[(2,5-dimethoxybenzyI)amino]cyclohexyl}-N4,N4-
dimethylquinoline-2,4-diamine 435 (M + H) 3
1089 N2-(cis-4- {[(4-methoxy-1 -naphthyl)methy l]amino} cyclohexy 1)-
N4,N4-dimethvlquinoline-2,4-diamine 455 (M + H)
1090 N2-(cis-4- {[(5-methoxy-l H-indoI-3-yI)methyl]amino} -
cyclohexyl)-N4,N4-dimethylquinoline-2,4-diamine 444 (M + H)
1091 N2-(cis-4-{[(2-methoxy-l-naphthyl)methyl]amino}cyclohexyl)-
N4,N4-dimethylquinoIine-2,4-diamine 455 (M + H) 3
1092 4-bromo-2-{[(cis-4-{[4-(dimethyIamino)quinolin-2-
yllamino}cyclohexyl)amino]methyI}-6-methoxyphenol 499 (M + H) 3
1093 N2-(cis-4-{[(5-bromo-lH-mdoI-3-yl)methyl]amino}cyclohexyl)-
N4,N4-dimethylquinoIine-2,4-diamine 492 (M + H) *■>
1094 N2-{cis-4-[(2,4-dimethoxybenzyl)amino]cyclohexyl}-N4,N4-
dimethylquinoline-2,4-diamine 435 (M + H)
1095 N4,N4-dimethyl-N2-{cis-4-[(2,3?4-
trimethoxybenzyt)aminolcyclohexyl)quinoline-2,4-diamine 465 (M + H) 3
1096 4-{[(cis-4-{[4-(dimethy!amino)quinolin-2-
yl]amino}cyclohexyl)amino]rnethyl}-2,6-dimethoxyphenol 451 (M + H) 3
1097 N2-{cis-4-[(3-ethoxy-4-rnethoxybenz5/I)amino]cyC1-5hexyl}-
N4,N4-dimethyIquinoline-2,4-diamine 449 (M + H)
1098 N4,N4-dimethyl-N2-{cis-4-[({3-[4-(trifluoromethyl)phenyI]-lH-
pyrazol-4-yl}methyl)amino]cyclohexyI}quinoline-2,4-diamine 509 (M + H) 3
1099 N4,N4-dimethyl-N2-{cis-4-[(3,4,5-
trimethoxybenzyl)aminolcyctohexyl}quinoline-2,4-diamine 465 (M + H)

421

Ex. No. compound name MS class
1100 N4,N4-dimethyI-N2-{cis-4-
[(pentamethylbenzyl)amino]cyC1-5hexyl}quino!ine-2,4-diamine 445 (M + H) ■>
1101 N2-{cis-4-[(3,5-dimethoxybenzyl)amino]cyclohexyl}-N4,N4-
dimethylquinoline-2,4-diamine 435 (M + H)
1102 4-{[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)amino]methyl}-2-iodo-6-methoxyphenol 547 (M + H) 3
1103 4-{[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)amino]methyl}-2,6-dimethylpheno] 419 (M + H) -i
1104 N2-{cis-4-[(3-methoxybenzyl)amino]cyclohexyl}-N4,N4-
dimethyIquinoline-2,4-diamine 405 (M + H) 3
1105 N2-{cis-4-[(3-bromo-4-fluorobenzyl)amino]cyclohexyl}-N4,N4-
dimethylquinoline-2,4-diamine 471 (M + H)
1106 N4,N4-dimethyl-N2-{cis-4-[(3-
phenylbutyl)amino]cyc!ohexyl}quinoIine-2,4-diamine 417 (M + H) 3
1107 3-{[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
amino]methyl}-6-methyl-4H-chromen-4-one 457 (M + H) 3
1108 3-{[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
aminolmethyl}-6,8-dimethyl-4H-chromen-4-one 471 (M + H) 3
1109 N2-(cis-4- {[(2,5-dimethy 1-1 -pheny 1-1 H-pyrrol-3-
yl)methyl]amino}cyclohexyl)-N4,N4-dimethylqutnoline-
2,4-diamine 468 (M + H) 3
1110 N4,N4-dimethyl-N2-{cis-4-[(2-
phenylpropyi)aminolcyclohexy!}quinoline-2,4-diamine 403 (M + H)
1111 N2-(cis-4-{[(2E)-2-benzyIideneheptyl]amino}cyclohexyl)-N4,N4-
dimethyIquinoIine-2,4-diamine 471 (M + H) 3
1112 N2-(cis-4-{[(2E)-3-(2-methoxyphenyl)prop-2-en-l-
yl]amino}cyC1-5hexyl)-N4,N4-dimethylquinoline-2,4-diamine 431 (M + H)
1113 6-chloro-3-{[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino} cyclohexyl)am ino] methyl}-4H-chromen-4-one 477 (M + H)
1114 N2-[cis-4-({[5-(4-fluorophenyl)pyridin-3-yl]methyl}amino)-
cyC1-5hexyll-N4,N4-dimethylquinoline-2,4-diamine 470 (M + H)
1115 ethyl 4,6-dichIoro-3-{[(cis-4-{[4-(dimethylamino)quinolin-2-
yI]amino}cyc!ohexyl)amino]methyU-lH-indole-2-carboxylate 552 (M-H) 1
1116 methyl 2-[(5-{[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexy l)amino]methyl} imidazo[2,1 -b] [ 1,3]thiazol-
6-yl)thio]benzoate 587 (M + H)
1117 N2-[cis-4-({[3-(4-fluorophenyl)-lH-pyrazol-4-yl]methyl}amino)-
cyclohexyll-N4,N4-dimethyIquinoline-2,4-diamine 459 (M + H) 1
1118 N4,N4-dimethyl-N2-(cis-4-{[4-
(methylthio)benzyl|amino}cyclohexyi)quinoline-2,4-diamine 421 (M + H) 1
1119 N4,N4-dimethyI-N2-{cis-4-[(l-
naphthylmethyI)amino]cyclohexyl}quinoline-2,4-diamine 425 (M + H) 1
1120 4-{[(cis-4-{[4-{dimethylamino)quinolin-2-
yl]amino}cyclohexyl)amino]methyl}-2-methoxyphenol 421 (M + H) 1
1121 N2-{cis-4-[(3-chloro-4-fluorobenzyl)amino]cyclohexyl}-N4,N4-
dimethylquinoIine-2,4-diamine 427 (M + H) 3
1122 N2-(cis-4-{[(2,6-dimethoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethyIquinoIine-2,4-diamine 449 (M + H) 2

422

Ex. No. compound name MS class
1123 N2-(cis-4-{[(2-ethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylquinoline-2,4-diamine 433 (M + H) 2
1124 N2-(cis-4-{[(lH-indol-3-ylmethyl)amino]methyl}cyclohexyl)-
N4,N4-dimethylquinoIine-2.4-diamine 428 (M + H) 3
1125 N2-(cis-4-{[(2,5-dimethoxybenzyl)amino]methyl}cyclohexyI)-
N4,N4-dimethylquinoline-2,4-diamine 449 (M + H) -i
1126 N2-[cis-4-({[(4-methoxy-l-naphthyl)methyl]amino}methyl)-
cyclohexyll-N4,N4-dimethy!quinoline-2,4-diamine 469 (M + H) 2
1127 N2-[cis-4-({[t5-methoxy-lH-indol-3-yl)methyl]amino}-
methyl)cyclohexyI]-N4,N4-dimethylquinoIine-2,4-diamine 458 (M + H) 3
1128 N2-[cis-4-( {[(2-methoxy-1 -naphthyl)methy l]amino} methyl)-
cyclohexyll-N4,N4-dimethylquinoline-2,4-diaraine 469 (M + H)
1129 4-bromo-2-({[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyl]amino}methyl)-6-methoxyphenol 513 (M + H) 2
1130 N2-[cis-4-({[(5-bromo-lH-indol-3-yl)methyl]amino}methyI)-
cyclohexyll-N4,N4-dimethylquinoline-2,4-diamine 506 (M + H) 2
1131 N2-(cis-4-{[(2,4-dimethoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethylquinoline-2,4-diamine 449 (M + H) 3
1132 N4,N4-dimethyl-N2-(cis-4-{[(2,3,4-trimethoxybenzyl)amino]-
methyl}cyclohexyI)-quinoline-2,4-diamine 479 (M + H)
1133 4-( {[(cis-4- {[4-(dimethyIamino)quinolin-2-y l]amino} cyclohexy 1)-
methyllamino}methvI)-2,6-dirnethoxyphenol 465 (M + H) 3
1134 N2-(cis-4-{[(3-ethoxy-4-methoxybenzyl)amino]methyl}-
cyC1-5hexvl)-N4,N4-dimethylquinoline-2,4-dianrine 463 (M + H)
1135 N4,N4-dimethyl-N2-(cis-4-{[({3-[4-(trifluoromethyl)phenyl]~lH-
pyrazol-4-yl} methy l)ami no] methyl} cyclohexyl)-quinoline-
2,4-diamine 523 (M + H)
1136 N45N4-dimethyl-N2-(cis-4-{[(3,4,5-trimethoxybenzyl)amino]-
methyl}cyclohexyl)-quinoIine-2,4-diamine 479 (M + H) 3
1137 N4,N4-dimethyl-N2-(cis-4-{[(pentamethylbenzyl)amino]-
methyl}cyclohexyl)-quinoline-2,4-diamine 459 (M + H) 3
1138 N2-(cis-4-{[(3,5-dimethoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethylquinoline-2,4-diamine 449 (M + H)
1139 4-{ {[(cis-4- {[4-(dimethylamino)quinolin-2-y l]amino} cyclohexy 1)-
methynamino)methyl)-2-iodo-6-methoxyphenol 561 (M + H) 3
1140 4-({[(cis-4-{[4-(dimethylamino)quinolin-2-
ynamino}cyclohexyl)methynamino)methyI)-2.6-dimethyIphenol 433 (M + H)
1141 N2-(cis-4-{[(4-methoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethylquinoline-2,4-diamine 419 (M + H)
1142 N2-(cis-4- {[(2,3-dihydro-1,4-benzodioxin-6-y Imethy l)amino]-
methyl}cyclohexyl)-N4,N4-dimethylquinoline-2,4-diamine 447 (M + H) 3
1143 N2-(cis-4-{[(3-bromobenzyI)amino]methyl}cyclohexyl)-N4,N4-
dimethylquinotine-2,4-diamine 467 (M + H)
1144 N2-(cis-4-{[(5-bromo-2,4-dimethoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethylquinoline-2,4-diamine 527 (M + H) 2
1145 N2-(cis-4-{[(5-bromo-2-methoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethylquinoline-2,4-diamine 497 (M + H) 3

423

Ex. No. compound name MS class
1146 3-chloro-4-({[(cis-4-{[4-(dimethylamino)quinolin-2-
vllamino)cyclohexyl)methyl]amino}methyl)phenol 439 (M + H)
1147 2-( {[(cis-4- {[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyllamino)methvl)benzonitrile 414 (M + H) 3
1148 N2-(cis-4-{[(3-chlorobenzyI)amino]methyl}cyclohexyl)-N4,N4-
dimethylquinoline-2,4-diamine 423 (M + H) ?
1149 N2-(cis-4-{[(4-chlorobenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylquinoline-2,4-diamine 423 (M + H)
1150 N2-[cis-4-t{[4-(diethylamino)benzyI]amino}methyl)cyclohexyl]-
N4,N4-dimethylquinoIine-2,4-diamine 460 (M + H) J
1151 N2-[cis-4-({[4-(dimethylamino)benzyl]amino}methyl)-
cyclohexyl]~N4,N4-dimethylquinoline-2,4-diamine 432 (M + H)
1152 N2-[cis-4-({[(9-ethyl-9H-carbazol-3-yl)methyl]amino}methyl)-
cyC1-5hexyl]-N4,N4-dimethylquinoline-2,4-diamine 506 (M + H) ->
1153 N2-[cis-4-({[2-fluoro-5-(trifluoromethyl)benzyl]amino}methyl)-
cyC1-5hexyl]-N4,N4-dimethylquinoline-2,4-diamine 475 (M + H) ->
1154 4-( {[(cis-4-{ [4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyllamino}methyl)phenol 405 (M + H)
1155 [5-( {[(cis-4- {[4-(dimethy lamino)quinolin-2-
yllamino}cyC1-5hexyl)methyl]amino}methyl)-2-furyllmethanol 409 (M + H)
1156 N2-(cis-4-{[(4-isopropoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethylquinoline-2,4-diamine 447 (M + H) 3
1157 N2-[cis-4-({[(5-ethyl-2-thienyl)methyl]amino}methyl)-
cyclohexyl]-N4,N4-dimethylquinoline-2,4-diamine 423 (M + H)
1158 N2-(cis-4-{[(3,3-diphenylprop-2-en-l-yl)amino]methyl}-
cvclohexyl)-N4,N4-dimethylquinoline-2,4-diamine 491 (M + H) 1
1159 4-( {[(cis-4- {[4-(dimethylamino)quinolin-2-
yIlamino}cyclohexyI)methyIlamino}methyl)-2-ethoxyphenol 449 (M + H) 3
1160 N2-{cis-4-[({[4-(dimethylamino)-l-naphthyl]methyl}amino)-
methyl]cyC1-5hexyI)-N4,N4-dimethylquinoline-2,4-diamine 482 (M + H) 3
1161 N4,N4-dimethyI-N2-(cis-4-{[(2,4,6-trimethoxybenzyl)-
amino]methyl)cyclohexyl)quinoline-2,4-diamine 479 (M + H) 2
1162 2-bromo-4-chloro-6-( {[(cis-4- {[4-(dimethylamino)quinolin-2-
yllamino} cyclohexyl)methyllamino) methy l)phenol 517 (M + H) 3
1163 3-({[(cis-4-{[4-(dimethyIamino)quinolin-2-
yl]aminojcyclohexyl)methyllamino}methyl)benzonitrile 414 (M + H) 3
1164 N2-(cis-4-{[(2-fluoro-5-methoxybenzyl)araino]methyl}-
cyclohexyl)-N4,N4-dimethyiquinoline-2,4-diamine 437 (M + H) 3
1165 N4,N4-dimethyl-N2-{cis-4-[({2-[(trifluoromethyl)thio]benzyl}-
amino)methyl]cyclohexyl}quinoline-2,4-diamine 489 (M + H) 3
1166 N2-(cis-4-{[(5-bromo-2-ethoxybenzyl)amino]methyl}-
cyclohexyI)-N4,N4-dimethylquinoline-2,4-diamine 511 (M + H) -■>
1167 N2-(cis-4-{[(2,4-dimethoxy-3-methylbenzyl)amino]methyl}-
cyC1-5hexyl)-N4,N4-dimethylquinoline-2,4-diamine 463 (M + H)
1168 N4,N4-dimethyI-N2-[cis-4-( {[2-(trifluoromethoxy)benzyl]-
amino}methyl)cyclohexyl]-quinoline-2,4-diamine 473 (M + H) 3
1169 N2-(cis-4- {[(2,5-diethoxybenzyl)amino]methy 1} cyclohexy 1)-
N4,N4-dimethylquinoIine-2,4-diamine 477 (M + H) 2

424

Ex. No. compound name MS class
1170 N2-(cis-4-{[(2,4-diethoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethylquinoline-2,4-diamine 477 (M + H) 2
1171 N2-(cis-4-{[(3,5-dibromo-2-methoxybenzyI)amino]methyl}-
cyclohexyl)-N4,N4-dimethylquinoline-2,4-diamine 575 (M + H) 2
1172 N2-[cis-4-({[2-(difluoromethoxy)benzyl]amino}methyl)-
cyclohexyI]-N4,N4-diniethylquinoline-2,4-diamine 455 (M + H) ■>
1173 N2-(cis-4-{[(5-fiuoro-2-methoxybenzyl)amino]methyi}-
cyclohexyl)-N4,N4-dimethyIquino!ine-2,4-diamine 437 (M + H) •>
1174 N4,N4-dimethyl-N2-(cis-4- {[(2,4,5-
triethoxyben2yI)aminolmethyl}cyclohexyl)quinoline-2,4-diamine 521 (M + H) 2
1175 N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-trimethoxybenzyl)amino]-
methyl}cyC1-5hexyI)-quinoline-2,4-diamine 479 (M + H) 2
1176 N2-(cis-4-{[(2;3-dimethoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethylquinoline-2,4-diamine 449 (M + H) -*
1177 N2-[cis-4-({[2-(allyloxy)benzyl]amino}methyl)cyC1-5hexyl]-
N4,N4-dimethylquinoline-2,4-diamine 445 (M + H) 2
1178 N2-(cis-4- {[(1 -benzothien-3-ylmethy l)amino]methyl} -
cyclohexyl)-N4,N4-dimethylquinoline-2,4-diamine 445 (M + H) 3
1179 N4,N4-dimethyl-N2-[cis-4-({[(l-methyl-lH-indol-3-
yl)methyllamino}methyl)cyclohexyl]quinoline-2,4-diamine 442 (M + H) 3
1180 N4,N4-dimethyl-N2-[cis-4-({[(5-methyI-2-
thienyl)methyllamino}methyl)cyclohexyl]quinoline-2,4-diamine 409 (M + H) 3
1181 N2-(cis-4-{[(mesitylmethyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylquinoline-2,4-diamine 431 (M + H) 3
1182 N2-(cis-4- {[(1,3-benzodioxol-5-y lmethyl)amino] methyl} -
cyclohexyl)-N4,N4-dimethylquinoIine-2,4-diamine 433 (M + H)
1183 N4,N4-dimethyl-N2-(cis-4- {[(3-
thienylmethyl)aminolmethyl}cyclohexyI)quinoline-2,4-diamine 395 (M + H) 3
1184 N4,N4-dimethyl-N2-(cis-4-{[(3-
methylbenzyl)aminolmethyI}cvclohexyl)quinoline-2,4-diamine 403 (M + H) 3
1185 N4,N4-dimethy l-N2-(cis-4- {[(2-
methyIbenzyl)amino]methyl}cyclohexyl)quinoline-2,4-diamine 403 (M + H) 3
1186 N4,N4-dimethyI-N2-(cis-4-{ [(4-
methylbenzyl)aminol methyl} cyclohexyl)quinoline-2,4-diamine 403 (M + H) 3
1187 N2-(cis-4-{[(3,5-dichlorobenzyI)amino]methyI}cyclohexyI)-
N4,N4-dimethyIquinoline-2,4-diamine 457 (M + H) 3
1188 N2-[cis-4-({[(7-methoxy-l,3-benzodioxol-5-yl)methyl]amino}-
methyl)cyclohexyl]-N4,N4-dimethylquinoline-2,4-diamine 463 (M + H) 2
1189 N2-(cis-4-{[(3-bromo-4,5-dimethoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethylquinoline-2,4-diamine 527 (M + H) 3
1190 N2-(cis-4-{[(4-methoxy-3-methylbenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethy!quinoIine-2,4-diamine 433 (M + H) 3
1191 N2-(cis-4-{[(2-bromo-4,5-dimethoxybenzyi)amino]methyl}-
cyclohexyl)-N4,N4-dimethy!quinoline-2,4-diamine 527 (M + H) 3
1192 N4,N4-dimethyl-N2-[cis-4-({[(2-methyl-5-phenyl-3-
furyl)methyllamino}methyl)cyC1-5hexynquinoline-2,4-diamine 469 (M + H) 3
1193 N2-(cis-4-{[(3,4-dimethoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethylquinoline-2,4-diamine 449 (M + H) ■>

425

Ex. No. compound name MS class
1194 4-({[(cis-4-{[4-(dimethyfamino)quinolin-2-
yl]amino}cyC1-5hexyl)methyl]amino}methyI)-2-methylphenol 419 (M + H) ->
1195 N2-(cis-4-{[(4-methoxy-2,5-dimethylben2yI)amino]methyI}-
cyclohexyl)-N4,N4-dimethylquinoIine-2,4-diamine 447 (M + H) "i
1196 2-({[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyl]amino}methyl)-6-methoxyphenol 435 (M + H)
1197 N2-[cis-4-({[3-chloro-2-fluoro-5-(trifluoromethyl)benzyl]-
amino}methyl)cyclohexyI]-N4,N4-dimethylquinoline-2,4-dianiine 509 (M + H) 3
1198 N2-[cis-4-({[3-fluoro-5-(trifluoromethyl)benzyi]amino}-
methyl)cyC1-5hexyIl-N4,N4-dimethyIquinoline-2,4-diamine 475 (M + H) 3
1199 4-({[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
methyl]amino}methy])-2-fluoro-6-methoxyphenoI 453 (M + H)
1200 N2-(ds-4-{[(2-fluoro-4,5-dimethoxybenzyl)amino]methyl}-
cyclohexyl)-N4JV4-dimethylquinoIine-2,4-diamine 467 (M + H)
1201 N2-(cis-4- {[(2-ethy Ibenzyl)amino]methyl} cyclohexyl)-N45N4-
dimethylquinoIine-2,4-diamine 417 (M + H) 3
1202 3-[[4-({[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)methyl]amino}methyl)phenyl](methyl)amino]-
propanenitrile 471 (M + H) 3
1203 N2-{cis-4-[({4-[(4-bromobenzyl)oxy]benzyl}amino)methyl]-
cyclohexyl}-N4,N4-dimethylquinoline-2,4-diamine 573 (M + H) -i
1204 N2-(cis-4-{[(3,5-dibromo-2-ethoxybenzyI)amino]methyl}-
cyC1-5hexyl)-N4,N4-dimethylquinoIine-2,4-diamine 589 (M + H) 3
1205 N2-{cis-4-[(2,6-dimethoxybenzyI)amino]cyclohexyl}-N4,N4-
dimethylpyrirnidine-2,4-diamine 386 (M + H) 3
1206 N2-{cis-4-[(2-ethoxybenzyI)amino]cyC1-5hexyl}-N4,N4-
dimethylpyrimidine-2,4-diamine 370 (M + H) ->
1207 N2-{cis-4-[(lH-indol-3-ylmethyl)amino]cyclohexyl}-N4,N4-
dimethy!pyrimidine-2,4-diamine 365 (M + H) 3
1208 N2-{cis-4-[(2,5-dimethoxybenzyl)amino]cyclohexyl}-N4,N4-
dimethylpyrimidine-2,4-diamine 386 (M + H) 3
1209 N2-(cis-4-{[(4-methoxy-l-naphthyl)methyI]amino}cyclohexyl)-
N4JsJ4-dimethylpyrimidine-2,4-diamine 406 (M + H) 3
1210 N2-(cis-4-{[(5-methoxy-lH-indol-3-yl)methyl]amino}-
cyC1-5hexvi)-N4,N4-dimethyIpyrimidine-2,4-diamine 395 (M + H) 3
1211 N2-(cis-4- {[(2-methoxy-1 -naphthyl)methyl]amino} cyclohexy 1)-
N4,N4-dimethylpyrimidine-2,4-diamine 406 (M + H)
1212 4-bromo-2- {[(cis-4-{ [4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)amino]methyl}-6-methoxyphenoI 450 (M + H) 3
1213 N2-(cis-4-{[(5-bromo-lH-indol-3-yl)methyl]amino}cyclohexyl)-
N4,N4-dimethyIpyrimidine-2,4-diamine 443 (M + H) 2
1214 N2-{cis-4-[(2,4-dimethoxybenzyI)amino]cyclohexyl}-N4,N4-
dimethyIpyrimidine-2,4-diamine 386 (M+H)
1215 N4,N4-dimethyl-N2-{cis-4-[(2,3,4-
trimethoxybenzvI)amino]cyclohexyl}pyrimidine-2,4-diamine 416 (M + H)
1216 4-{[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino} eye lohexyl)ami no] methyl} -2,6-dimethoxyphenol 402 (M + H) 3

426

Ex. No. compound name MS class
1217 N2-{cis-4-[(3-ethoxy-4-methoxybenzyl)amino]cyclohexyl}-
N4,N4-dimethyIpyrimidine-2,4-diamine 400 (M + H)
1218 N4,N4-dimethyl-N2-{cis-4-[({3-[4-(trifluoromethyl)phenyl]-lH-
pyrazo!-4-yl}methyl)amino]cyclohexyl)pyrimidine-2,4-diamine 460(M-HH) 3
1219 N4,N4-dimethyl-N2-{cis-4-[(3,4,5-
trimethoxybenzyl)amino]cyclohexyl}pyrimidine-2,4-diamine 416 (M + H) 3
1220 N4,N4-dimethyl-N2-{cis-4-
ffpentamethylbenzyl)amino]cyclohexyl}pyrimidine-2,4-diamine 396 (M + H) -t
J
1221 N2-{cis-4-[(3,5-dimethoxybenzyl)amino]cyC1-5hexyl}-N4,N4-
dimethylpyrimidine~2,4-diamine 386 (M + H) *■»
1222 4-{[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)aminolmethyl}-2-iodo-6-methoxyphenol 498 (M + H)
1223 4-{ [(cis-4- {[4-(dimethy lamino)pyrimidin-2-
yljamino} cycl oh exyl)aminq]m ethyl} -2,6-dimethylphenol 370 (M + H)
1224 N2-{ds-4-[(3-methoxybenzy[)amino]cyC1-5hexyl}-N4,N4-
dimethyIpyrimidine-2,4-diamine 356 (M + H)
1225 N2-{cis-4-[(3-bromo-4-fluorobenzy!)amino]cyclohexy!}-N4,N4-
dimethylpyrimidine-2,4-diamine 422 (M + H) ^>
1226 N4,N4-dimethyl-N2-{cis-4-[(3-
phenylbutyl)amino]cyclohexyl}pyrimidine-2,4-diamine 368 (M + H) j
1227 3- {[(cis-4- {[4-(dimethy lamino)pyrimidin-2-y l]amino} -
cyclohexyl)-amino]methyl}-6-methyl-4H-chromen-4-one 408 (M + H) 3
1228 6-chtoro-3'{[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}-
cyclohexyl)amino]methyl)-7-methyl-4H-chromen-4-one 442 (M + H)
1229 3-{[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}-
cyclohexyl)-amino1methyl}-6,8-dimethyl-4H-chromen-4-one 422 (M + H) J
1230 N2-(cis-4"{[(2,5-dimethyl-l-phenyl-lH-pyrrol-3-yl)methyl]-
amino}cyclohexyl)-N4,N4-dimethylpyrimidine-2,4-diamine 419 (M + H) 3
1231 N4,N4-dimethyI-N2-{cis-4-[(2-
phenylpropvl)amino]cyclohexvl}pyrimidine-2,4-diamine 354 (M + H) 3
1232 N2-(cis-4-{[(2E)-2-benzylideneheptyl]amino}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine 422 (M + H) 3
1233 N2-(cis-4-{[(2E)-3-(2-methoxyphenyl)prop-2-en-l-
yl]amino}cyclohexyl)'N4,N4-dtmethylpyrimidine-2,4-diamine 382 (M + H)
1234 6-chIoro-3-{[(cis-4-{[4-(dimethy!amino)pyrimidin-2-
yl]arnino}cyclohexyl)amino]methyl}-4H-chromen-4-one 428 (M + H)
1235 N2-[cis-4-({[5-(4-fluorophenyI)pyridm-3-yf]methyl}-
amino)cyclohexyI]-N4,N4-dimethyIpyrimidine-2,4-diamine 421 (M + H) 2
1236 ethyl 4,6-dichloro-3-{[(ciS'4-{[4'(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)aminolinethyI}-lH-indo]e-2-carboxylate 503 (M-H) 1
1237 methyl 2'[(5-{[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl]ammo}cyclohexyl)amino]methyl}imida2o[2,l-b][l,3]thiazol-
6--yl)thio]benzoate 538 (M + H) ->
1238 N2-[cis-4-( {[3-(4-fluorophenyl> 1 H-pyrazoI-4-yl] methyl} -
amino)cyclohexyl]-N4,N4-dimethylpyrimidine-2,4-diamine 410(M + H)
1239 N4,N4-dimethyl-N2-(cis-4-{[4-
(methyithio)benzyl]amino}cyclohexyl)pyrimidine-2,4-diamine 372 (M + H) 3

427

Ex. No. compound name MS class
1240 N4,N4-dimethyl-N2-{cis-4-[(l-
naphthylmethyl)ammo]cyclohexyl}pyrimidtne-2,4-diamine 376 (M + H) ■I
1241 4-{[(cis-4-{[4-(dimethy!amino)pyrimidin-2-
yIlamino}cyclohexyl)amino]methyl}-2-methoxyphenol 372 (M + H) ">
1242 N2-{ciS'4-[(3-chloro-4-fluorobenzyl)amino]cyclohexyl}-N4,N4-
dimethylpyrimidine-2,4-diamine 378 (M + H) 3
1243 N2-(cis-4-{[(2,6~dimethoxybenzyl)amino]methyl}cyC1-5hexyl)-
N4,N4-dimethylpyrimidine-2,4-diamtne 400 (M + H) 2
1244 N2-(cis-4-{[(2-ethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine 384 (M + H) 2
1245 N2-(cis-4-{[(IH-mdol-3-ylmethyl)amino]methyl}cyclohexyl)-
N4,N4-dimethylpyrimidine-2,4-diamine 379 (M + H) 3
1246 N2-(cis-4-{[(2,5-dimethoxybenzyl)amino]methyl}cyclohexyl)-
N4>N4'dtmethylpyrimidine-2,4-diamine 400 (M + H) 3
1247 N2-[cis-4-({[(4-methoxy-l-naphthyl)methyl]amino}methyl)-
cyclohexyl]-N4,N4-dimethylpyrimidine-2,4-diamine 420 (M + H) I
1248 N2-[cis-4-({[(5-methoxy-lH-indolo-yl)methyl]amino}-
methyl)cyclohexytl-N41N4-dimethylpyrimidine-2,4-diamine 407 (M - H) 2
1249 N2-[cis-4-({[(2-methoxy-l-naphthy!)methyl]amino}methyl)-
cyC1-5hexyl]-N4,N4-dimethylpyrimidine-2,4-diamine 420 (M + H) 1
1250 4-bromo-2-({[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl]amino)cydohexyl)methyl]ammo}methyl)-6-methoxyphenol 462 (M - H) 1
1251 N2-fcis-4-({[(5-bromo-lH-indol-3-yI)methyl]amino}methyI)-
cyclohexyl]-N4,N4-dimetbvlpyrimidine-2,4-diamine 455 (M-H) 1
1252 N2-(cis-4-{[(2,4-dimethoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethyIpyrimidine-2,4-diamine 400 (M + H) 2
1253 N4,N4-dimethyUN2-(cis-4-{[(2,3,4-trimethoxybenzyl>
amino1methyl}cyclohexyl)-pyrimidine-2,4-diamine 430 (M + H) 1
1254 4-({[(cis-4-{[4-(dimethylammo)pyrimidin-2'yl]amino}-
cyC1-5hexyl)methyI]amino)methyI)-2,6-dimethoxyphenol 414 (M-H)
1255 N2-(cis-4-{[(3-ethoxy-4-methoxybenzyI)amino]methy!}-
cyclohexyl)-N4,N4-dimethvlpyrimidine-2,4-diamine 414 (M + H) 1
1256 N4,N4-dimethyl-N2-(cis-4-{[({3-[4'(trifluoromethyl)phenyl]-lH-
pyrazo!'4-yl}methyl)amtno]methyl}cyclohexyl)-
pyrimidine-2,4-diamine 474 (M + H) 1
1257 N45N4-dimetbyl-N2-(cis-4-{[(3?4;54rimethoxybenzyl)-
amino]methyl}cyclohexyl)-pyrimidine-2,4-diamine 430 (M + H) 2
1258 N4,N4-dimethy I-N2-(cis-4- {[(pentamethy! benzyl >
amino]methyi}cyclohexyl)-pyrimidine-2,4-diamine 410 (M + H) 3
1259 N2-(cis-4-{[(3,5-dimethoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethyIpyrimidine-2,4-diamine 400 (M + H) 3
1260 4-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexYl)niethyl]amino}methyl)-2-iodo-6-methoxyphenol 512(M + H) 1
1261 4-( {[(cis-4-{ [4-(dimethylamino)pyrimidin-2'
yl]amino}cyc!ohexyl)methyl]amino}methyl)-2,6-dimethylphenol 382 (M - H) 1
1262 N2~(cis-4- {[(4-methoxybenzy l)amino]methy 1} cyclohexy 1)-
N4,N4-dimethylpyrimidine-2,4-diamine 370 (M + H) 3

428

Ex. No. compound name MS class
1263 N2-(cis-4-{[(2,3-dihydro-l,4-benzodioxin-6-yImethyl)amino]-
methvUcyclohexyl)-N4,N4-dimethvIpvrimidine-2,4-diamine 398 (M + H)
1264 N2-(cis-4-{[(3-bromobenzyI)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine 418 (M + H) ">
1265 N2-(cis-4-{[(5-bromo-2,4-dimethoxybenzyl)amino]methyl}-
cyC1-5hexyI)-N4,N4-dimethylpyriraidine-2,4-diamine 478 (M + H) 1
1266 N2-{cis-4-{[(5-bromo-2-methoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethylpyrimidine-2,4-diamine 448 (M + H) 1
1267 3-chloro-4-( {[(cis-4- {[4-(dimethyIamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]amino}methyi)phenol 388 (M-H) ■>
1268 2-({[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
ynamino}cyclohexyl)methyl]amino}methyl)benzonitrile 365 (M + H)
1269 N2-(cis-4-{ [(3-chlorobenzyl)amino] methyl} cyC1-5hexyl)-N4 ,N4-
dimethylpyrimidine-2,4-diamine 374 (M + H) 3
1270 N2-(cis-4-{[(4-chlorobenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine 374 (M + H) 3
1271 N2-[cis-4-({[4-(diethylamino)benzyl]amino}methyl)cyclohexyI]-
N4,N4-dimethylpyrimidine-2,4-diamine 411 (M + H) 2
1272 N2-[cis-4-({[4-(dimethyIamino)benzyl]amino}methyl)-
cyclohexyl]-N4.N4-dimethylpyrimidine-2,4-diamine 383 (M + H) 3
1273 N2-[cis-4-( {[(9-ethy l-9H-carbazol-3-yl)methyl]amino} -
methyl)cyC1-5hexyll-N4,N4-dimethylpyrimidine-2,4-diamine 457 (M + H) 1
1274 N2-[cis-4-({[2-fluoro-5-(trifIuoromethyI)benzyl]amino}-
methyl)cyclohexyll-N4,N4-dimethylpyrimidine-2,4-diamine 426 (M + H) -i
1275 4-( {[(cis-4- {[4-(dimethy!amino)pyrimidin-2-
yl]amino}cyclohexyl)methyllamino}methyl)phenol 354 (M-H)
1276 [5-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yIlamino}cyclohexyl)methyllamino}methyI)-2-furyllmethanol 360 (M + H) 1
1277 N2-(cis-4-{[(4-isopropoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethvlpyrimidine-2,4-diamine 398 (M + H) 2
1278 N2-[cis-4-({[(5-ethyl-2-thienyl)methyl]amino}methyl)-
cyclohexvl]-N4,N4-dimethylpyrimidine-2,4-diamine 374 (M + H)
1279 N2-(cis-4-{[(3,3-diphenylprop-2-en-l-yI)amino]methyl}-
cyclohexyl)-N4,N4-dimethylpyrimidine-2,4-diamine 442 (M + H) 1
1280 4-({[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl]amino}cyclohexyl)methyI]amino}methyl)-2-ethoxyphenol 400 (M + H) 2
1281 N2-{cis-4-[( {[4-(dimethy lamino)-1 -naphthyl]methy 1} amino)-
methyI]cyC1-5hexyI}-N4,N4-dimethylpyrimidine-2,4-diamine 433 (M + H) 2
1282 N4,N4-dimethyl-N2-(cis-4-{[(2,4,6-trimethoxybenzyl>
aminolmethyHcyclohexyI)-pyrimidine-2,4-diamine 430 (M + H) 1
1283 2-bromo-4-chloro-6-( {[(cis-4- {[4-(dimethylamino)pyrimidin-2-
y!lamino}cyclohexyl)methyl"|amino)methyl)pheno! 468 (M + H) 3
1284 3-( {[(cis-4- {[4-(dtmethyiamino)pyrimidin-2-
yllamino}cyclohexyl)methyl]amino}methyl)benzonitrile 365 (M + H) 3
1285 N2-(cis-4-{[(2-fluoro-5-methoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethylpyrimidine-2,4-diamine 388 (M + H) ■^
j
1286 N4,N4-dimethyl-N2-{cis-4-[({2-[(trifluoromethyl)thio]benzyl}-
amino)methyl]cyclohexyI}pyrimidine-2,4-diamine 440 (M + H)

429

Ex. No. compound name MS class
1287 N2-(cis-4-{[(5-bromo-2-ethoxybenzyl)amino]methyl}-
cyC1-5hexvl)-N4,N4-dimethylpvrimidine-2,4-diamine 462 (M + H) 1
1288 N2-(cis-4-{[(2,4-dimethoxy-3-methylbenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethyIpyrimidine-2,4-diamine 414 (M + H) 1
1289 N4,N4-dimethyl-N2-[cis-4-({[2-(trifiuoromethoxy)benzyl]-
amino}methyl)cyclohexyI]pyrimidine-2,4-diamine 424 (M + H) ->
1290 N2-(cis-4-{[(2,5-diethoxybenzyl)amino]methyl}cyclohexyI)-
N4,N4-dimethylpyrimidine-2,4-diamine 428 (M + H) 1
1291 N2-(cis-4-{[(2,4-diethoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethylpyrimidine-2,4-diamine 428 (M + H) 2
1292 N2-(cis-4-{[(3,5-dibromo-2-methoxybenzyI)amino]methyl}-
cyC1-5hexyl)-N4,N4-dimethy]pyrimidine-2,4-diamine 526 (M + H) 1
1293 N2-[cis-4-({[2-(difluoromethoxy)benzyl]amino}methyl)~
cyclohexvll-N4,N4-dimethylpyrimidine-2,4-diamine 406 (M + H)
1294 N2-(cis-4-{[(5-fluoro-2-methoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethylpyrimidine-2,4-diamine 388 (M + H)
1295 N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-triethoxybenzyl)-
aminolmethyl}cvC1-5hexyI)-pyrimidine-2,4-diamine 472 (M + H) 1
1296 N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-trimethoxybenzyl)-
amino]methyl}cyclohexyl)-pyrimidine-2,4-diamine 430 (M + H) 2
1297 N2-(cis-4- {[(2,3-dimethoxybenzyl)amino]methyl} cyclohexyl)-
N4,N4-dimethy]pyrimidine-2,4-diamine 400 (M + H) 3
1298 N2-[cis-4-( {[2-(allyloxy)benzyl]amino} methyl)cyclohexy 1]-
N4,N4-dimethylpyrimidine-2,4-diamine 396 (M + H) 1
1299 N2-(cis-4- {[(1 -benzothien-3-yImethyl)amino] methyl} -
cyclohexyl)-N4,N4-dimethylpyrimidine-2,4-diamine 396 (M + H) 3
1300 N4,N4-dimethyl-N2-[cis-4-({[(l-methyl-lH-indol-3-
yi)methyllamino}methyl)cyclohexyllpyrimidine-2,4-diamine 393 (M + H) 2
1301 N4,N4-dimethyl-N2-[cis-4-({[(5-methyl-2-
thienyl)methyilamino}methyl)cyC1-5hexyllpyrimidine-2,4-diamine 360 (M + H)
1302 N2-(cis-4-{[(mesitylmethyI)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine 382 (M + H) -i
1303 N2-(cis-4-{[(l,3-benzodioxol-5-ylmethyl)amino]methyl}-
cyclohexyI)-N4,N4-dtmethyIpyrimidine-2,4-diamine 384 (M + H) ->
1304 N4,N4-dimethyl-N2-(cis-4- {[(3-
thienylmethyI)aminolraethvl}cyclohexyl)pyrimidine-2,4-diamine 346 (M + H) 3
1305 N4,N4-dimethyl-N2-(cis-4-{[(3-
methylbenzyl)aminolmethyl}cyclohexyl)pyrimidine-2,4-diamine 354 (M + H) 3
1306 N4,N4-dimethyl-N2-(cis-4-{[(2-
methylbenzvl)aminolmethyl}cyclohexyI)pyrimidine-2,4-diamine 354 (M + H) 3
1307 N4,N4-dimethyI-N2-(cis-4-{[(4-
methylbenzyl)amino]methyl}cyclohexyl)pyrimidine-2,4-diamine 354 (M + H) 3
1308 N2-(cis~4-{[(3,5-dichloroben2yl)amino]methyI}cyclohexyl)-
N4,N4-dimethyIpyrimidine-2,4-diamine 408 (M + H) 3
1309 N2-[cis-4-({[(7-methoxy-l,3-benzodioxol-5-yl)methyl]amino}-
methyl)cyclohexyl]-N4,N4-dimethyIpyrimidine-2,4-diamine 414 (M + H) 1
1310 N2-(cis-4- {[(3-bromo-4,5-dimethoxybenzyl)amino]methyl }-
cyclohexyl)-N4,N4-dimethylpyrimidine-2,4-diamine 478 (M + H) 1

430

Ex. No. compound name MS class
1311 N2-(cis-4-{[(4-methoxy-3-methylbenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethYlpyrimidine-2,4-diamine 384 (M + H) 2
1312 N2-(cis-4-{[(2-bromo-4,5-dimethoxybenzyl)amino]methyl}-
cyclohexyI)-N4,N4-dimethylpyrimidine-2,4-diamine 478 (M + H) 2
1313 N4,N4-dimethyl-N2-[cis-4-({[(2-methyl-5-phenyl-3-
furyl)methyl]amino}methyl)cyclohexynpyrimidine-2,4-diamine 420 (M + H)
1314 N2-(cis-4-{[(3,4-dimethoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethylpyrimidine-2,4-diamine 400 (M + H) 2
1315 4-( {[(cis-4- {[4-(dimethylamino)pyrimidin-2-
yl]amino}cyC1-5hexyl)methynamino}methyI)-2-methyIphenol 368 (M - H) 3
1316 N2-(cis-4- {[(4-methoxy-2,5-dimethylbenzyI)amino]methyI} -
cyclohexyI)-N4,N4-dimethylpyrimidine-2,4-diamine 398 (M + H) 2
1317 2-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexvl)methyIlamino}methyl)-6-methoxyphenoI 386 (M + H) 3
1318 N2-[cis-4-({[3-chloro-2-fluoro-5-(trifluoromethyl)benzyl]amino}-
methyl)cyC1-5hexyll-N4,N4-dimethylpvrimidine-2,4-diamine 460 (M + H) 3
1319 N2-[cis-4-({[3-fluoro-5-(trifluoromethyl)benzyl]amino}-
methyl)cyclohexvll-N4,N4-dimethylpyrimidine-2,4-diamine 426 (M + H)
1320 4-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)methyI]amino)methyl)-2-fluoro-6-methoxyphenol 402 (M - H)
1321 N2-(cis-4-{[(2-fluoro-4,5-dimethoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethylpyrimidine-2,4-diamine 418 (M + H)
1322 N2-(cis-4- {[(2-ethylbenzyI)amino]methyl} cyclohexyl)-N4,N4-
dimethyIpyrimidine-2,4-diamine 368 (M + H) 3
1323 3-[[4-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)-methyl]amino}methy])phenyl](methyl)aminoj-
propanenitrile 422 (M + H) 2
1324 N2-{cis-4-[({4-[(4-bromobenzyl)oxy]benzyl}amino)methyl]-
cyclohexyl}-N4,N4-dimethylpyrimidine-2,4-diamine 524 (M + H) 2
1325 N2-(cis-4-{[(3,5-dibromo-2-ethoxybenzyl)amino]methyl}-
cyclohexyI)-N4,N4-dimethyIpyrimidine-2,4-diamine 540 (M + H) 2
1326 N2-{cis-4-[(2,6-dimethoxybenzyI)amino]cyC1-5hexyl}-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 440 (M + H) 3
1327 N2-{cis-4-[(2-ethoxybenzyl)amino]cyclohexyI}-N4,N4-dimethyl-
5,6,7,8-tetrahydroquinazoIine-2,4-diamine 424 (M + H) 3
1328 N2-{cis-4-[(lH-indol-3-ylmethyI)amino]cyclohexyl}-N4;N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 419 (M + H) ">
1329 N2-{cis-4-[(2,5-dimethoxybenzyl)amino]cyclohexyl}-N4,N4-
d i methyl - 5,6,7,8 -tetrahydroqu i nazol in e-2,4-d i am i ne 440 (M + H) *>
j
1330 N2-(cis-4- {[(4-methoxy-1 -naphthyl)methyl]amino} cyclohexyl)-
N4,N4-dimethyl-5,6,7,8-tetrahvdroquinazoline-2,4-diamine 460 (M + H)
1331 N2-(cis-4- {[(5-methoxy-1 H-indol-3-yI)methyl]amino} -
cyclohexyl)-N4,N4-dimethyl-5,6,7r8-tetrahydroquinazoline-
2,4-diamine 449 (M + H) 1
1332 N2-(cis-4-{[(2-methoxy-l-naphthyI)methyl]amino}cyC1-5hexyl)-
N4,N4-dimethyI-5,6,7,8-tetrahydroquinazoIine-2,4-diamine 460 (M + H)

431

Ex. No. compound name MS class
1333 4-bromo-2-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyI)amino]methyl}-6-
methoxyphenol 504 (M + H) ->
1334 N2-(cis-4-{[(5-bromo-lH-indol-3-yl)methyl]amino}cyC1-5hexyl)-
N4,N4-dimethyl-5,6,7,8-tetrahydroquina2oline-2,4-diamine 497 (M + H) 3
1335 N2-{cis-4-[(2,4-dimethoxybenzyI)amino]cyclohexyl}-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 440 (M + H)
1336 N4,N4-dimethyl-N2-{cis-4-[(2,3,4-trimethoxybenzyl)amino]-
cyclohexvl}-5,6,7,8-tetrahydroquinazoline-2,4-diamine 470 (M + H) ->
1337 4-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)aminolmethyI}-2,6-dimethoxyphenol 456 (M + H) 2
1338 N2-{cis-4-[(3-ethoxy-4-methoxybenzyl)amino]cyclohexyl}-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 454 (M + H)
1339 N4,N4-dimethyl-N2-{cis'4-[({3-[4-(trifluoromethyI)phenyl]-lH-
pyrazol-4-yl}methyl)amino]cyclohexyl}-5,6,7,8-
tetrahvdroquinazoline-2,4-diamine 514 (M + H) "*
1340 N4,N4-dimethyl-N2-{ciS'4-[(3,4,5-trimethoxybenzyl)amino]-
cyclohexyl}-5,6,7,8-tetrahydroquinazoline-2,4-diamine 470 (M + H) ^>
1341 N4,N4-dimethyl-N2-{cis-4-[(pentamethylbenzyl)amino]-
cyclohexyl}-5,6,7,8-tetrahydroquinazo!ine-2,4-diamine 450 (M + H) 2
1342 N2-{cis-4-[(3,5-dimethoxybenzyl)amino]cyC1-5hexyl}-N4,N4-
dimethyI-5,6,7,8-tetrahydroquinazoline-2,4-diamine 440 (M + H) 2
1343 4-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)amino]methyl}-2-iodo-6-methoxyphenol 552 (M + H) 2
1344 4-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin'2-
yl]amino}cvC1-5hexyl)aminolinethyl}'2,6-dimethylphenol 424 (M + H) 3
1345 N2-{cis-4-[(3-methoxybenzyl)amino]cyclohexyl}-N4,N4-
dimethyl-5,6,7,8-tetrahvdroquinazoline-2,4-diamine 410 (M + H)
1346 N2-{cis-4-[(3-bromo-4-fluorobenzyl)amino]cyclohexyl}-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diaraine 476 (M + H)
1347 N4,N4-dimethyl-N2-{cis-4-[(3-phenylbutyl)amino]cyclohexyl}-
5,6,7,8-tetrahydroquinazoline-2,4-diamine 422 (M + H) 3
1348 3-{[(cis-4-{[4-(dimethylamino)-5,6,7J8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)amino]methyl}-6-methyl-
4H-chromen-4-one 462 (M + H) 3
1349 6-chIoro-3-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)amino]methyl}-
7-methyl-4H-chromen-4-one 496 (M + H) 3
1350 3-{[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)amino]methyl}-6,8-diraethyl-
4H-chromen-4-one 476 (M + H) 2
1351 N2-(cis-4-{[(2,5-dimethyl-l-phenyl-lH-pyrrol-3-
yI)methyl]amino}cyclohexyI)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine 473 (M + H)
1352 N4,N4-dimethyl-N2-{cis-4-[(2-phenyIpropyl)amino]cyclohexyl}-
5,6,7,8-tetrahydroquinazoline-2,4-diamine 408 (M + H) 3
1353 N2-(cis-4-{[(2E)-2-benzylideneheptyl]amino}cyclohexyl)-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 476 (M + H)

432

1 Ex. No. compound name MS class
1354 N2-(cis-4-{[(2E)-3-(2-methoxyphenyl)prop-2-en-l-
yl]amino}cyclohexyI)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine 436 (M + H)
1355 6-chIoro-3-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)amino]methyI}-4H-
chromen-4-one 482 (M + H) 1
1356 N2-[cis-4-({[5-(4-f]uorophenyl)pyridin-3-yl]methyl}-
amino)cyC1-5hexyI]-N4,N4-dimethyI-5,6,7,8-
tetrahydroquinazoline-2,4-diamine 475 (M + H)
1357 ethyl 4,6-dichloro-3-{[(cis-4'{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino} cyclohexyl)amino]methy 1} -1H-
indole-2-carboxylate 559 (M + H) 1
1358 methyl 2-[(5-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyI)amino]-
methvl}imidazo-[2,l-b][l,31thiazol-6-vl)thiolbenzoate 592 (M + H)
1359 N2-[cis-4-( {[3-(4-fluorophenyl)-l H-pyrazol-4-
yl]methyl}amino)cyclohexyI]-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoIine-2,4-diamine 464 (M + H) 1
1360 N4,N4-dimethyl-N2-(cis-4- {[4-(raethyIthio)benzy l]amino} -
cyclohexy!)-5,6,7,8-tetrahvdroquinazoline-2,4-diamine 426 (M + H) t
1361 N4,N4-dimethyl-N2-{cis-4-[(l-naphtbylmethyl)amino]-
cyclohexyI}-5,6,7,8-tetrahydroquinazoline-2,4-diamine 430 (M + H) 3
1362 4-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyI)amino]methyl}-2-methoxyphenol 426 (M + H) 3
1363 N2-{cis-4-[(3-chloro-4-fluorobenzyl)amino]cyclohexyl}-N4,N4-
dimethyI-5,6,7,8-tetrahydroquinazoline-2,4-diamine 432 (M + H) ^
1364 N2-(cis-4-{[(2,6-dimethoxybenzyl)amino]methyI}cyclohexyl)-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2.4-diamine 454 (M + H) 1
1365 N2-(cis-4- {[(2-ethoxybenzy l)amino]methyl} cyclohexyl)-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 438 (M + H) 2
1366 N2-(cis-4-{[(lH-indol-3-ylmethyl)amino]methyl}cyclohexyl)-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 433 (M + H) 2
1367 N2-(cis-4- {[(2,5-dimethoxybenzyl)amino]methyl} cyclohexyl)-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 454 (M + H) 2
1368 N2-[cis-4-({ [(4-methoxy-1 -naphthy I)methy ljamino} methy 1)-
cyC1-5hexyl]-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 474 (M + H) 2
1369 N2-[cis-4-({[(5-methoxy-lH-indol-3-yl)methyl]amino}-
methyl)cyclohexyI]-N4,N4-dimethyl-5,6,7,8-tetrahydro-
quinazoline-2,4-diamine 463 (M + H) 1
1370 N2-[cis-4-({[(2-methoxy-l-naphthyl)methyl]amino}methyl)-
cyclohexyl]-N4,N4-dimethyl-5,6,7?8-tetrahydro-
quinazoline-2,4-diamine 474 (M + H) 3
1371 4-bromo-2-({[(cis-4-{[4-(diinethylamino)-5,6,7J8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyI
araino}methyl)-6-methoxyphenol 518 (M + H) 2

433

Ex. No. compound name MS class
1372 N2-[cis-4-({[(5-bromo-lH-indol-3-yl)methylJamino}methyl)-
cyclohexyl]-N4,N4-dimethyl-5,6,7,8-tetrahydro-
quinazo!ine-2,4-diamine 511 (M + H) 1
1373 N2-(cis-4-{[(2,4-dimethoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethyI-5,6,7,8-tetrahydroquinazoline-2,4-diamine 454 (M + H)
1374 N4,N4-dimethyl-N2-(cis-4- {[(2,3,4-trimethoxybenzyl)-
amino]methyl}cyclohexyl)-5,6,7,8-tetrahydro-
quinazoline-2,4-diamine 484 (M + H) ■t
1375 4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]amino}methyl)-
2,6-dimethoxyphenoI 470 (M + H)
1376 N2-(cis-4- {[(3-ethoxy-4-methoxybenzyl)amino]methyl} -
cyC1-5hexyl)-N4,N4-dimethyl-5,6,7,8-tetrahydro-
quinazoline-2,4-diamine 468 (M + H) 1
1377 N4,N4-dimethyI-N2-(cis-4-{[({3-[4-(trifluoromethyl)phenyl]-lH-
pyrazoI'4-yl}methyI)amino]methyl}cyclohexyl)-5,6,7,8-
tetrahydroquinazoline-2,4-diamine 528 (M + H) 2
1378 N4,N4-dimethyl-N2-(cis-4-{[(3,4,5-
trimethoxybenzyl)amino]methyl}cyclohexyl)-5,6,7,8-
tetrahydroquinazoline-2,4-diamine 484 (M + H) 2
1379 N4,N4-dimethyl-N2-(cis-4-{[(pentamethylbenzyl)amino]-
methyl}cyclohexyl)-5,6,7,84etrahydroquinazoline-2,4-diamine 464 (M + H)
1380 N2-(cts-4-{[(3,5-dimethoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethy]-5,6,7,8-tetrahydroquinazoline-2,4-diamine 454 (M + H) 2
1381 4-({[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]amino}methyl)-
2-iodo-6-methoxyphenol 566 (M + H) 1
1382 4-( {[(cis-4- {[4-(dimethy lamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methyllamino}methyl)-2,6-dimethylphenol 438 (M + H) 2
1383 N2-(cis-4-{[(4-methoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethyl-5,6,7,84etrahydroquinazoIine-2,4-diamine 424 (M + H) 3
1384 N2-(cis-4- {[(2,3-dihydro-1,4-benzodioxin-6-
ylmethyl)amino]methyI}cyclohexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroq uinazoli ne-2,4-d iam i ne 452 (M + H)
1385 N2-(cis-4-{[(3-bromoben2yl)amino]methyl}cyC1-5hexyl)-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 472 (M + H) 3
1386 N2-(cis-4-{[(5-bromo-2,4-dimethoxybenzyI)amino]methyl}-
cyclohexyl)-N4>N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 532 (M + H) -i
1387 N2-(cis-4-{[(5-bromo-2-methoxybenzyl)amino]methyl}-
cyclohexyi)-N4,N4-dimethyi-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 502 (M + H) -i
1388 3-chloro-4-({[(cis-4-{[4-(dimethylamino)-5!6,7,8-
tetrahydroquinazoIin-2-y!]amino}cyclohexyl)methyl]amino}-
methyl)phenol 444 (M + H) 2
1389 2-({[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino} cyclohexyl)methyl]amino} methyl)benzonitrile 419 (M + H) 3

434

Ex. No. compound name MS class
1390 N2-(cis-4-{[(3-chlorobenzyI)amino]methyI}cyC1-5hexyl)-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline'2,4-diamine 428 (M + H)
1391 N2-(cis-4-{[(4-chIorobenzyl)amino]methyi}cyclohexyl)-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazo!ine-2,4-diamine 428 (M + H)
1392 N2'[cis-4-({[4-(diethylamino)benzyI]amino}methyl)cyC1-5hexyl]-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 465 (M + H) 2
1393 N2-[cis-4-({[4-(dimethyIamino)benzyl]amino}methyI)-
cyclohexyl]-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 437 (M + H)
1394 N2-[cis-4-( {[(9-ethyl-9H-carbazoI-3-yI)methyI]amino} -
methyl)cyC1-5hexyl]-N4,N4-dimethyI-5,6,7,8-tetrahydro-
quinazoline-2,4-diamine 511 (M + H)
1395 N2-[cis-4-({[2-fluoro-5-(trifluoromethyl)benzyl]amino}-
methyi)cyclohexyl]-N4,N4-dimethyl-5,6,7,8-tetrahydro-
quinazoline-2,4-diamine 480 (M + H) 3
1396 4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]amino}methyl)phenol 410 (M + H)
1397 [5-({[(cis-4-{[4-(dimetbylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]amino}methyI)-2-furyllmethanol 414 (M + H) 3
1398 N2-(cis-4-{[(4-isopropoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 452 (M + H) 3
1399 N2-[cis-4-( {[(5-ethyl-2-thienyl)methyl]amino} methy 1)-
cyclohexyl]-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 428 (M + H) 3
1400 N2-(cis-4-{[(3,3-diphenylprop-2-en-l-yl)amino]methyl}-
cyclohexyl)-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 496 (M + H) 1
1401 4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyllamino}methyl)-2-ethoxyphenol 454 (M + H) 2
1402 N2-{cis-4-[({[4-(dimethylamino)-l-naphthyl]methyl}amino)-
methyl]cyclohexyl}-N4,N4-dimethyl-5,6,7,8-tetrahydro-
quinazoline-2,4-diamine 487 (M + H) 2
1403 N4,N4-dimethyI-N2-(cis-4-{[(2,4,6-trimethoxybenzyl)-
amino]methyl}cyc!ohexyl)-5,6,7,8-tetrahydroquinazoline-
2,4-diamtne 484 (M + H) 1
1404 2-bromo-4-chloro-6-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]ammo}cyclohexyl)methyl]-
amino}methyl)phenol 522 (M + H) 2
1405 3-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methyllamino}methyl)benzonitrile 419 (M + H) -i
1406 N2-(cis-4- {[(2-fluoro-5-methoxybenzy I)amino]methyl} -
cyclohexyI)-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 442 (M + H) 3
1407 N4,N4-dimethyl-N2-{cis-4-[({2-[(trifluoromethyl)thio]-
benzyl}amino)methyI]cyC1-5hexyi}-5,6,7,8-tetrahydro-
quinazoline-2,4-diamine 494 (M + H) 3

435

Ex. No. compound name MS class
1408 N2-(cis-4-{[(5-bromo-2-ethoxybenzyl)amino]methy!}-
cyclohexyl)-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 516 (M + H)
1409 N2-(cis-4-{[(2,4-dimethoxy-3-methyIbenzyl)amino]methyi}-
cyC1-5hexyl)-N4,N4-dimethyI-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 468 (M + H)
1410 N4,N4-dimethyl-N2-[cis-4-( {[2-(trifluoromethoxy)benzyl]-
amino}methyl)cyclohexyl]-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 478 (M + H) 3
1411 N2-(cis-4-{[(2,5-diethoxybenzyl)amino]methyl}cyC1-5hexyl)-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 482 (M + H) 1
1412 N2-(cis-4- {[(2,4-diethoxybenzyl)amino]methyl} cyclohexyl)-
N4,N4-dimethyl-5,6,7,8-tetrahydroqirinazoline-2,4-diamine 482 (M + H) 1
1413 N2-(cis-4- {[(3,5-dibromo-2-methoxybenzyI)amino]methyl} -
cyclohexyl)-N4,N4-dimethyi-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 580 (M + H) 1
1414 N2-[cis-4-( {[2-(difluoromethoxy)benzyl]amino} methy 1)-
cyclohexyl]-N4,N4-dimemyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 460 (M + H) 3
1415 N2-(cis-4-{[(5-fluoro-2-methoxybenzyl)amino]methyl}-
cyC1-5hexyl)-N4,N4-dimethyI-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 442 (M + H)
1416 N4,N4-dimethyI-N2-(cis-4-{[(2,4,54riethoxybenzyl)amino]-
methyl}cyclohexyl)-5,6,7,8-tetrahydroquinazoline-2,4-diamine 526 (M + H) 1
1417 N4,N4-dimethyl-N2-(cis-4-{[(2,4,5'trimethoxybenzyl)amino]-
methyl}cyclohexyl)-5,6,7,8-tetrahydroquinazoline-2,4-diamine 484 (M + H) 1
1418 N2-(cis-4-{[(2,3-dimethoxybenzyl)ammo]methyl}cyclohexyl)-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoIine-2,4-diamine 454 (M + H) 3
1419 N2-[cis-4-( {[2-(alIyIoxy)benzyl]amino} methy l)cyclohexyl]-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 450 (M + H) 3
1420 N2-(cis-4-{[(l-benzothien-3-ylmethyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 450 (M + H) ^
1421 N4,N4-dimethy l-N2-[cis-4-( {[(1 -methy 1- lH-indol-3-
yI)methyl]amino}methyI)cyc!ohexyl]-5,6,7,8-
tetrahydroquinazoIine-2,4-diamine 447 (M + H) 3
1422 N4,N4-dimethyl-N2-[cis-4-({[(5-methyl-2-thienyl)methyl]-
amino}methyl)cyc!ohexyl]-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 414 (M + H) ->
1423 N2-{cis-4- {[(mesitylmethy I)amino]methyl} cyc!ohexyl)-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 436 (M + H)
1424 N2-(cis-4- {[(1,3-benzodioxol-5-ylmethyl)amino]methy I }-
cyclohexyl)-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 438 (M + H)
1425 N4,N4-dimethyl-N2-(cis-4- {[(3-thienylmethy l)amino]methy 1} -
cyclohexyl)-5,6,7,8-tetrahydroquinazoline-2,4-diamine 400 (M + H) ">
1426 N4,N4-dimethyI-N2-(cis-4-{[(3-methylbenzyl)amino]methyl}-
cyclohexyl)-5,6,7,8-tetrahydroquinazoline-2,4-diamine 408 (M + H) ->

436

Ex. No- compound name MS class
1427 N4,N4-dimethyl-N2-(cis-4-{[(2-methylbenzyl)amino]methyl}-
cyclohexyl)-5,6J,8-tetrahydroquinazoIine-2,4-diamine 408 (M + H) ->
1428 N4,N4-dimethyl-N2-(cis-4-{[(4-methylbenzyl)amino]methyI}-
cyc I oh exy I)-5,6,7,8-tetrahydroq u i nazol ine-2,4-d i am i n e 408 (M + H) J
1429 N2-(cis-4- {[(3,5-dichlorobenzyI)amino]methyl} cyclohexyl)-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 462 (M + H) ->
1430 N2-[cis-4-( {[{7-methoxy-1,3-benzodioxol-5-yl)methy IJamino} -
methyI)cyclohexyl]-N4,N4-dimethyI-5,6,7,8-tetrahydro-
quinazoline-2,4-diamine 468 (M + H) 2
1431 N2-(cis-4-{[(3-bromo-4,5-dimethoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoIine-
2,4-diamine 532 (M + H)
1432 N2-(cis-4- {[(4-methoxy-3-methy lbenzyl)amino]methy I} -
cyclohexyl)-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-dtamine 438 (M + H) i
1433 N2-(cis-4-{[(2-bromo-4,5-dimethoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 532 (M + H)
1434 N4,N4-dimethyl-N2-[cis-4-( {[(2-methyl-5-phenyl-3-
furyI)methyl]amino}methyl)cyclohexyl]-5,6,7,8-
tetrahydroquinazoline-2,4-diamine 474 (M + H) 3
1435 N2-(cis-4-{[(3,4-dimethoxybenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 454 (M + H) i
1436 4-({[(ciS'4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyllamino}methyI)-2-methylphenol 424 (M + H) 2
1437 N2-(cis-4-{[(4-methoxy-2,5-dimethyibenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 452 (M + H) 2
1438 2-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino)cyclohexyl)methyIlamino}methyl)-6-raethoxyphenol 440 (M + H) ->
1439 N2-[cis-4-({[3-chloro-2-fluoro-5-(trifluoromethyl)benzylj-
amino}methyl)cyclohexyl]-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazol ine-2,4-d i am ine 514 (M + H) ->
1440 N2-[cis-4-({[3-fluoro-5-(trifluoromethyi)benzyl]amino}-
methyl)cyclohexyl]-N4,N4-dimethyl-5,6,7,8-tetrahydro-
q u inazoline-2,4-diamine 480 (M + H)
1441 4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yl]amino}cyclohexyl)methyl]amino}methyl)-2-fIuoro-
6-methoxyphenol 458 (M + H) 2
1442 N2-(cis-4-{[(2-fluoro-4,5-dimethoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 472 (M + H) 3
1443 N2-(cis-4-{[(2~ethylbenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 422 (M + H) 3
1444 3-[[4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yl]amino}cyclohexyl)methyl]amino}methyl)phenyl](methyl)-
amino]propanenitrile 476 (M + H) 3

437

Ex. No. compound name MS class
1445 N2-{cis-4-[({4-[(4-bromobenzyl)oxy]benzyl}amino)methyl]-
cyc!ohexyl}-N4,N4-dimethyI-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 578 (M + H) 3
1446 N2-(cis-4-{[(3,5-dibromo-2-ethoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 594 (M + H)
1447 N2-(cis-4-{[2-(4-bromophenyl)ethyI]amino}cyC1-5hexyl)-N4,N4~
dimethylquinoline-2,4-diamine 467 (M + H) ->
1448 N2-(cis-4-{[2-(3-chlorophenyl)ethyl]amino}cyC1-5hexyI)-N4,N4-
dimethyIquinoline-2,4-diamine 423 (M + H) -
1449 N2-(cis-4-{[2-(2-chlorophenoxy)ethyl]amino}cyC1-5hexyl)-
N47N4-dimethylquinoline-2,4-diamine 439 (M + H) 3
1450 N2-{cis-4-[(2-methoxy-2-phenylethyl)amino]cyclohexyl}-N4,N4-
dimethylquinoline-2,4-diamine 419 (M + H) "i
1451 N4,N4-Dimethyl-N2-[4-(pentamethylphenylmethyl-amino)-
cyclohexyl]-quinoline-2,4-diamine 445 (M + H) 3
1452 N2-{cis-4-[(3-ethoxybenzyI)amino]cyclohexyl}-N4,N4-
dimethylquinoline-2,4-diamine 419 (M + H)
1453 N2-(cis-4-{[(2S)-2,3-bis(benzyloxy)propyl]amino}cyclohexyl)-
N4,N4-dimethylquinoline-2,4-diamine 539 (M + H) -i
1454 N2-(cis-4-{[(3-methoxy-2-naphthyl)methyl]amino}cyclohexyl)-
N4,N4-dimethylquinoIine-2,4-diamine 455 (M + H) ->
1455 3-{ {2-[(cis-4- {[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)amino]ethyl}(phenyl)aminolpropanenitrile 457 (M + H) 2
1456 N-{(lS)-l-benzyl-2-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)aminolethyl}-4-methylbenzenesulfonamide 572 (M + H) 3
1457 (2- {[4-(4-Dimethylamino-quinoIin-2-y lamino)-cyclohexy lamino]-
methyl}-cyclohexyl)-phenyl-methanol 487 (M + H) 3
1458 N2-(cis-4-{[2'(3,5-dimethoxyphenyl)ethyl]amino}cyclohexyl)-
N4,N4-dimethylquinoline-2,4-diamine 449 (M + H)
1459 N4,N4-dimethyl-N2-(cis-4-{[2-(2-phenyl-lH-indol-3-
yI)ethyllamino}cyclohexyI)quinoIine-2,4-diamine 504 (M + H) 2
1460 N2-(cis-4- {[2,2-bis(4-chlorophenyl)ethyl]amino} cyclohexyl)-
N4,N4-dimethylquinoline-2,4-diamine 533 (M + H) 3
1461 (3-{tlS>2-[(cis-4"{[4-(dimethyIamino)quinolin-2-
yl]amino}cyclohexyl)amino]-l-methylethyl}phenyl}-
(phenyl)methanol 509 (M + H) ->
1462 N2-[cis-4-( {[ 1 -(dipheny lmethyl)azetidin-3-y l]methyl} amino)-
cyclohexyll-N4,N4-dimethylquinoline-2,4-diamine 520 (M + H) 1
1463 N2-[cis-4-({[2-(4-bromophenyl)ethyl]amino}methyI)cyC1-5hexyl]-
N4,N4-dimethylquinoIine-2,4-diamine 481 (M + H) 3
1464 N2-[cis-4-( {[4-(4-methoxyphenyl)butyl]amino} methyl)-
cyC1-5hexyll-N4,N4-dimethy!quinoline-2,4-diamine 461 (M + H) i
1465 N4,N4-dimethyl-N2-(cis-4-{[(6-
phenylhexyl)aminolmethyl}cyclohexyl)quinoline-2,4-diamine 459 (M + H) 3
1466 N2-(cis-4-{[(2-mesitylethyl)amino]methyI}cyclohexyl)-N4,N4-
dimethylquinoline-2,4-diamine 445 (M + H) 3

438

Ex. No. compound name MS class
1467 N4,N4-dimethyl-N2-(cis-4-{[(8-
phenyIoctyl)aminolmethyi}cyclohexvl)quinoline-2,4-diamine 487 (M + H) -t
1468 N2-[cis-4-( {[2-(4-tert-butyipheny l)ethy IJamino} methyl)-
cyclohexyI]-N4,N4-dimethylquinoline-2,4-diamine 459 (M + H) 3
1469 N4,N4-dimethyl-N2-(cis-4-{[(5-phenylpent-4-yn-l-
yl)amino]methyl}cyclohexyI)quinoline-2,4-diamine 441 (M + H) 3
1470 N2-[cis-4-({[2-(2-methoxyphenyl)ethyi]amino}methyl)-
cyC1-5hexyll-N4,N4-dimethylquinotine-2,4-diamine 433 (M + H)
1471 N4,N4-dimethyl-N2-(cis-4-{[(3-
phenoxypropyl)amino]methyl}cyclohexyl)quinoline-2,4-diamine 433 (M + H) 3
1472 N4,N4-dimethyl-N2-(cis-4-{[(2,3,5,6-tetrafluorobenzyl)-
aminolmethyl}cyC1-5hexyI)quinoline-2,4-diamine 461 (M + H) ->
1473 N2-(cis-4-{ [(2,5-dichlorobenzyl)amino] methyl }cyclohexyl)-
N4,N4-dimethyIquinoline-2.4-diamine 457 (M + H) 3
1474 N2-(cis-4-{[(5-chloro-2-methoxybenzyI)amino]methyl}-
cyclohexyl)-N4,N4-dimethy!quinoIine-2,4-diamine 453 (M + H) ->
1475 N2-fcis-4-{[(4-chIoro-2-methoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethylquinoline-2,4-diamine 453 (M + H) -i
1476 N2-(cis-4-{[(3-iodo-4-methylbenzyl)amino]methyl}cyclohexyl)-
N4,N4-dimethyIquinoline-2,4-diamine 529 (M + H) 3
1477 N2-[cis-4-({[(2S)-2-(dibenzylamino)propyl]amino}raethyl)-
cyclohexyl]-N4,N4-dimethvIqutnoline-2,4-diamine 536 (M + H) 3
1478 N4,N4-dimethyl-N2-[cis-4-( {[(1 -phenyl-5-propyl-1 H-pyrazol-4-
yI")methyllamino}methyl)cyclohexyl]quinoline-2,4-diamine 497 (M + H) 1
1479 N2-{cis-4-[({[l-(4-chlorophenyl)-5-propyl-lH-pyrazo!-4-
yl]methyl}amino)methyl]cyC1-5hexyl}-N4,N4-dimethylquinoline-
2,4-diamine 531 (M + H) 1
1480 N4,N4-dimethyl-N2-[cis-4-({[4-(4-nitrophenyl)butyl]-
amino}methyl)cyC1-5hexyl]quinoIine-2,4-diamine 476 (M + H) 3
1481 N2-(cis-4-{[2-(4-bromophenyl)ethyI]amino}cyclohexyl)-N4,N4-
dimethyI-5,6,7,8-tetrahydroquinazoline-2,4-diamine 472 (M + H) 3
1482 N2-(cis-4-{[2-(3-chlorophenyl)ethyl]amino}cyclohexyl)-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 428 (M + H) 3
1483 N2-{cis-4-[(2-methoxy-2-phenyIethyI)amino]cyclohexyl}-N4,N4-
dimethyI-5,6,7,8-tetrahydroquinazoline-2,4-diamine 424 (M + H)
1484 N2 - [4-( 2 -Methoxy-2 -pheny 1-ethylam i no)-cyc 1 oh exy 1] -N4 ,N4-
dimethyI-5,6,7,8-tetrahydro-quinazoline-2,4-diamine 424 (M + H) ■■>
1485 N4,N4-Dimethyl-N2-[4-(pentamethylphenylmethyI-amino)-
cyC1-5hexyll-5,6,7,8-tetrahydro-quinazoline-2,4-diamine 450 (M + H) 2
1486 N2-{cis-4-[(3-ethoxybenzyl)amino]cyclohexyl}-N4,N4-dimethyl-
5,6,7,8-tetrahydroquinazoline-2,4-diamine 424 (M + H) ->
1487 N2-(cis-4-{[(2S)-2,3-bis(benzyloxy)propyl]amino}cyclohexyl)-
N4,N4-dimethyI-5T6,7,8-tetrahydroquinazoline-2,4-diamine 544 (M + H) 3
1488 N2-(cis-4-{[(3-methoxy-2-naphthyI)methyl]amino}cyclohexyl)-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 460 (M + H) i
1489 3-[{2-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-
2-yl]amino}cyclohexyI)amino]ethyl}(3-methylphenyl)-
aminolpropanenitrile 476 (M + H) 2

439

Ex. No. compound name MS class
1490 3-[{2-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-
2-yl]amino}cyclohexyl)amino]ethyl}(phenyl)amino]-
propanenitrile 462 (M + H) 1
1491 N-{(lS)-l-ben2yl-2-[{cis-4-{[4-(dimethy]amino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)amino]ethyl}-4-
methylbenzenesulfonamide 577 (M + H) 1
1492 (2-{[4-(4-Dimethylamino-5,6,7,8-tetrahydro-quinazolin-
2-ylamino)-cyclohexyIamino]-methyl}-cyclohexyl)-
phenyl-methanol 490 (M + H)
1493 N2-(cis-4-{[2-(3,5-dimethoxyphenyl)ethyl]amino}cyclohexyI)-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 454 (M + H) 2
1494 N4,N4-dimethyl-N2-{cis-4-{[2-(2-phenyl-lH-indol-3-
yl)ethyl]amino}cyclohexyI)-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 509 (M + H)
1495 N2-(cis-4- {[2,2-bis(4-chlorophenyl)ethy l]amino} eye lohexyl)-
N4 ,N4-d i methy 1- 5,6,7,8-tetrahydroq u i nazo line-2,4-diamine 538 (M + H)
1496 (3-{(lS)-2-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)amino]-l-
methylethy 1} phenvl)(phenvl)methanol 512 (M + H) 3
1497 N2-[cis-4-({[l-(diphenylmethyl)azetidin-3-yl]methyl}amino)-
cyC1-5hexyl]-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 525 (M + H) 1
1498 N2-[cis-4-( {[2-(4-bromophenyl)ethyl]amino} methy I)cyclohexyl]-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 486 (M + H)
1499 N2-[cis-4-({[4-(4-methoxyphenyl)butyl]amino}methyI)-
cyC1-5hexy!]-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 466 (M + H) 3
1500 N4,N4-dimethyI-N2-(cis'4-{[(6-phenylhexyl)amino]methyl}-
cy c loh exy 1)- 5,6,7,8-tetrahy droq u i nazo 1 i ne-2,4 -d i am ine 464 (M + H) 3
1501 N2-(cis-4-{[(2-mesitylethyl)amino]methyl}cyclohexyl)-N4!N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 450 (M + H)
1502 N4,N4-dimethyl-N2-(cis-4-{[(8-phenyloctyI)amino]methyl}-
cyclohexyl)-5,6,7,8-tetrahydroquinazoline-2,4-diamine 492 (M + H) 3
1503 N2-[cis-4-({[2-(4-tert-butylphenyl)ethyI]amino}methyl)-
cyclohexyl]-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 464 (M + H) 3
1504 N2-[cis-4-({[2-(2-methoxyphenyl)ethyl]amino}methyl)-
cyclohexyl]-N4,N4-dimethyI-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 438 (M + H) -i
1505 N4,N4-dimethyl-N2-(cis-4-{[(3-phenoxypropyl)amino]-
methyl}cyclohexyI)-5,6,7,8-tetrahydroquinazoiine-2,4-diamine 438 (M + H) 3
1506 N2-(cis-4-{[(5-chloro-2-methoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethyi-5,6,7!8-tetrahydroquinazoline'
2,4-diamine 458 (M + H)
1507 N2-tcis-4-{[(4-chloro-2-methoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-
2,4-diamine 458 (M + H) i

440

Ex. No. compound name MS class
1508 N2-(cis-4-{[(3-iodo-4-methylbenzyl)amino]methyl}cyC1-5hexyl)-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine 534 (M + H) -t
1509 N2-[cis-4-({[(2S)-2-(dibenzylamino)propyl]amino}methyl)-
cyclohexyl]-N4,N4-dimethyl-5>6,7,8-tetrahydroquinazoline-
2,4-diamine 541 (M + H) -i
1510 N4,N4-dimethy l-N2-[cis-4-( {[(1 -pheny I-5-propy 1-1 H-pyrazol-4-
yl)methyI]amino}methyl)cyc!ohexyl]-5,6,7,8-
tetrah y droq u i n azo 1 i n e-2,4 -d i am i ne 502 (M + H) 1
1511 N2-{cis-4-[({[l-(4-chlorophenyI)-5-propyl-lH-pyrazol-4-
yl]methyI}amino)methyl]cyclohexyl}-N4,N4-dimethyl-5,6,7,8-
tetrahy droq u i nazo 1 i n e-2,4 -d i am i n e 536 (M + H) 1
1512 N4,N4-dimethy l-N2-[cis-4-( {[4-(4-nitrophenyl)butyI]amino} -
methyl)cyclohexyl]-5,6,7,8-tetrahydroquinazoline-2,4-diamine 481 (M + H) *>
1513 N2-(cis-4-{[2-(4-bromophenyl)ethyl]amino}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine 418 (M + H)
1514 N2-(cis-4-{[2-(3-chlorophenyl)ethyl]amino}cyC1-5hexyl)-N4,N4-
dimethyipyrimidine-2,4-diamine 374 (M + H) 3
1515 N2-(cis-4- {[2-(2-chlorophenoxy)ethyl]amino} cyclohexy 1)-
N4,N4-dimethylpyrimidine-2,4-diamine 390 (M + H)
1516 N2-{cis-4-[(2-methoxy-2-phenylethyl)amino]cyclohexyl}-N4,N4-
dimethylpyrimidine-2,4-diamine 370 (M + H) 3
1517 N2-[4-(2-Methoxy-2-phenyl-ethylamino)-cyclohexyl]-N4,N4-
dimethyl-pyrimidine-2,4-diamine 370 (M + H) ->
1518 N2-(cis-4-{[2-(4-bromophenoxy)ethyI]amino}cyclohexyl)-
N4,N4-dimethylpyrimidine-2,4-diamine 434 (M + H) 3
1519 N45N4-Dimethyl-N2-[4-(pentamethyIphenyImethyl-amino)-
cyC1-5hexyl"|-pyrimidine-2,4-diamine 396 (M + H) 3
1520 N2-{cis-4-[(3-ethoxybenzyl)amino]cyclohexyI}-N4,N4-
dimethyIpyrimidine-2,4-diamine 370 (M + H) 3
1521 N2-(cis-4-{[(2S)-2,3-bis(benzyloxy)propyl]amino}cyclohexyl)-
N4,N4-dimethylpyrimidine-2,4-diamine 490 (M + H) "i
1522 N2-(cis-4-{[(3-methoxy-2-naphthyI)methyl]amino}cyclohexyI)-
N4,N4-dimethyIpyrimidine-2.4-diamine 406 (M + H) 3
1523 3-[{2-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)amino]ethyl}(3-methylphenyl)-
aminolpropanenttrile 422 (M + H)
1524 3-[{2-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)amino]ethyl}(phenyl)amino]propanenitrile 408 (M + H)
1525 N2-[cis-4-( {[4-(4-methoxypheny l)butyl]amino} methyl)-
cyclohexyl]-N4,N4-dimethylpyrimidine-2,4-diamine 412 (M + H) t
1526 N4,N4-dimethy]-N2-(cis-4-{[{6-
phenyIhexyl)aminolmethyl}cyC1-5hexyl)pyrimidine-2,4-diamine 410 (M + H) 3
1527 N2-(cis-4-{[(2-mesitylethyl)amino]methyI}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine 396 (M + H) 3
1528 N4,N4-dimethyl-N2-(cis-4- {[(8-
pheny]octyl)amino]methyl)cyclohexyl)pyrimidine-2,4-diamine 438 (M + H) 3
1529 N2-[cis-4-({[2-(4-tert-butyIphenyl)ethyI]amino}methyl)-
cyclohexyl]-N4,N4-dimethylpyrimidine-2,4-diamine 410 (M + H) 3

441

Ex. No. compound name MS class
1530 N4,N4-dimethyl-N2-( cis-4- {[(5-phenylpent-4-yn-1 -
yl)amino]methyI}cyclohexyl)pyrimidine-2,4-diamine 392 (M + H)
1531 N2-[cis-4-({[2-(2-methoxyphenyl)ethyl]amino}rnethyl)-
cyclohexyI]-N4,N4-dimethylpyrimidine-2,4-diamine 384 (M + H) -i
1532 N4,N4-dimethyl-N2-(cis-4-{[(3-phenoxypropyl)amino]-
methyl}cyclohexyI)pyrimidine-2,4-diamine 384 (M + H) ->
1533 N4,N4-dimethyI-N2-(cis-4-{[(2,3,5,6-tetrafluorobenzyl)amino]-
methyl)cyclohexyl)pyrimidine-2,4-diamine 412 (M + H) 3
1534 N2-(cis-4-{[(2,5-dichlorobenzyl)amino]methyl}cyC1-5hexyl)-
N4,N4-dimethyIpyrimidine-2.4-diamine 408 (M + H) ->
1535 N2-(cis-4-{[(5-chloro-2-methoxybenzyl)amino]methyl}-
cyclohexyl)-N4,N4-dimethylpyrimidine-2,4-diamine 404 (M + H)
1536 N2-(cis-4-{[(4-chloro-2-methoxybenzyl)amino]methyl}-
cyC1-5hexyi)-N4,N4-dimethy]pyrimidine-2,4-diamine 404 (M + H)
1537 N2-(cis-4-{[(3-iodo-4-methylbenzyI)amino]methyl}cyclohexyl)-
N4,N4-dimethyIpyrimidine-2,4-diamine 480 (M + H)
1538 N2-[cis-4-({[(2S)-2-(dibenzyIamino)propyl]amino}methyl)-
cyclohexyll-N4,N4-dimethylpyrimidine-2,4-diamine 487 (M + H)
1539 2-(benzyloxy)ethyl (cis-4- {[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)carbamate 463 (M + H)
1540 2,2-dimethylpropyl (cis-4-{[4-(dimethylamino)quinolin-2-
yllamino\cyclohexyl)carbamate 399 (M + H)
1541 "[4-(4-Dimethylamino-quinoIin-2-ylamino)-cyC1-5hexyI]-carbamic
acid 4,5-dimethoxy-2-nitro-benzyl ester 524 (M + H) 2
1542 3-(trifluoromethyl)phenyl (cis-4-{[4-(dimethylamino)quinolin-2-
yllamino)cyclohexyi)carbamate 473 (M + H)
1543 4-bromophenyl (cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)carbamate 483 (M + H) *>
1544 2-methoxyphenyl (cis-4-{[4-(dimethylamino)quinolin-2-
yl~|amino)cyclohexyl)carbamate 435 (M + H) 3
1545 2-methoxyethyl (cis-4- {[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)carbamate 387 (M + H) 3
1546 octyl (cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)carbamate 441 (M + H) ->
1547 ethyl (cis-4- {[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)carbamate 357 (M + H) 3
1548 [4-(4-Dimethylamino-quinolin-2-ylamino)-cyclohexyl]-carbamic
acid 4-nitro-benzyl ester 464 (M + H) ■>
1549 2-naphthyI (cis-4-{ [4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)carbamate 455 (M + H)
1550 ally 1 (cis-4- {[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexy!)carbamate 369 (M + H) ->
1551 [4-(4-Dimethylamino-quinoIin-2-yIamino)-cyclohexyl]-carbamic
acid benzyl ester 419 (M + H)
1552 phenyl (cis-4-{[4-(dimethyIamino)quinolin-2-
yllamino}cyclohexyl)carbamate 405 (M + H) 3
1553 (1 R,2S,5R)-2-isopropy 1-5-methy lcyclohexy 1 (cis-4- {[4-
(dimethylamino)quinolin-2-yllamino}cyclohexyl)carbamate 467 (M + H) -i

442

Ex. No. compound name MS class
1554 4-methylphenyl (cis-4-{[4-(dimethylamino)quinoIin-2-
yllamino} cyclohexyOcarbamate 419 (M + H) -i
1555 methyl (cis-4-{[4-(dimethylamino)quinolin-2-
yr|amino{cyclohexyl)carbamate 343 (M + H) ■~>
1556 2-chlorobenzyl (cis-4-{ [4-(dimethylamino)quinolin-2-
yllamino} cyclohexyl)carbamate 453 (M + H)
1557 9H-fluoren-9-ylmethyl (cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexvi)carbamate 507 (M + H)
1558 2,2,2-trichIoroethy] (cis-4-{[4-(dimethylamino)quinolin-2-
yl"|amino}cyclohexyl)carbamate 459 (M + H) 3
1559 2-(benzyloxy)ethyl [(cis-4-{ [4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)rnethyl"|carbamate 477 (M + H) -I
1560 2,2-dimethylpropyI [(cis-4-{[4-(dimethylamino)quinolin-2-
ynamino}cyclohexyl)methyl]carbamate 413 (M + H)
1561 4,5-dimethoxy-2-nitrobenzyl [(cis-4-{[4-(dimethylamino)-
quinoIin-2-yI]amino}cyclohexyl)methyl]carbamate 538 (M + H) 3
1562 3-(trifluoromethyl)phenyl [(cis-4-{[4-(dimethylamino)quinoIin-2-
yl]amino}cyclohexyl)methyl]carbamate 487 (M + H) 3
1563 4-bromophenyl [(cis-4-{ [4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyl]carbamate 497 (M + H)
1564 2-methoxyphenyl [(cis-4-{ [4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyllcarbamate 449 (M + H) 3
1565 2-methoxyethyl [(cis-4- {[4-(dimethylamino)quinolin-2-
yl1amino}cyc!ohexvl)methyllcarbamate 401 (M + H) ■y
1566 octyl [(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyllcarbamate 455 (M + H) 3
1567 ethyl [(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cvclohexyl)methyl"|carbamate 371 (M + H) 3
1568 4-nitrobenzyl [(cis-4- {[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyllcarbatnate 478 (M + H) 3
1569 2-naphthyl [(cis-4-{[4-(dimethylamino)quinoIin-2-
yl]amino}cyclohexyl)methyllcarbamate 469 (M + H) 3
1570 allyl [(cis-4-{ [4-(dimethytamino)quinoIin-2-
yl]amino}cyclohexyl)methyl]carbamate 383 (M + H)
1571 ben2yl [(cis-4- {[4-(dimethylamino)quinolin-2-
ynamino}cyclohexyl)methyllcarbamate 433 (M + H) ->
1572 phenyl [(cis-4-{ [4-(dimethylamino)quinolin-2-
yllaminolcyclohexyl)methyllcarbamate 419 (M + H) t
1573 (I R,2S,5R)-2-isopropyl-5-methylcyclohexyl [(cis-4-
{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-
carbamate 481 (M + H) ~>
1574 4-methylphenyl [(cis-4- {[4-(dimethylamino)quinolin-2-
yllamino)cyclohexyl)methyl]carbamate 433 (M + H) 3
1575 methyl [(cis-4-{ [4-(dimethylamino)quinolin-2-
yl]amino)cyclohexyl)methyl]carbamate 357 (M + H) ">
1576 2-chlorobenzyl [(cis-4-{ [4-(dimethylamino)quinolin-2-
ynamino}cyclohexyl)methyl]carbamate 467 (M + H) 3

443

Ex. No. compound name MS class
1577 9H-fluoren-9-ylmethyl [(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyl1carbamate 521 (M + H)
1578 2,2,2-trichloroethyI [(cis-4-{ [4-(dimethy!arnino)quinolin-2-
yl]amino}cyclohexyl)methyncarbamate 473 (M + H) 3
1579 2-(benzyloxy)ethyl (cis-4-{ [4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)carbamate 468 (M 4- H) 3
1580 2,2-dimethylpropyl (cis-4-{ [4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)carbamate 404 (M + H) 3
1581 [4-(4-Dimethylamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-
cyclohexyl]-carbamic acid 4,5-dimethoxy-2-nitro-benzyl ester 529 (M + H) 2
1582 3-(trifluoromethyl)phenyl (cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)carbamate 478 (M + H) 3
1583 4-bromophenyl (cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-y!lamino}cyclohexyl)carbamate 488 (M + H) 3
1584 2-methoxyphenyl (cis-4-{[4-(dimethy!amino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)carbamate 440 (M + H) -*
1585 2-methoxyethyl (cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)carbamate 392 (M + H) 3
1586 octyl (cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexvl)carbamate 446 (M + H) 3
1587 ethyl (cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino) cyclohexyl)carbamate 362 (M + H)
1588 4-nitrobenzyl (cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)carbamate 469 (M + H)
1589 2-naphthyl(cis-4-{[4-(dimetbylamino)-5,6,7,8-
tetrahydroquinazolin-2-y!lamino}cyclohexyl)carbamate 460 (M + H)
1590 allyl (cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexvl)carbamate 374 (M + H)
1591 benzyl (cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yllamino)cyclohexyI)carbamate 424 (M + H)
1592 phenyl(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yl]amino}cyclohexyl)carbamate 410 (M + H) 1
1593 (2S,5R)-2-isopropyl-5-methylcyclohexyl (cis-4-{ [4-
(dimethylamino)-5T6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)carbamate 472 (M + H) ^>
1594 4-methylphenyl {cis-4-{[4-(dimethyiamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino)cyclohexyl)carbamate 424 (M + H)
1595 methyl (cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-
2-yl]amino}cyclohexyI)carbamate 348 (M + H) 3
1596 2-chlorobenzyl (cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexvl)carbamate 458 (M + H) ->
1597 9H-fluoren-9-ylmethyI (cis-4-{ [4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yIlamino)cyC1-5hexyl)carbamate 512 (M + H) 3
1598 2,2,2-trichloroethyl(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)carbamate 464 (M + H)
1599 2-(benzyloxy)ethyl [(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)methyllcarbamate 482 (M + H)

444

Ex. No. compound name MS class
1600 2,2-dimethylpropyl [(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin^-yllaminolcvclohexynmethvllcarbamate 418 (M + H) ->
j
1601 4,5-dimethoxy-2-nitrobenzyl [(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)methyllcarbamate 543 (M + H) 1602 3-(trifluoromethyl)phenyI [(cis-4-{[4-(dimethylarnino)-5,6,7,8-
tetrahydroquinazo]in-2-yllamino}cyC1-5hexyl)methyllcarbamate 492 (M + H)
1603 4-bromophenyl [(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)methyI]carbamate 502 (M + H) j
1604 2-methoxyphenyl [(cis-4-{[4-(dimethy!amino)-5,6,7,8-
tetrahydroquinazoIin-2-yllamino}cvC1-5hexyl)methyIlcarbamate 454 (M + H)
1605 2-methoxyethyl [(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)methyl]carbamate 406 (M + H)
1606 octy! [(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyl)methyllcarbamate 460 (M + H)
1607 ethyl [(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazo!in-2-
yilamino}cyclohexyl)methyl]carbamate 376 (M + H) 3
1608 [4-(4-Dimethylamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-
cyclohexylmethyl]-carbamic acid 4-nitro-benzyl ester 483 (M + H)
1609 2-naphthyl [(cis-4-{ [4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyC1-5hexyl)methyI~|carbamate 474 (M + H)
1610 allyl [(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexy!)methyllcarbamate 388 (M + H) 3
1611 [4-(4-Dimethylamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-
cyclohexylmethyl 1-carbamic acid benzyl ester 438 (M + H)
1612 phenyl [(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yIlamino}cyC1-5hexyl)methyllcarbamate 424 (M + H)
1613 (2S,5R)-2-isopropyI-5-methylcyclohexyl [(cis-4- {[4-
(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yilamino}cyclohexyl)methyllcarbamate 486 (M + H)
1614 4-methylphenyI [(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)methyllcarbamate 438 (M + H) 3
1615 methyl [(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yl]amino}cyclohexyl)methyncarbamate 362 (M + H)
1616 2-chIorobenzyl [(cis-4-{[4-(dtmethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-ynamino}cyC1-5hexyI)methyllcarbamate 472 (M + H) 3
1617 9H-fluoren-9-ylmethyI[(cis-4-{[4-tdimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino)cyc!ohexyl)methyl]carbamate 526 (M + H) 3
1618 2,2,2-trichloroethyl [(cis-4-{ [4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyllcarbamate 478 (M + H) ->
1619 2-(benzyloxy)ethyl (cis-4-{[4-(dimethylamino)pyrimidin-2-
yl"|amino}cyclohexyl)carbamate 414 (M + H)
1620 2,2-dimethylpropyl (cis-4-{[4-(dimethy]amino)pyrimidin-2-
y!lamino}cyclohexyl)carbamate 350 (M + H)
1621 [4-(4-DimethyIamino-pyrimidin-2-ylamino)-cyclohexyl]-carbamic
acid 4,5-dimethoxy-2-nitro-benzyl ester 475 {M + H)
1622 3-(trifluoromethyl)phenyl (cis-4-{[4-(dimethylamino)pyrimidin-
2-yllamino}cyclohexyI)carbamate 424 (M + H)

445

Ex. No. compound name MS class
1623 4-bromophenyl (cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)carbamate 434 (M + H)
1624 2-methoxyphenyl (cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)carbamate 386 (M + H) j
1625 2-methoxyethyl (cis-4-{[4-(dimethyIamino)pyrimidin-2-
ynamino}cyclohexyl)carbamate 338 (M + H) --l
1626 octyl (cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)carbamate 392 (M + H) ">
1627 ethyl (cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)carbamate 308 (M + H) ■>
1628 4-nitrobenzyl (cis-4-{ [4-(dimethylamino)pyrimidin-2-
yllamino}cyC1-5hexyl)carbamate 415 (M + H) -i
1629 2-naphthyl (cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)carbamate 406 (M + H)
1630 allyl (cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)carbamate 320 (M + H) 3
1631 benzyl (cis-4-{ [4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)carbamate 370 (M + H) 3
1632 pheny 1 (cis-4- {[4-(dimethy lamino)pyrimidin-2-
yllamino}cyclohexyl)carbamate 356 (M + H) 3
1633 (2S,5R)-2-isopropyl-5-methylcyclohexyl (cis~4-{[4-
(dimethylamino)pyrimidin-2-yllamino}cyclohexyl)carbamate 418 (M + H) ">
1634 4-methylphenyl (cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)carbamate 370 (M + H)
1635 methyl (cis-4- {[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)carbamate 294 (M + H)
1636 2-chlorobenzyI (cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)carbamate 404 (M + H)
1637 9H-fluoren-9-ylmethyl (cis-4- {[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)carbamate 458 (M + H) 3
1638 2,2,2-trichloroethy 1 (cis-4- {[4-(dimethy lamino)pyrimidin-2-
yl]amino}cyclohexyl)carbamate 410 (M + H) "i
1639 2-(benzyloxy)ethyI [(cis-4-{ [4-(dimethylamino)pyrimidin-2-
yllamino}cvclohexyl)methyncarbamate 428 (M + H) 3
1640 2,2-dimethylpropyl [(cis-4- {[4-(dimethylamino)pyrimidin-2-
ynamino)cyC1-5hexyl)methyl]carbamate 364 (M + H)
1641 4,5-dimethoxy-2-nitrobenzyl [(cis-4-{[4-(dimethylamino)-
pyrimidin-2-yl]amino}cyclohexyl)methyllcarbamate 489 (M + H)
1642 3-(trifluoromethyl)phenyl [(cis-4-{[4-(dimethylamino)pyrimidin-
2-yl]amino}cyclohexyI)methyl]carbamate 438 (M + H) 3
1643 4-bromophenyl [(cis-4-{ [4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyncarbamate 448 (M + H)
1644 2-methoxyphenyl [(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyc]ohexyl)methyllcarbamate 400 (M + H) j
1645 2-methoxyethyl [(cis-4- {[4-(dimethylamino)pyrimidin-2-
yl]amino)cyclohexyl)methyl]carbamate 352 (M + H) 3
1646 octyl [(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cYclohexyl)methyllcarbamate 406 (M + H) 3

446

Ex. No. compound name MS class
1647 ethyl [(cis-4-{ [4-(dimethylamino)pyrimidin-2-
yilamino}cyclohexyl)methyllcarbamate 322 (M + H)
1648 [4-(4-Dimethyiamino-pyrimidin-2-ylamino)-cyclohexylmethyl]-
carbamic acid 4-nitro-benzyI ester 429 (M + H)
1649 2-naphthyl [fcis-4-{ [4-(dimethyiamino)pyrimidin-2-
y]lamino}cyclohexyl)methyl]carbamate 420 (M + H)
1650 allyl [(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl]arnino}cyclohexyl)rnethyllcarbarnate 334 (M + H) ">
1651 [4-(4-Dimethy!amino-pyrimidin-2-yIamino)-cyC1-5hexylmethyl]-
carbamic acid benzyl ester 384 (M + H) -i
1652 phenyl [(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyllcarbamate 370 (M + H) j
1653 (2S,5R)-2-isopropyI-5-methylcyclohexyl [(cis-4-{[4-
(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)methylj-
carbamate 432 (M + H) 3
1654 4-methylphenyl [(cis-4-{[4-(dimethylamino)pyrimidin-2-
vilamino}cyclohexyl)methyl1carbamate 384 (M + H) 3
1655 methyl [(cis-4-{[4-(dimethylamino)pyrimidin-2-
yilamino)cyclohexyl)methyllcarbamate 308 (M + H)
1656 2-chlorobenzyl [(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyclohexyl)methyncarbamate 418 (M + H)
1657 9H-fluoren-9-ylmethyi [(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino} cyclohexyl)methvllcarbamate 472 (M + H) 3
1658 2,2,2-trichloroethyl [(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyC1-5hexyl)methyllcarbamate 424 (M + H) 3
1659 N-(2-ch!oropheny))-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)urea 443 (M + H)
1660 N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(2,6-dimethylphenyl)urea 437 (M + H) -i
1661 N-(2,4-difluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyI)urea 445 (M + H) 3
1662 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyI)-N'-(2-ethyl-6-methylphenyl)urea 451 (M + H) 1
1663 ethyl N-{ [(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)amino]carbonyl}leucinate 475 (M + H)
1664 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(4-f]uorophenyl)urea 427 (M + H) 2
1665 N-(cis-4-{[4-(dimethylamino)-5?6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-['4-(methyIthio)phenyl]urea 455 (M + H)
1666 N-(cis-4-{[4'(dimethylamrno)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-NI-[2-(trifIuoromethyl)phenyllurea 477 (M + H) 3
1667 N-(cis-4-{[4'(dimethylamino)'5;,6,7,8-tetrahydroquinazolin-2-
y!lamino}cyclohexyl)-N'-mesityIurea 451 (M + H) 1
1668 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(2-methyIphenyl)urea 423 (M + H) 3
1669 N-(cis-4- {[4-(dimethylamino)-5,6,7,8-tetrahydroquinazol in-2-
yllamino}cyclohexyl)-N'-{2,4,6-trichIorophenyl)urea 511 (M + H) 2

447

Ex. No. compound name MS class
1670 N-(cis-4-{[4-tdimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)-NM7A64ribromopheny])urea 642 (M + H) 1
1671 N-(2,4-dibromo-6-fIuorophenyI)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyI)urea 583 (M + H) 2
1672 N-(2,6-diethylphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)urea 465 (M + H) 1
1673 N-[2-chloro-6-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}cyclohexyl)urea 511 (M + H) 3
1674 N-(2-chloro-6-methylphenyI)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahvdroquinazolin-2-yllamino}cyC1-5hexyl)urea 457 (M + H) ■>
1675 N-(2-chlorobenzyl)-Nt-tcis-4-{[4-(dimethylamino)-5,6,758-
tetrahydroquinazolin-2-yt]amino}cyC1-5hexyl)urea 457 (M + H) 2
1676 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(2-ethyl-6-isopropyIphenyl)urea 479 (M + H) 2
1677 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(2-ethylphenyI)urea 437 (M + H) 2
1678 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino)cyclohexyl)-N'-(2-iodophenyl)urea 535 (M + H) 3
1679 N-(cis-4-{[4-(dimethylatnino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)-N'-(2-isopropyl-6-methylphenyl)urea 465 (M + H) 2
1680 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-(2-isopropylphenyl)urea 451 (M + H) 3
1681 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)-N'-(2-methyl-3-nitrophenyl)urea 468 (M + H) 3
1682 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyc]ohexyl)-N'-(2-propylphenyl)urea 451 (M + H) 3
1683 N-(2-tert-butyl-6-methylpheny!)-N'-(cis-4- {[4-(dimethy lamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]araino}cyclohexyl)urea 479 (M + H) 2
1684 N-(2-tert-butylphenyl)-Nf-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)urea 465 (M + H) ->
1685 N-(3-chloro-2-methylphenyI)-N'-(cis-4-{[4-(dimethyIamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)urea 457 (M + H) 3
1686 N-(4-bromo-2,6-difluorophenyl)-N'-(cis-4- {[4-(dimethy lamino)-
5,6,7,8-tetrahydroquinazoiin-2-yl]amino}cyclohexyl)urea 523 (M + H) 3
1687 N-[4-chloro-2-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea 511 (M + H) ~i
1688 N-(4-cyanophenyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea 434 (M + H) 3
1689 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)-N'-(diphenylmethyl)urea 499 (M + H) 1
1690 N-(4-bromo-2,6-dimethylphenyt)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquInazolin-2-yl]amino}cyclohexyI)urea 515 (M + H) 1
1691 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)-N'-(3-niethyl-5-phenylisoxazol-4-yl)urea 490 (M + H) 1
1692 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-[5-methyl-2-(trifluoromethyl)-3-furyl]-
urea 481 (M + H) 3

448

Ex. No. compound name MS class
1693 N-(2-bromopheny])-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yI]arnino}cyclohexyI)urea 487 (M + H) 3
1694 N-biphenyl-2-y]-N'-(ciS'4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexvl)urea 485 (M + H) -i
1695 N-butyl-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yllamino}cyclohexyl)urea 389 (M + H) ">
1696 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y]]amino}cvC1-5hexyl)-N'-(2,3-dimethyIphenyI)urea 437 (M + H) 3
1697 ethyl 3-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyC1-5hexyl)amino]carbonyl}amino)-
benzoate 481 (M + H) 3
1698 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yljamino} cyclohexyl)-N'-[ 1 -(3-isopropenylpheny 1)-1 -methy I-
ethyll-urea 491 (M + H)
1699 methy] N-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-y]]amino}cyclohexyl)amino]carbonyl}methioninate 479 (M + H) 3
1700 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cvclohexyl)-N'-l-naphthylurea 459 (M + H) 2
1701 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
vllamino}cyC1-5hexy])-N'-[(2S)-2-phenylcyclopropyI]urea 449 (M + H) -i
1702 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(4-phenoxyphenyl)urea 501 (M + H) -i
1703 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yI]amino}cvC1-5hexyl)-N'-pentylurea 403 (M + H)
1704 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
y l]amino) cyclohexy I)-N'-[ 1 -(1 -naphthyl)ethyl]urea 487 (M + H) 1
1705 methyl N-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)amino]carbonyl}-
phenylalaninate 495 (M + H) 3
1706 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino) cyC1-5hexyl)-N'-( 1 -pheny lethyl)urea 437 (M + H) 3
1707 I-[4-(4-DimethyIamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-
cyclohexyl]-3-f 1 -pheny l-ethyl)-urea 437 (M + H)
1708 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yI]amino}cyclohexyI)-N'-{2,3^,6-tetrachlorophenyl)urea 545 (M + H) 3
1709 N-(2,4-dibromophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6?7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea 565 (M + H) 2
1710 N-(2,4-dichlorobenzyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)urea 491 (M + H) 2
1711 N-(2,4-dimethoxyphenyl)-N'-(cis-4-{[4-tdimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea 469 (M + H) 2
1712 N"(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamtno}cyclohexyi)-Nf-(2-ethoxyphenyl)urea 453 (M + H) 2
1713 N-(cis-4- {[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyC1-5hexyl)-N'-(2-fluorobenzyl)urea 441 (M + H) 2
1714 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyC1-5hexyl)-N'-(2-methyl-4-nitrophenyl)urea 468 (M + H) 3

449

Ex. No. compound name MS class
1715 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquina2olin-2-
yl]amino}cyclohexyl)-N'-(2-methyI-5-nitrophenvl)urea 468 (M + H)
1716 N-{cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino)cyclohexvI)-N'-(2-methylbenzyl)urea 437 (M + H)
1717 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)-N'-(2-nitrophenyl)urea 454 (M + H)
1718 N-l;3-benzodioxol-5-yl-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea 453 (M + H) -t
1719 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yllamino}cyclohexvl)-N'-(3,4,5-trimethoxyphenyl)urea 499 (M + H) 1
1720 N-(3,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)urea 469 (M + H) 2
1721 N-(3-chloro-4-methoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino}cyclohexYl)urea 473 (M + H) 3
1722 N-[4-bromo-2-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazolin-2-yllamino}cyclohexyl)urea 555 (M + H) ■>
1723 N-(4-bromobenzyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yIlamino}cyclohexyl)urea 501 (M + H) 3
1724 N-(4-chloro-2-methylphenyI)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazoIin-2-yllamino} eye lohexyl)urea 457 (M + H) 2
1725 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(4-fluorobenzyl)urea 441 (M + H) 2
1726 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-(4-methoxy-2-methylphenyl)urea 453 (M + H) 2
1727 N-(5-chloro-2,4-dimethoxyphenyI)-N'-(cis-4-{[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazolin-2-yIlamino}cyC1-5hexyl)urea 503 (M + H) 1
1728 N-[ 1 -(4-bromophenyl)ethyI]-N'-(cis-4- {[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino}cyclohexyl)urea 515 (M + H) 2
1729 N-(4-bromo-2-methylphenyl)-N'-(cis-4- {[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-y1]amino}cyclohexyl)urea 501 (M + H) 2
1730 ethyl N-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)amino]carbonyl}-
phenylalaninate 509 (M + H)
1731 N-(2,3-dihydro-l?4-benzodioxin-6-yI)-N'-(cis-4-{[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyC1-5hexyI)urea 467 (M + H) 3
1732 N-(2,6-dibromo-4-isopropy Iphenyl)-N'-(cis-4- {[4-(dimethy 1-
amino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea 607 (M + H) 3
1733 N-[3-(cyclopentyloxy)-4-methoxyphenyl]-N'-(cis-4-{[4-
(dimethylamino)-5,6,7;r8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)urea 523 (M + H) 3
1734 N-(3,4-dihydro-2H-l,5-benzodioxepin-7-yl)-N'-(cis-4-{[4-
(dimethylamino)-5,6,7T8-tetrahydroquinazolin-2-
yllamino)cyclohexyl)urea 481 (M + H) J
1735 N-(4-butyl-2-methyIphenyI)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazoIin-2-ynamino}cyC1-5hexyl)urea 479 (M + H) ->
1736 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-Nt-(5-methyl-3-phenylisoxazoI-4-yl)urea 490 (M + H) 1

450

Ex. No. compound name MS class
1737 N^-bromophenyO-N'-tcis^-l^-fdimethylaminoJ-S^J^-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea 503 (M + H)
1738 N-t4-cyanophenyl)-N'-(cis-4-{[4-{dimethylamino>5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea 450 (M + H) ■I
1739 N-(2,4-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea 493 (M + H)
1740 N-(2,4-dimethoxyphenyi)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea 485 (M + H) 1
1741 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexyl)-N'-(2,6-dimethylphenyi)thiourea 453 (M + H) ■->
1742 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-Nr-(2-ethyl-6-isopropylphenyl)thiourea 495 (M + H)
1743 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyl)-N'-(2-methoxyphenyl)thiourea 455 (M + H) 3
1744 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-l-naphthylthiourea 475 (M + H) 3
1745 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
vl]amino}cyclohexyl)-N'-(3,4,5-trimethoxyphenyl)thiourea 515 (M + H) 1
1746 N-(3,4-dimethoxyphenyl>N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)thiourea 485 (M + H) 1
1747 N-[4-(dimethy lamino)-1 -naphthy!]-N'-(cis-4- {[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)-
thiourea 518 (M + H) 2
1748 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
vllamino)cyC1-5hexyl)-N'-(2-ethylphenvl)thiourea 453 (M + H) 3
1749 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
vllamino}cvclohexyl)-N'-(2-methoxy-4-nitrophenyl)thiourea 500 (M + H)
1750 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
vl]amino}cyC1-5hexyl)-N'-(2-methoxy-5-methylphenyl)thiourea 469 (M + H) 2
1751 N-(4-bromo-2-chIoropheny l)-N'-(cis-4- {[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino}cyclohexyI)thiourea 537 (M + H) 1
1752 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cvclohexyl)-N'-(4-iodophenyl)thiourea 551 (M + H) 2
1753 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
vllamino)cyclohexyl)-N'-(2,4,6-tribromophenyl)thiourea 658 (M + H) 1
1754 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyI)-N'-(2,4,6-trichlorophenyI)thiourea 527 (M + H) 2
1755 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-mesitylthiourea 467 (M + H) 1
1756 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cvclohexyl)-N'-(2,4-dimethylphenyl)thiourea 453 (M + H) 2
1757 N-(2.6-diethyIphenyl)-N'-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-y!]amino}cyclohexyl)thiourea 481 (M + H) 1
3758 N-(2'bromo-4-methyIphenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-ynamino)cyclohexyl)thiourea 517 (M + H)
1759 N-(2'Ch]orobenzyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI"|amino}cyclohexyl)thiourea 473 (M + H)

451

Ex. No. compound name MS class
1760 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexylVN'-(2-ethyl-6-methvIphenvl)thiourea 467 (M + H)
1761 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyC1-5hexyI)-N'-(2-isopropylphenyl)thiourea 467 (M + H) ->
1762 methyl 3-({[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)amino]carbonothioyl}amino)-
benzoate 483 (M + H)
1763 N-(4-bromo2,6-dimethy lphenyl)-N'-(cis-4- {[4-(dimethy lamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyI)thiourea 531 (M + H) 1
1764 N-(4-bromo-2-methylphenyl)-N'-(cis-4-{[4-(dimethyIamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea 517 (M + H) 1
1765 N-[4-bromo-2-(trifluoromethyI)phenyl]-N'-(cis-4-{[4"(dimethyi-
amino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)-
thiourea 571 (M + H) 1
1766 N-(4-chloro-2-methylphenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino}cyclohexyl)thiourea 473 (M + H) 1
1767 N-(cis-4-{[4-{dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexvl)-N'-(l-naphthylmethyl)thiourea 489 (M + H)
1768 N-(2,3-dimethoxybenzyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)thiourea 499 (M + H) 3
1769 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)-N'-(2,4,5-trimethylphenyl)thiourea 467 (M + H) -t
1770 N-biphenyl-2-yl-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)thiourea 501 (M + H) -i
1771 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexvl)-N'-f2-methyI-4-nitrophenyl)thiourea 482 (M - H) -1772 N-(3-chlorobenzyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)thiourea 473 (M + H) 3
1773 ethyl 3-({[(cis-4-{[4-(dimethylamino)-5>6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)amino]carbonothioyl}amino)-
benzoate 497 (M + H) 3
1774 N-[4-chloro-2-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazoIin-2-yI]amino}cyclohexyl)-
thiourea 527 (M + H) 2
1775 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-Nr-(4-fluoro-2-methylphenyl)thiourea 457 (M + H) 2
1776 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexvl)-N'-(4-methoxy-2-methylphenyl)thiourea 469 (M + H) 2
1777 N-(5-chloro-2,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)-
thiourea 519 (M + H) 1
1778 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
vnamino}cyc!ohexyl)-N'-r(lR)-l-phenylethyIlthiourea 453 (M + H)
1779 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino)cyclohexyI)-N'-(2,3-dimethylphenyl)thiourea 453 (M + H)
1780 N-(2,4-dibromo-6-fluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yI]amino}cyclohexyl)thiourea 599 (M + H) 2

452

Ex. No. compound name MS class
1781 N-(2,4-dichloro-6-methylphenyI)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazoIin-2-vllamino}cyclohexv0thiourea 507 (M + H) 1
1782 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y!lamino}cyclohexyl)-N'-(2-ethoxyphenyl)thiourea 469 (M + H) 2
1783 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cvclohexyI)-N'-(2-isopropyl-6-methyIphenyl)thiourea 481 (M + H)
1784 N-(2,3-dihydro-I,4-benzodioxin-6-yl)-N'-(cis-4-{[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)-
thiourea 483 (M + H)
1785 N-1,3-benzodioxoI-5-yl-N'-(cis-4- {[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yf]amino}cyclohexyi)thiourea 469 (M + H)
1786 N-(3-chloro-2-methyIphenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6.7,8-tetrahydroquinazoiin-2-yl]amino}cyC1-5hexyl)thiourea 473 (M + H)
1787 N-[4-bromo-2-(trifluoromethoxy)phenyl]-N'-(cis-4-{[4-
(dimethyl-amino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-thiourea 587 (M + H) 2
1788 N-(4-chIoro-2,5-dimethoxyphenyI)-N'-(cis-4-{[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)-
thiourea 519 (M + H) 2
1789 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)-N'-(5-methyl-3-phenylisoxazol-4-yl)-
thiourea 506 (M + H)
1790 l-BicyC1-5[2.2.1]hept-2-yl-3-[4-(4-dimethylamino-5,6,7,8-
tetrahydro-quinazolin-2-ylamino)-cyclohexyIl-thiourea 443 (M + H)
1791 methyl 3-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazoIin-2-yl]amino}cyclohexyl)amino]carbonothioyl}araino)-
4-methylthiophene-2-carboxylate 503 (M + H)
1792 methyl 3-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yI]amino}cyclohexyl)amino]carbonothioyl}amino)-
thiophene-2-carboxylate 489 (M + H)
1793 N-(4-butyI-2-methylphenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazoiin-2-y!]amino}cyclohexyl)thiourea 495 (M + H) 3
1794 N-(3,5-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino>5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cvclohexvI)urea 477 (M + H) 3
1795 N-(2?3-dichlorophenyI)-Nf-{cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazoIin-2-yllamino}cyclohexy!)urea 477 (M + H) 2
1796 N-(cis-4-{[4-(dimethy!amino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(4-methy]phenyI)urea 423 (M + H) 2
1797 N-(256-diisopropyIphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7!8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea 493 (M + H) 2
1798 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexvl)-N'-f2,3-dimethyl-6-nitrophenyl)urea 482 (M + H) 3
1799 N-(2,6-dibromo-4-fluorophenyI)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino)cyC1-5hexyl)urea 583 (M + H) 3
1800 N-(2,6-dtchlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyI)urea 477 (M + H) 3
1801 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ylIamino}cyc]ohexy])-N'-(2-methoxy-5-niethylphenyI)urea 453 (M + H) 3

453

Ex. No. compound name MS class
1802 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
Yllamino)cyclohexyl)-N'-(2-methyl-6-nitrophenyl)urea 468 (M + H) ■>
1803 N-(3,4-difIuorophenyl>N'-(cis-4-{[4-(dimethylamino>5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)urea 445 (M + H) 3
1804 N-(3,5'difluorophenyl)-N'-tcis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea 445 (M + H) ">
1805 N-(3-chloro-4-fluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazoIin-2-yllamino}cyclohexyl)urea 461 (M + H)
1806 N-(3-acetylphenyl)-N'-(cis-4-{[4-(dimethylamino)-5;6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)urea 451 (M + H)
1807 N-l-adamantyl-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-vnamino}cyclohexyl)urea 467 (M + H) 3
1808 N-(4-acetylphenyl>N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyI)urea 451 (M + H) *■»
1809 N-{[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
y Hamino} cyclohexyl)aminolcarbonyl} benzamide 437 (M + H)
1810 N-(tert-butyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)urea 389 (M + H) 3
1811 N-[3,5-bis(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazolin-2-yllamino}cyC1-5hexvl)urea 545 (M + H) 3
1812 N-benzyl-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroq uinazol in-2 -y 1] am i n o } eye lohexy l)urea 423 (M + H) 3
1813 N-(4-bromophenyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea 487 (M + H)
1814 N-(3-chlorophenyl)-N'-(cis-4- {[4-(dimethylamino)-5,6,7,8-
tetrahvdroquinazoIin-2-yl]amino}cyclohexyl)urea 443 (M + H) -1815 N-(4-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)urea 443 (M + H) ■>
1816 N-cyC1-5hexyl-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)urea 415 (M + H) -1817 N-(3-cyanophenyl)-N'-(cis-4-{[4-(dimethylamino)-5;6,7,8-
tetrahydroquinazolin-2-vllamino}cyclohexyl)urea 434 (M + H) -i
1818 N-(3,4-dichIorophenyl)-Nt-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazoIin-2-y{lamino)cyclohexyl)urea 477 (M + H) 3
1819 N-(2,4-dichlorophenyI)-N'-(cis-4-{[4-(dimethy]amino)-5,6,7,8-
tetrahvdroquinazolin-2-yl]amino}cyclohexyl)urea 477 (M + H)
1820 N-(2,6-difIuorophenyl)-N'-(cis-4-{[4-(dimethyiamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)urea 445 (M + H) 3
1821 N-(2,5-dichlorophenyI)-Nr-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-ynamino}cyclohexyl)urea 477 (M + H) 3
1822 ethyl N-{[(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydro-
quinazoIin-2-yIlamino}cyC1-5hexyl)aminolcarbonyl}^lvcinate 419 (M + H) 3
1823 ethyl 4-({[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyc1ohexyl)amino]carbonyl}amino)-
benzoate 481 (M + H) 3
1824 N-(cis-4-{[4-(dimethy]amino)-5,6,7,8-tetrahydroquinazolin-2-
Yl]amino)cyclohexy!)-N'-t4-ethylphenyl)urea 437 (M + H) 3

454

Ex. No. compound name MS class
1825 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yilamino}cyclohexyI)-N'-ethylurea 361 (M + H) 3
1826 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyI>N'-f4-fluoro-3-nitrophenyl)urea 472 (M + H) 3
1827 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-(3-fiuorophenyl)urea 427 (M + H) 3
1828 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)-N'-(2-fluorophenyI)urea 427 (M + H)
1829 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)-N'-(4-isopropylphenyl)urea 451 (M + H) "J
1830 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)-N'-isopropy]urea 375 (M + H) 3
1831 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyc]ohexyl)-Nr-(4-methoxyphenyI)urea 439 (M + H)
1832 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cvclohexyl)-N'-(4-methyl-2-nitrophenvl)urea 468 (M + H) 3
1833 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yllamino}cyclohexyl)-N'-(2-methoxyphenyl)urea 439 (M + H) ■~i
1834 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyI)-N'-(3-methoxyphenyl)urea 439 (M + H) 3
1835 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexyl)-N'-(4-methoxybenzyl)urea 453 (M + H)
1836 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(3-methylbenzyl)urea 437 (M + H) 3
1837 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexvI)-N'-propylurea 375 (M + H) 3
1838 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y!lamino)cyC1-5hexyl)-N'-[3-(trifluoromethyl)phenyilurea 477 (M + H)
1839 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino)cyC1-5hexyl)-N'-13-ftriethoxysilyl)propyllurea 537 (M + H) 3
1840 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllaminolcyclohexylVN'-fS-methylphenyOurea 423 (M + H) 3
1841 N-(3-chloro-4-methylphenyl)-N'-(cis-4-{[4-(dimethyIamino)-
5,6,7,8-tetrahydroquinazoIm-2-yl]amino)cyclohexy!)urea 457 (M + H) 3
1842 l-[4-(4-Dimethyiamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-
cyclohexy I]-3-( 1 -naphthalen-1 -y I-ethyl)-urea 487 (M + H)
1843 N-[2-(difluoromethoxy)phenyl]-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyI)urea 475 (M + H)
1844 methyl 2-({[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydro-
quinazoiin-2-yl]amino}cyclohexyl)amino]carbonyl}amino)-
benzoate 467 (M + H)
1845 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyC1-5hexyl)-N'-f2-{methylthio)phenyllurea 455 (M + H) 3
1846 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino)cyclohexyI)-N'-{2,4,5-trichlorophenyl)urea 511(M + H) 2
1847 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexyl)-N'-(2,4-dimethyIphenyl)urea 437 (M + H) 3

455

Ex. No. compound name MS class
1848 N-(2,5-difluorophenyl)-N'-(cis-4-{[4-(dimethyiamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)urea 445 (M + H)
1849 N-(2,5-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahvdroquinazolin-2-yl]amino}cyclohexyl)urea 469 (M + H) 2
1850 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-(2,5-dimethyIphenvl)urea 437 (M + H) ->
J
1851 N-(2-benzylphenyl)-N'-(cis-4- {[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazoIin-2-yllamino}cyc!ohexyl)urea 499 (M + H)
1852 N-(2-bromo-4,6-difluorophenyl)-N'-(cis-4- {[4-(dimethy lamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyC1-5hexyI)urea 523 (M + H)
1853 N-[2-chIoro-4-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-tdimethyl-
amino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)-
urea 511 (M + H) 3
1854 N-(2-chIoro-4-nitrophenyl)-N'-(cis-4-{[4-(dimethyIamino)-
5,6,7,8-tetrahydroquinazolin-2-yIlamino}cyC1-5hexyl)urea 488 (M + H)
1855 N-[2-chIoro-5-(trifluoromethyl)phenyi]-N'-(cis-4-{[4-(dimethyI-
amino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)-
urea 511 (M + H)
1856 N-(2-chloro-5-methylphenyl)-N'-(cis-4- {[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cvclohexyl)urea 457 (M + H)
1857 ethyl 2-({[(cis-4-{[4-(dimethylamin o)-5,6,7,8-tetrahydro-
quinazolin-2-yI]amino}cyclohexyl)amino]carbonyl}arnino)-
benzoate 481 (M + H)
1858 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)-N'-[2-fluoro-3-(trifluoromethyl)phenyl]-
urea 495 (M + H)
1859 N-(cis-4- {[4-(dimethylamino)-5;6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-[2-fluoro-5-(trifluoromethyl)phenylj-
urea 495 (M + H) 3
1860 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-(2-fluoro-5-methylphenvl)urea 441 (M + H) J
1861 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)-N'-(2-methoxy-4-nitrophenyI)urea 484 (M + H) 3
1862 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino)cyclohexyl)-N'-f2-methoxy-5-nitrophenyl)urea 484 (M + H)
1863 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]aminolcyclohexy])-N'-2-naphthylurea 459 (M + H)
1864 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino)cyclohexyl)-N'-(2-phenoxyphenyl)urea 501 (M + H) 3
1865 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexyl)-N'-[3-(methy!thio)phenyl]urea 455 (M + H) 3
1866 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-Nf-{3-f(trifluoromethyl)thiolphenyl}urea 509 (M + H) 'i
1867 N-(3,4-dichlorobenzyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-ynamino}cyclohexyI)urea 491 (M + H)
1868 N-(3,5-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yilamino}cyclohexy!)urea 469 (M + H) 3

456

Ex. No. compound name MS class
1869 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(3,5-dimethylphenyl)urea 437 (M + H) 3
1870 methyl 3-{{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-y!]amino}cyclohexyl)amino]carbonyl}amino)-
benzoate 467 (M + H) ■>
1871 N-(cis-4-{[4-fdimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(3-ethylphenyl)urea 437 (M + H)
1872 N-(cis-4-{[4-(dimethylamino)-5!6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)-N'-[3-fluoro-5-(trifluoromethyl)phenyI]-
urea 495 (M + H) 3
1873 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y]lamino}cyclohexyl)-N'-(3-fkiorobenzy])urea 441 (M + H)
1874 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexyl)-N'-(3-nitrophenvl)urea 454 (M + H) 3
1875 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino)cyclohexyl)-N'-(3-phenoxyphenyl)urea 501 (M + H)
1876 N-[4-(difluoromethoxy)phenyl]-N'-(cis-4- {[4-(dimethy lamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino}cyclohexyl)urea 475 (M + H) 3
1877 butyl 4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazoIin-2-yl]amino}cyclohexyl)amino]carbonyl}amino)-
benzoate 509 (M + H) 3
1878 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-Nl-f4-(trifluoromethyl)phenyl]urea 477 (M + H) J
1879 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-{4-f(trifluoromethyl)thiolphenyl}urea 509 (M + H) ■->
1880 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazo]in-2-
yllamino}cyC1-5hexyl)-N'-(4,5-dimethyl-2-nitrophenyl)urea 482 (M + H)
1881 N-[4-(benzyloxy)phenyl] -N'-(cis-4-{ [4-(dimethyl am ino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea 515 (M + H)
1882 N-(4-benzylphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yIlamino}cyclohexyl)urea 499 (M + H)
1883 N-(4-bromo-2-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazoIin-2-yllamino}cyclohexyl)urea 521 (M + H) 2
1884 N-(4-bromo-2-fluorophenyI)-N'-(cis-4-{[4-(dimethyIamino)-
5,6,7,8-tetrahydroquinazolin-2-yI]amino}cyclohexyl)urea 505 (M + H)
1885 N-(4-bromo-3-methylphenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino}cyclohexyl)urea 501 (M + H)
1886 N-(4-chloro-2-nitrophenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazoIin-2-yllamino}cyclohexyl)urea 488 (M + H) 3
1887 N-[4-chloro-3-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethyl-
amino>5,6,7,8-tetrahydroquinazolin-2-Ynaminolcyclohexyl)urea 511 (M + H)
1888 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexyI)-N'-(4-ethoxyphenyl)urea 453 (M + H) i
1889 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-(4-fluoro-2-nitrophenyl)urea 472 (M + H) *■>
1890 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyI)-N'-[4-fluoro-3-(trifIuoromethyl)phenyl]-
urea 495 (M + H) 3

457

Ex. No. compound name MS class
1891 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cvclohexyl)-N'-f4-(heptyloxy)phenyl]urea 523 (M + H) "»
1892 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)-N'-(4-iodophenyl)urea 535 (M + H) *■>
1893 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-
yI]amino}cyC1-5hexyl)-N'-(4-methoxy-2-nitrophenyi)urea 484 (M + H) 3
1894 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(4-methyI-3-nitrophenyl)urea 468 (M + H) -i
1895 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyI)-N'-(4-methyibenzyI)urea 437 (M + H) J
1896 N-(4-butoxyphenyl>N'-(cis-4-{[4-(dimethylamino)-5,6,7!8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea 481 (M + H) -i
1897 N-(4-butylphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyI)urea 465 (M + H)
1898 N-biphenyl-4-yl-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)urea 485 (M + H) 3
1899 N-(5-chloro-2-methoxyphenyI)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea 473 (M + H) •>
1900 N-(5-chloro-2-methylphenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea 457 (M + H) 3
1901 N-(5-chloro-2-nitrophenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino}cyclohexyI)urea 488 (M + H) 3
1902 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(5-fluoro-2-methylphenyl)urea 441 (M + H) 3
1903 N-(2,3-dihydro-1 H-inden-5-yl)-N'-(cis-4-{ [4-(dimethy lamino)-
5,6,7,8-tetrahydroquinazoIin-2-yl]amino)cyC1-5hexyl)urea 449 (M + H) 3
1904 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyi)-N'-9H-fluoren-2-ylurea 497 (M + H) 3
1905 N-(cis-4-{[4-(dimethylamino)-5,6?7J8-tetrahydroquinazolin-2-
y]lamino}cyclohexyl)-N'-9H-fluoren-9-ylurea 497 (M + H)
1906 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexvl)-N'-(2-phenylethyl)urea 437 (M + H) 3
1907 N-cyclopentyl-NI-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amtno}cyC1-5hexyl)urea 401 (M + H) 3
1908 methyl 4-({[(cis-4-{[4-(dimethyiamino>5,6,7>8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)amino]carbonyl}amino)-
benzoate 467 (M + H) 3
1909 N-(cis-4-{[4-(dimethylamino)-5,6J7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)-N'-f2-(trifIuoromethoxy)phenyl]urea 493 (M + H) 2
1910 butyl 2-({[(cis-4-{[4-(dimethyIamino)-5!6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)amino]carbonyl}amino)-
benzoate 509 (M + H) J
1911 dimethyl 5-{ {[(cis-4-{ [4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyI)amino]carbonyl}amino)-
isophthalate 525 (M + H) 3
1912 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino)cyclohexyl)-N'-r4-ftrifluoromethoxy)phenyI]urea 493 (M + H)

458

Ex. No. compound name MS class
1913 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(2,2,4,4-tetrafluoro-4H-l,3-
benzodioxin-6-yI)urea 539 (M + H)
1914 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyI)-N'-[2-(2-thienyl)ethyllurea 443 (M + H) 3
1915 N-(2-cyanophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea 434 (M + H) 3
1916 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino)cyC1-5hexyi)-N'-2-thienylurea 415 (M + H)
1917 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyC1-5hexyl)-N'-3-thienvlurea 415 (M + H)
1918 N-(4-terl-butylphenyl)-N'-(cis-4-{[4-(dimethylamino>5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)urea 465 (M + H) 3
1919 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cvclohexyl)-N'-(5-phenvl-2-thienyl)urea 491 (M + H) 3
1920 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyC1-5hexy!)-N'-(6-fluoro-4H-l,3-benzodioxin-8-yl)urea 485 (M + H)
1921 benzyl 4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro
quinazolin-2-yI]amino}cyclohexyl)amino]carbonyl}amino)-
piperidine-1-carboxylate 550 (M + H) 3
1922 N-[4-(dimethylamino)phenyl]-N'-(cis-4- {[4-(dimethyl amino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyC1-5bexyl)urea 452 (M + H) 3
1923 N-(2,6-dichIoropyridin-4-yl)-NI-(cis-4-{[4-tdimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino}cyclohexyI)urea 478 (M + H)
1924 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y!lamino}cyC1-5hexyI)-N'-(3,5-dimethvlisoxazol-4-yl)urea 428 (M + H) 3
1925 N-(3-acetyIphenyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cvclohexyl)thiourea 467 (M + H) 3
1926 N-(4-acetylphenyI)-Nt-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexy])thiourea 465 (M - H) 3
1927 N-[3,5-bis(trifluoromethyl)phenyl]-N1-(cis-4-{[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)-
thiourea 561 (M + H)
1928 N-benzyl-Nf-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)thiourea 439 (M + H) 3
1929 N-(3-bromophenyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyI)thiourea 503 (M + H) 3
1930 N-butyl-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)thiourea 405 (M + H) 3
1931 N-cyC1-5hexyl-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)thiourea 431 (M + H) 3
1932 N-cyclopentyI-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoUn-2-yIlamino}cyclohexyl)thiourea 417 (M + H) 3
1933 N-(3-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)thiourea 459 (M + H) 3
1934 N-(4-ch!orophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazo!in-2-yl]amino}cyclohexyl)thiourea 459 (M + H)

459

Ex. No. compound name MS class
1935 N-(2,5-difluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexy!)thiourea 461 (M + H) J
1936 N-(2,5-dichlorophenyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)thiourea 493 (M + H) 1
1937 N-(3,4-dichlorophenyI>N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoiin-2-yl]amino}cyclohexyl)thiourea 493 (M + H)
1938 N-(2,6-dichlorophenyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyI)thiourea 493 (M + H)
1939 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)-N'-(4-ethoxyphenyl)thiourea 469 (M + H)
1940 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino)cyclohexyl)-N'-(2-furylmethyI)thiourea 429 (M + H)
1941 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexy])-N'-(4-fluorophenyl)thiourea 443 (M + H)
1942 N-(cis-4-{[4-(dimethylamino)-556,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-hexylthiourea 433 (M + H)
1943 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-[4-(trans^-propylcyclohexyI)phenyl]-
thiourea 549 (M + H) -t
1944 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexyI)-N'-isobutylthiourea 405 (M + H) ->
1945 N-(cis-4-{[4-(dimethylamino)-5,6,758-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)-N'-(4-methoxybiphenyl-3-yl)thiourea 531 (M + H)
1946 N-(l,3-benzodioxol-5-ylmethyI)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-vl]amino}cyclohexyl)thiourea 483 (M + H) 3
1947 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cvclohexyI)-N'-(3-methylphenyl)thiourea 439 (M + H)
1948 N-(cis-4~{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexyI)-N'-["4-(methylthio)phenvllthiourea 471 (M + H) 3
1949 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(4-methoxyphenyl)thiourea 453 (M - H) 3
1950 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyC1-5hexyl)-N'-(2-methylprop-2-en-l-vI)thiourea 403 (M + H) ->
1951 N-(cis-4-{[4-(dimethylamino)-5,6,7>8-tetrahydroquinazolin-2-
yllamino}cyclohexyI)-N'-methyIthiourea 363 (M + H) ->
1952 N-(cis-4-{[4-(dimethy!amino)-5!6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)-N'-(3-nitrophenvl)thiourea 470 (M + H) ->
1953 N-(cis-4-{[4-(dimethylamino)-5,6,7,84etrahydroquinazolin-2-
yllamino}cyclohexy])-N'-(4-nitrophenyl)thiourea 470 (M + H)
1954 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexylVN'-(l,l,33-tetramethylbutYl)thiourea 461 (M + H) 3
1955 N-tcis-4-{[4-(dimethyIamino)~5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)-N'-pheny!thiourea 425 (M + H)
1956 N-(cis-4-{[4-(dirnethyIamino>5,6,7,8-tetrahydroquinazoIin-2-
yIlamino}cyclohexyI)-Nf-propyIthiourea 391 (M + H)
1957 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-f3-(trifluoromethyl)phenyl]thiourea 493 (M + H) 3

460

Ex. No. compound name MS class
1958 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
Vl]amino}cyclohexyl)-N'-(tetrahvdrofuran-2-ylmethyl)thiourea 433 (M + H)
1959 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(4-methylphenyl)thiourea 439 (M + H) 3
1960 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)-N'-(2-methylphenyI)thiourea 439 (M + H) 3
1961 N-(tert-butyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino|cyclohexyl)thiourea 405 (M + H) -i
J
1962 N-l-adamantyl-N'-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea 483 (M + H)
1963 N-(2-bromophenyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroqufnazolin-2-ynamino}cyclohexyl)thiourea 503 (M + H) ->
J
1964 N-(2-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-ynamino}cyclohexyl)thiourea 459 (M + H) 3
1965 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexvI)-N'-(2-phenylethyl)thiourea 453 (M + H) 3
1966 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cYclohexvl)-N'-(4-ethylphenYl)thiourea 453 (M + H) 3
1967 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyC1-5hexyl)-N'-[2-(methylthio)phenynthiourea 471 (M + H)
1968 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroqiiiriazolin-2-
yl]amino}cvclohexyl)-N'-|'2-(trifluoromethoxy)phenyllthiourea 509 (M + H) 3
1969 N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)-N'-[2-(trifluoromethyl)phenyllthiourea 493 (M + H) 3
1970 N-(cis^-{[4-(dimetbylamino)-5,6,7,8-tetrahydroqumazolin-2-
yl]amino}cyclohexyl)-N'-(2,3,4-trifluorophenyl)thiourea 479 (M + H) 3
1971 N-(2,3-dichIorophenyl)-N'-(cis-4-{[4-(dimethylamino>5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea 493 (M + H) J
1972 N-(2,4-difluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea 461 (M + H)
1973 N-(2,5-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethy]amino)-5,6,7,8-
tetrahydroquinazolin-2-yIlamino}cyclohexyl)thiourea 485 (M + H)
1974 N-(2,6-difluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)thiourea 461 (M + H) 3
1975 N-(2-chloro-4-nitrophenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-vnamino}cyclohexyl)thiourea 504 (M + H)
1976 N-[2-(difluoromethoxy)phenyl]-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-Yl]amino]cyclohexyl)thiourea 491 (M + H)
1977 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)-N'-[2-fluoro-5-(trifluoromethyl)phenyl]-
thiourea 511 (M + H) 3
1978 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexy!)-N'-(2-fluorophenyl)thiourea 443 (M + H) i
1979 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-(2-iodophenyI)thiourea 551 (M + H)
1980 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yljamino} cyc!ohexyI)-N'- {3-[{trifluoromethyl)thio]phenyl} -
thiourea 525 (M + H)

461

Ex. No. compound name MS class
1981 N-(3,5-dichlorophenyl)-N'-(cis-4-{[4-(dimethyiamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyI)thiourea 493 (M + H) -*>
1982 N-(3,5-difIuorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)thiourea 461 (M + H)
1983 N-(3-cyanophenyi)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazo!in-2-yl]amino}cyclohexy!)thiourea 450 (M + H)
1984 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)-N'-(3-fluorophenyl)thiourea 443 (M + H) 3
1985 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(3-iodophenyI)thiourea 551 (M + H) J
1986 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-(3-methoxyphenyl)thiourea 455 (M + H) *■>
1987 N-[4-(difluoromethoxy)phenyl]-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexvl)thiourea 491 (M + H) ->
1988 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexyl)-N'-[4-(trifluoromethoxy)phenyllthiourea 509 (M + H) j
1989 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cvclohexyl)-N'-[4-(trifIuoromethyl)phenyllthiourea 493 (M + H) 3
1990 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-{4-[(trifluoromethyl)thio]phenyl}-
thiourea 525 (M + H)
1991 N-(4-bromo-2-fluorophenyl)-N'-(cis-4- {[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino}cyclohexyl)thiourea 520 (M)
1992 N-[4-chloro-3-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}cyclohexyl)-
thiourea 527 (M + H)
1993 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)'N'-[4-fluoro-3-(trifluoromethyl)phenyl]-
thiourea 511 (M + H) i
1994 N-(5-chioro-2-methylphenyl)-Nt-(cis-4-{[4-(dimethyIamino)-
5,6,7,8-tetrahydroquinazolin-2-y!lamino}cyclohexyl)thiourea 473 (M + H) -*>
1995 N-bicyclo[2.2.1]hept-2-yl-N'-(cis-4-{[4-{dimethylamino)-5,6,7s8-
tetrahydroquinazoIin-2-yl]amino}cyC1-5hexyl)thiourea 443 (M + H) 3
1996 tert-butyl [4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)amino]carbonothioyl}amino)-
phenyll carbarn ate 540 (M + H) 3
1997 N-[2-(3,4-dimethoxyphenyl)ethyl]-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazoIin-2-yl]amino}cyclohexyl)thiourea 513 (M + H)
1998 N-[2-(4-chlorophenyl)ethyl]-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yI]amino}cyclohexyl)thiourea 487 (M + H)
1999 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyI)-N'-(2,3,4,5-tetrachloropheny])thiourea 561 (M + H) 3
2000 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(2,4,5-trichlorophenyl)thiourea 527 (M + H)
2001 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y]]amino}cyclohexyl)-N'-(2,4,6-trifIuorophenyl)thiourea 479 (M + H) T
2002 N-(2,6-diisopropylphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)thiourea 509 (M + H)

462

Ex. No. compound name MS class
2003 N-[2-chIoro-5-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyI)-
thiourea 527 (M + H)
2004 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-f"3-(methylthio)phenyllthiourea 471 (M + H) j
2005 N-(3,4-dichlorobenzyl>N'-(cis-4-{[4-(dimethylamino>5,6,7,8-
tetrahydroquinazolin-2-yIlamino}cyclohexyl)thiourea 507 (M + H)
2006 N-(3,5-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea 485 (M + H) 1
2007 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)-N'-(3,5-dimethylphenyl)thiourea 453 (M + H)
2008 N-[3-(benzyloxy)phenyl]-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cvclohexy])thiourea 531 (M + H) 3
2009 3-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)amino]carbonothioyl}amino)benzoic acid 469 (M + H) 3
2010 N-(3-chloro-4-methylphenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino}cyclohexyl)thiourea 473 (M + H)
2011 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-(3-phenylpropyl)thiourea 467 (M + H) 3
2012 N-[4-(diethylamino)phenyl]-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyI)thiourea 496 (M + H)
2013 ethyl 4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yl]amino}cyclohexyl)amino]carbonothioyl}amino)-
benzoate 497 (M + H) -*
J
2014 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yllamino}cyclohexyl)-Np-ri-f4-fluorophenyl)ethyl]thiourea 471 (M + H)
2015 N-(cis-4-{[4-tdimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyI)-N'-(4-fluorobenzyl)thiourea 457 (M + H) 3
2016 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)-N'-(4-isopropylphenyl)thiourea 466 (M) -i
2017 N-(cis-4-{[4-(diraethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-N'-(4-methoxy-2-nitrophenyl)thiourea 500 (M + H) 3
2018 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yIlamino}cyclohexyl)-NL(4-methoxybenzyI)thiourea 469 (M + H) *>
2019 methyl 4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydro-
quinazolin-2-yI]amino}cyclohexyl)amino]carbonothioyl}amino)-
benzoate 483 (M + H) 3
2020 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yllamino}cyclohexyl)-N'-(4-methyl-2-nitrophenyl)thiourea 484 (M + H)
2021 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-(4-methyIbenzyl)thiourea 453 (M + H)
2022 N-(4-butylphenyt)-N'-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)thiourea 481 (M + H)
2023 N-(5-chIoro-2-methoxyphenyl)-N'-(cis-4-{[4-(dimethyIamino)-
5,6,7,8-tetrahydroquinazolin-2-ynamino)cyclohexyI)thiourea 489 (M + H)
2024 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)-N'-{l-phenylethyl)thiourea 453 (M + H) 3

46:

Ex. No. compound name MS class
2025 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexyl)-N'-(diphenyImethyI)thiourea 515 (M + H) ■>
2026 N-cyclododecyl-N'-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-y]]amino}cyclohexyl)thiourea 515 (M + H)
2027 N-(cyC1-5hexylmethyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-ynamino}cyclohexyl)thiourea 445 (M + H) 3
2028 N-cyclooctyI-N'-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea 459 (M + H) 3
2029 N-cyclopropyl-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yllamino}cyC1-5hexyl)thiourea 389 (M + H)
2030 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)-N'-(2,2-diphenyIethyI)thiourea 529 (M) 2
2031 N-(cis-4-{[4-(dimethy]amino)-5?6,7,8-tetrahydroquinazoIin-2-
yIlamino}cyC1-5hexvl)-N'-(2,3,5,6-tetrachlorophenyI)thiourea 561 (M + H) 3
2032 N-(2,4-dichlorobenzyI)-N'-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yIlamino}cyC1-5hexyl)thiourea 507 (M + H) 3
2033 N-(2,5-dibromophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yllamino}cyC1-5hexyl)thiourea 581 (M + H)
2034 N-[2-(2,5-dimethoxyphenyl)ethyl]-N'-(cis-4-{[4-(dimethylamino)-
5,6,7T8-tetrahydroquinazolin-2-yIlamino}cyC1-5hexyl)thiourea 513 (M + H) 3
2035 N-(2-chloro-5-nitrophenyl)-N'-(cis-4- {[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea 504 (M + H) 3
2036 N-(2-cyanophenyl)-NMcis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahvdroquinazolin-2-yllamino}cyclohexyl)thiourea 450 (M + H)
2037 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cvc!ohexvI)-N'-(2-fluorobenzyl)thiourea 457 (M + H) 3
2038 N-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
vI]amino}cyclohexyI)aminolcarbonothioyl}-2-furamide 443 (M + H) -i
2039 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
vIlamino}cyC1-5hexyl)-N'-(2-methoxy-5-nitrophenyl)thiourea 500 (M + H) 3
2040 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyl)-Nl-(2-methylbenzyI)thiourea 453 (M + H) 3
2041 N-(3,4-dimethoxybenzyl>N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)thiourea 499 (M + H) ■>
2042 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y!lamino}cyclohexyl)-N'-(3-ethyIphenyl)thiourea 453 (M + H) 3
2043 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllaminojcyC1-5hexyO-N'-fj-fJuorobenzyOthiourea 457 (M + H)
2044 N-(cts-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
vnamino}cyC1-5hexyl)-N'-(3-methoxybenzyI)thiourea 469 (M + H) 3
2045 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y]lamino}cyC1-5hexyl)-N'-(3-methylbenzyl)thiourea 453 (M + H) ->
2046 N-{4-bromo-3-chlorophenyI)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yI]amino}cyclohexvl)thiourea 537 (M + H) ->
2047 N-(4-bromo-3-methylphenyI)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yI]amino)cyC1-5hexyl)thiourea 517 (M + H) 3
2048 N-(4-decylphenyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquitiazoiin-2-yl]amino}cyclohexyI)thiourea 565 (M + H)

464

Ex. No. compound name MS class
2049 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-Nt-[4-(4-nitrophenoxv)phenyl]thiourea 562 (M + H) -»
2050 N-(cis-4-{[4-(dimethy]amino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyC1-5hexyl)-NT-{4-[f4-nitrophenyl)thio]pheny]}thiourea 578 (M + H)
2051 4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)amino]carbonothioyl}amino)-
benzenesulfonamide 502 (M -H) 3
2052 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino{cyclohexyl)-N'-[2-(4-methylphenyl)ethyl]thiourea 467 (M + H) 3
2053 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yllamino}cyclohexy!)-N'-(4-phenoxyphenyl)thiourea 517 (M + H)
2054 N-(2,3-dihydro-lH-inden-5-yl)-N'-(cis-4-{[4-(dimethyIamino)-
5,6.7.8-tetrahydroquinazolin-2-yllamino}cycfohexyl)thiourea 465 (M + H) 3
2055 N-cycloheptyl-N'-(cis-4-{[4-(dimethylamino>5,6,7,8-
tetrahydroqiunazoIin-2-yI]amino}cyclohexyl)thiourea 445 (M + H) 3
2056 N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-
y l]amino} cyclohexyl)-N'-prop-2-vn-1 -ylthiourea 387 (M + H) i
2057 N-(cis^-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyl)-N'-[4-(piperidin-l-yIsulfonyl)phenyl]-
thiourea 572 (M + H)
2058 N-{2-cyclohex-l-en-l-yIethyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino}cyclohexyl)thiourea 457 (M + H) ->
2059 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)-N'-(2,5-dimethylphenyl)thiourea 453 (M + H) 3
2060 N-(2-bromo-4-isopropylphenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino}cvclohexyl)thiourea 545 (M + H)
2061 N-(2-bromo-5-fluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea 521 (M + H) ->
2062 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yi]amino}cyclohexyl)-N'-(2-methoxybenzyl)thiourea 469 (M + H) 3
2063 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyC1-5hexyI)-N'-(3,4-dimethylphenyl)thiourea 453 (M + H) 3
2064 N-(cis^-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyI)-N'-(4-pbenylbutyl)thiourea 481 (M + H)
2065 N-(4-tert-butyIphenyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahvdroquinazolin-2-yI]amino}cyclohexyl)thiourea 481 (M + H) 3
2066 N-(5-chIoro-2-fluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazoIin-2-yllamino}cyclohexyl)thiourea 477 (M + H) 3
2067 N-bicyclo[2.2.1]hept-5-en-2-yl-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyclohexyI)thiourea 441 (M + H) 3
2068 N-{cyclopropyImethyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazo!in-2-yI]amino}cyclohexyI)thiourea 403 (M + H) -i
2069 ethyl 2-({[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydro-
quinazoIin-2-yI]amino}cyclohexyl)amino]carbonothioyl}amino)-
4,5,6,7-tetrahydro-l-benzothiophene-3-carboxylate 557 (M + H) i
2070 N-(2-bromo-4-fluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-
S f>7 8-tptrahvflrnniiina7nlin-'7-vtlaminolcvr.lnhexvl"lthiniirea 521 (M + H) 3

465

Ex. No. compound name MS class
2071 N-(3-chloro-4-fluorophenyl)-N'-(cis-4-{[4-(dimethyIamino)-
5,6,7,8-tetrahydroquinazolin-2-vIlamino}cyclohexyl)thiourea 477 (M + H) 3
2072 N-[4-(dimethylamino)phenyi]-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yl"|amino}cyclohexyl)thiourea 468 (M + H)
2073 N-[3-{diethylamino)propyI]-N'-(cis-4-{[4-(dimethyIamino)-
5,6,7,8-tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)thiourea 462 (M + H)
2074 N-(cis-4-{[4-(dimethyIamino)-5,6?7,8-tetrahydroquinazolin-2-
yI]amino)cyC1-5hexyl)-N'-(2-morpholin-4-ylethyl)thiourea 462 (M + H) 3
2075 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)-N'-(4-phenanthro[9,10-d][l,3]oxazol-2-
ylpheny!)thiourea 642 (M + H)
2076 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)-N'-pyridin-3-ylthiourea 426 (M + H)
2077 N-(4-{(E)-[4-(dimethylamino)phenyl]diazenyl}phenyl)-N'-(cis-4-
{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yllamino}cvclohexyl)thiourea 572 (M + H) 3
2078 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino}cyclohexyI)-Nl-(3-morphoIin-4-ylpropyI)thiourea 476 (M + H) 3
2079 N-(4-chlorobenzyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoiin-2-yI]amino}cvclohexyl)thiourea 473 (M + H) 3
2080 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cvclohexyI)-N'-{4-[(E)-phenyIdiazenyllphenyl}thiourea 529 (M + H) -i
2081 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)-N'-(2-piperidin-l-ylethvl)thiourea 460 (M + H) 3
2082 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)-N'-f4-(lH-pyrazol-l-yl)phenyl]thiourea 491 (M + H)
2083 N-2,l,3-benzothiadiazol-4-yI-N'-(cis-4-{[4-(dimethyIamino)-
5,6,7,8-tetrahydroquinazolin-2-ynamino}cyC1-5hexyl)thiourea 483 (M + H) 3
2084 N-2,l,3-benzothiadiazol-5-yl-N'-(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino}cyclohexyl)thiourea 483 (M + H) 3
2085 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyI)-N'-(3,5-dimethylisoxazol-4-yl)thiourea 444 (M + H)
2086 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI>N'-[4-(I,3-oxazol-5-yl)phenyl]thiourea 492 (M + H) *">
2087 N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-
yI]amino}cyC1-5hexyI)-N'-(6-morphoIin-4-yIpyridin-3-yl)thiourea 511 (M + H) 3
2088 N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyl)-N'-(6-phenoxypyridin-3-y])thiourea 518 (M + H)
2089 N-(2-chlorophenyI)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)urea 438 (M + H) 2
2090 N-(cis-4- {[4-(dimethy Iamino)quinolin-2-yi]amino} cyclohexyl)-
N'-(2,6-dimethylphenyt)urea 432 (M + H)
2091 N-(2,4-difluorophenyI)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)urea 440 (M + H) ^>
2092 N-(cis-4-{[4-(dimethylamino)qutnolin-2-yl]amino}cyclohexyl)-
N'-(2-ethyl-6-methylphenyl)urea 446 (M + H) 2
2093 ethyl N-{[(cis-4-{ [4-(dtmethylamino)quinoiin-2-
yl]amino}cyclohexyl)amtnolcarbonyi}leucinate 470 (M + H)

466

Ex. No. compound name MS class
2094 N-tcis-4-{[4-(dimethyIamino)quinoIin-2-yl]amino}cyC1-5hexyl)-
N'-(4-fluorophenyl)urea 422 (M + H)
2095 N-(cis-4-{[4-(dimethylamino)qLiinoIin-2-yl]amino}cyC1-5hexyl)-
N'-[4-(methylthio)phenyllurea 450 (M + H)
2096 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
N'-[2-(trifluoromethyI)phenyilurea 472 (M + H) 3
2097 N-(cis-4-{[4-(dimethy]amino)quinolin-2-yi]amino}cyclohexyI)-
N'-mesitylurea 446 (M + H) 1
2098 N-(cis-4-{[4-(dimethylamino)quino!in-2-yI]amino}cyclohexyI)-
N'-(2-methylphenyl)urea 418 (M + H) j
2099 N-(cis-4- {[4-(dimethyiamino)quinolin-2-yl]amino} cyclohexyl)-
N'-(2,4,6-trichlorophenyl)urea 506 (M + H) 2
2100 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-
N'-(2,4,6-tribromophenyl)urea 637 (M + H) 1
2101 N-(2,4-dibromo-6-fluorophenyl)-N'-(cis-4- {[4-
(dimethyIamino)quinoIin-2-yl]amino}cyclohexyl)urea 578 (M + H) 2
2102 N-(2,6-diethylphenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yl~lamino}cyclohexyl)urea 460 (M + H) 1
2103 N-[2-chloro-6-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-
(dimethylamino)quinolin-2-yl]amino}cyclohexyl)urea 506 (M + H) 3
2104 N-(2-chloro-6-methylphenyl)-N'-(cis-4-{[4-
(dimethylamino)quinolin-2-yllamino}cyclohexyl)urea 452 (M + H) 3
2105 N-(2-chloroben2yl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)urea 452 (M + H) 2
2106 N-(cis-4-{[4-(dimethylammo)quinoIin-2-yl]amino}cyclohexyl)-
N'-(2-ethyl-6-isopropylphenyl)urea 474 (M + H) 2
2107 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
N'-(2-ethylphenyl)urea 432 (M + H) 3
2108 N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyi)-
N'-(2-iodophenyi)urea 530 (M+H)
2109 N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexyl)-
N'-(2-isopropyI-6-methylphenyl)urea 460 (M + H) 2
2110 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-
N'-(2-isopropy!phenyl)urea 446 (M + H) 3
2111 N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-
N'-(2-methyl-3-nitrophenyl)urea 463 (M + H) 3
2112 N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-
N'-(2-propylphenyl)urea 446 (M + H)
2113 N-(2-tert-butyl-6-methylphenyl)-N'-(cis-4-{[4-
(dimethylamino)quinolin-2-yl]amino}cyclohexyl)iirea 474 (M + H) 1
2114 N-(2-tert-butylphenyI)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino j cyclohexyl)urea 460 (M + H)
2115 N-(3-chIoro-2-methyIphenyI)-N'-(cis-4-{[4-
(dimethylamino)quinolin-2-yllamino}cyclohexyI)urea 452 (M + H) 3
2116 N-(4-bromo-2,6-difluorophenyl)-N'-(cis-4- {[4-
(dimethylamino)quinoIin-2-yI]amino}cyC1-5hexyl)urea 518 (M + H)
2117 N-[4-chloro-2-(trifluoromethyI)phenyl]-N'-(cis-4-{[4-
(dimethylamino)quinolin-2-yI]amino}cyC1-5hexyl)urea 506 (M + H) 3

467

Ex. No. compound name MS class
2118 N-(4-cyanophenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino} cyclohexyl)urea 429 (M + H) 3
2119 N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyI)-
N'-(diphenyImethyl)urea 494 (M + H) 2
2120 N-(4-bromo-2,6-dimethylphenyl)-N'-(cis-4-{[4-
(dimethylamino)quinolin-2-ynamino}cyclohexyl)urea 510 (M + H) 1
2121 N-(cis-4-{[4-(dimethylamino)quinoiin-2-yl]amino}cyclohexyl)-
N'-(3-methyl-5-phenylisoxazol-4-yl)urea 485 (M + H) 2
2122 N-(cis-4-{[4-(dimethylamino)quinolin-2-yi]amino}cyclohexyi)-
N'-[5-methy]-2-(trifluoromethyI)-3-furyI]urea 476 (M + H) -i
2123 N-(2-bromophenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)urea 482 (M + H) -*>
2124 N-biphenyl-2-yl-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino]cyclohexYl)urea 480 (M + H) 3
2125 N-butyl-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
y!lamino}cyclohexyl)urea 384 (M + H) 3
2126 N-(cis-4-{[4-(dimethyiamino)quinoIin-2-yl]amino}cyclohexyl)-
N'-(2,3-dimethylphenyl)urea 432 (M + H) 3
2127 ethyl 3-({[(cis-4-{[4-(dimethylamino)quinolin-2-
y l]amino} cyclohexyl)aminolcarbonyl} amino)benzoate 476 (M + H) 3
2128 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
N'-fl-(3-isopropenylphenyl)-l-methyIethyllurea 486 (M + H) i
2129 methyl N-{[(cis-4-{[4-(dimethylamino)quinoIin-2-
yl]amino}cyclohexyl)aminolcarbonvl}methioninate 474 (M + H) ->
2130 N-(cis-4- {[4-(dimethyIamino)quinolin-2-yl]amino} cyclohexy 1)-
N'-l-naphthylurea 454 (M + H) 1
2131 N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyC1-5hexyl)-
N'-[(2S)-2-phenylcyclopropyl]urea 444 (M + H) 3
2132 N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexyl)-
N'-(4-phenoxyphenyI)urea 496 (M + H)
2133 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-
N'-pentylurea 398 (M + H) 3
2134 N-(cis-4-{[4-(dimethyIamino)quinoiin-2-yI]amino}cyclohexyl)-
N'-fl -(1 -naphthyl)ethy Hurea 482 (M + H) 1
2135 methyl N-{[(cis-4-{[4-(dimethyIamino)quinoIin-2-
yl]amino}cyclohexyl)amino]carbonyl}phenylalaninate 490 (M + H) 2
2136 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
N'-( I -phenylethyl)urea 432 (M + H) 3
2137 1 -[4-(4-Dimethy Iamino-quinolin-2-yIamino)-cyclohexyl]-3-( 1 -
phenyl-ethyl)-urea 432 (M + H) 3
2138 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-
Nf-(2,3,5,6-tetrachlorophenyl>urea 540 (M + H)
2139 N-(2,4-dibromophenyl)-Nt-(cis-4-{[4-(dimethyIamino)quinolin-2-
ynamino}cyclohexyl)urea 560 (M + H)
2140 N-(2,4-dichlorobenzyI)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)urea 486 (M + H) 3
2141 N-t2,4-dimethoxyphenyl)-Nh-(cis-4-{[4-(dimethylamino)quinolin-
2-yllamino}cyclohexyl)urea 464 (M + H) 3

468

Ex. No. compound name MS class
2142 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-
N'-( 2 -ethoxy pheny 1 )urea 448 (M + H) 3
2143 N-(cis-4-{[4-(dimethyIaminoJquinolin-2-yl]amino}cyclohexy])-
N'-(2-fluorobenzyl)urea 436 (M + H)
2144 N-(cis-4-{[4-(dimethyIamino)quinoIin-2-yl]amino}cyclohexyl)-
N'-(2-methyl-4-nitrophenyI)urea 463 (M + H)
2145 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-
N'-(2-methyl-5-nitrophenyI)urea 463 (M + H) ->
2146 N-(cis4-{[4-(dimethylamino)quinolin-2-yI]amino}cyC1-5hexyl)-
N'-(2-m ethy 1 ben zy 1 )urea 432 (M + H) ■>
2147 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yI]amino}cyclohexyl)-
N'-(2-nitrophenyl)urea 449 (M + H) 3
2148 N-l,3-benzodioxol-5-yl-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
y!lamino}cyclohexyl)urea 448 (M + H)
2149 N-(cis-4-{[4~(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
N'-(3,4,5-trimethoxypheny])urea 494 (M + H) 1
2150 N-(3,4-dimethoxyphenyl)-N'-(cis-4- {[4-(dimethyIamino)quinolin-
2-yl]amino}cyclohexyl)urea 464 (M + H)
2151 N-(3-chloro-4-methoxyphenyl)-N'-(cis-4-{[4-
(dimethylamino)quinolin-2-ynamino}cyclohexvl)urea 468 (M + H)
2152 N-[4-bromo-2-(trifluoromethyl)phenyl]-N'-tcis-4-{[4-
(dimethyIamino)quinolin-2-yllamino}cyclohexyl)urea 550 (M + H)
2153 N-(4-bromobenzyl)-N'-(cis-4- {[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)urea 496 (M + H) 3
2154 N-(4-chloro-2-methylphenyl)-N'-(cis-4- {[4-
(dimethylamino)quinoIin-2-yl]amino}cyclohexvl)iJrea 452 (M + H) 3
2155 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-
N'-(4-fluorobenzyl)urea 436 (M + H)
2156 N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexyl)-
N'-(4-methoxy-2-methylphenyi)urea 448 (M + H) 3
2157 N-(5-chIoro-2,4-dimethoxyphenyl)-N'-(cis-4-{[4-
(dimethylarnino)quinolin-2-yl]amino}cyclohexyl)urea 498 (M + H) 1
2158 N-[ 1 -(4-bromopheny I)ethy l]-N'-(c is-4- {[4-
(dimethyIamino)quinoIin-2-yllamino}cyclohexyl)urea 510 (M + H)
2159 N-(4-bromo-2-methyIphenyl)-N'-(cis-4- {[4-
(dimethylamino)quinoIin-2-yIlamino}cyC1-5hexyl)urea 496 (M + H) 2
2160 ethyl N-{[(cis-4-{[4-(dimethylaniino)quinolin-2-
yl]amino}cvclohexyl)amino]carbonyl}phenylalaninate 504 (M + H) 3
2161 N-(2,3-dihydro-1,4-benzodioxin-6-y l)-N'-(cis-4- {[4-
(dimethylamino)quinolin-2-vnamino}cyclohexyl)urea 462 (M + H) 3
2162 N-(2,6-dibromo-4-isopropylphenyl)-N'-(cis-4- {[4-
fdimethyIamino)quinoIin-2-yl]amino}cyclohexyl)urea 602 (M + H) J
2163 N-[3-(cyclopentyIoxy)-4-methoxyphenyl]-N'-(cis-4-{[4-
(dimethylamino)quinolin-2-yl]amino}cyclohexyl)urea 518 (M + H) 3
2164 N-(3,4-dihydro-2H-l,5-benzodioxepin-7-yl)-N'-(cis-4-{[4-
(dimethylamino)quinolin-2-yIlamino}cyclohexyI)urea 476 (M + H) i
2165 N-(4-buty!-2-methylpheny I)-N'-(cis-4- {[4-
(dimethylamino)quinolin-2-yI]amino}cyC1-5hexyi)urea 474 (M + H)

469

Ex. No. compound name MS class
2166 N-(cis-4-{[4-{dimethylamino)quinolin-2-yI]amino}cyclohexyI)-
N'-(5-methyl-3-phenylisoxazol-4-yl)urea 485 (M + H) 3
2167 N-(4-bromophenyI)-N'-(cis-4-{[4-tdimethylamino)quinolin-2-
ynamino}cyclohexyl)thiourea 498 (M + H) J
2168 N-(4-cyanophenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)thiourea 445 (M + H) J
2169 N-(2,4-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cydohexyl)thiourea 488 (M + H) ">
2170 N-(2,4-dimethoxyphenyI)-Nl-(cis-4-{E4-{dimethylamino)quinolin-
2-yl]amino}cyclohexyl)thiourea 480 (M + H) 2
2171 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
N'-(2,6-dimethyIphenyI)thiourea 448 (M + H)
2172 N-(cis-4- {[4-(dimethy lamino)quinolin-2-yl]amino} cyclohexy 1)-
N'-(2-ethyl-6-isopropylphenyl)thiourea 490 (M + H) ">
2173 N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyC1-5hexyl)-
N'-(2-methoxyphenyl)thiourea 450 (M + H) 3
2174 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-
N'-l-naphthylthiourea 470 (M + H) 3
2175 N-(cis-4- {[4-(dimethy lamino)quinolin-2-yl]amino} cyclohexyl)-
N'-(3,4,5 -trimeth oxyph eny 1 )th i ourea 510 (M + H) 1
2176 N-(3,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-
2-yllamino)cyclohexyl)thiourea 480 (M + H) 3
2177 N-[4-(dimethyiamino)-1 -naphthyl]-N'-(cis-4- {[4-
(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)thiourea 513 (M + H) 2
2178 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
N'-(2-ethyIpheayl)thiourea 448 (M + H)
2179 N-(2-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllaminolcyclohexyl)urea 389 (M + H) 3
2180 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl jamino} cyclohexy 1)-
N'-(2,6-dimethyIphenyl)urea 383 (M + H)
2181 N-(2,4-difluorophenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-
2-yl]amino}cyclohexyI)urea 391 (M + H)
2182 N-{cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2-ethyI-6-methytphenyi)urea 397 (M + H) 3
2183 ethyl N-{[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amtno}cyclohexyi)amino]carbonyl}leucinate 421 (M + H) -■>
2184 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
N'-(4-fluorophenyl)urea 373 (M + H) ->
2185 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-C4-(methylthio>phenynurea 401 (M + H) -i
2186 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-f2-(trifluoroniethyl)phenynurea 445 (M + Na)
2187 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-mesitv!urea 397 (M + H) 2
2188 N-{cis-4-{[4-{dimethylamino)pyriniidin-2-yl]amino}cyclohexyl)-
N'-(2 -methyl ph eny 1 )u rea 369 (M + H) 3
2189 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2,4,6-trichlorophenyl)urea 457 (M + H) 1

470

Ex. No. compound name MS class
2190 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
N'-(2,4,6-tribromopheny])urea 588 (M + H) 1
2191 N-(2,4-dibromo-6-fluoropheny l)-N'-(cis-4- {[4-
(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)urea 529 (M + H) 1
2192 N-(2,6-diethylphenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)urea 411 (M + H) 3
2193 N-[2-chloro-6-(trif!uoromethyl)phenyl]-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yl]arnino}cyclohexyl)urea 457 (M + H) ■■>
2194 N-(2-chloro-6-methylphenyl)-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yilamino}cyclohexyl)urea 403 (M + H) 3
2195 N-(2-chlorobenzyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl"|amino}cyclohexy])iirea 403 (M + H)
2196 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-
N'-(2-ethyl-6-isopropyIphenyI)urea 447 (M + Na) 3
2197 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2-ethylphenyl)urea 383 (M + H) -i
.}
2198 N-(cis-4- {[4-(dimethy lamino)pyrimidin-2-yl]araino} cyclohexy 1)-
N' -(2 -iodo pheny 1 )urea 481 (M + H) 3
2199 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2-isopropyl-6-methylphenyI)urea 411 (M + H) 3
2200 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2-isopropylphenyl)urea 397 (M + H) 3
2201 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2-methyl-3-nitrophenyI)urea 414 (M + H)
2202 N-(cis-4- {[4-(dimethy Iamino)pyrimidin-2-y l]amino} cyclohexyl)-
N'-(2-propy]phenyl)urea 397 (M + H) 3
2203 N-(2-tert-butyi-6-methylphenyl)-N'-(cis-4- {[4-
(dimethyIamino)pyrimidin-2-yl]amino)cyclohexyl)urea 425 (M + H)
2204 N-(2-tert-butylphenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino} cyclohexy!)urea 411 (M + H) 3
2205 N-(3-chloro-2-methylphenyI)-N'-(cis-4-{[4-
fdimethylamino)pyrimidin-2-y!]amino}cyclohexyl)urea 403 (M + H)
2206 N-(4-bromo-2,6-difiuorophenyI)-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-ynamino}cyclohexyl)urea 469 (M + H)
2207 N-[4-chloro-2-(trifluoromethyI)phenyl]-N'-(cis-4- {[4-
(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)urea 457 (M + H) ->
2208 N-(4-cyanophenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cvclohexyl)urea 380 (M + H) -i
2209 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(diphenylmethyl)urea 445 (M + H) 1
2210 N-(4-bromo-2,6-dimethylpheny I)-N'-(cis-4- {[4-
(dimethylamino)pyrimidin-2-yllamino}cyC1-5hexyl)urea 461 (M + H) 1
2211 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
N'-(3 -methyl -5 -pheny lisoxazoI-4-y I )urea 436 (M + H) 3
2212 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-y]]amino}cyclohexyl)-
N'-r5-methyI-2-(trifluoromethyI)-3-furyIlurea 427 (M + H) 3
2213 N-(2-bromophenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)urea 433 (M + H)

471

Ex. No. compound name MS class
2214 N-biphenyl-2-yl-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)urea 431 (M + H) 3
2215 N-buty!-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)urea 335 (M + H) -i
2216 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
N'-(2,3-dimethyIphenyl)urea 383 (M+H) 3
2217 ethyl 3-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)amino]carbonyl}amino)benzoate 427 (M + H)
2218 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
N'-f 1 -(3-isopropenylpheny 1V1 -methyl ethyl] urea 437 (M + H)
2219 methyl N- {[(cis-4- {[4-(dimethyIamino)pyrimidin-2-
vllamino)cyclohexyl)aminolcarbonyl)methioninate 425 (M + H)
2220 N-(cis-4-{[4-(dimethyiamino)pyrimidin-2-yl]amino}cyclohexyI)-
N'-l-naphthylurea 405 (M + H)
2221 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-[(2S)-2-phenyIcyclopropyl]urea 395 (M + H)
2222 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(4-phenoxyphenyl)urea 447 (M + H)
2223 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
N'-pentylurea 349 (M + H) 3
2224 N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexyl)-
NT-[" 1 -(1 -naphthyl)ethyllurea 433 (M + H) 1
2225 methyl N-{[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino)cyclohexyl)amino]carbonyl}phenylalaninate 441 (M + H) 3
2226 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
N'-( 1 -phenylethyl)urea 383 (M + H) -i
2227 l-[4-(4-Dimethylamino-pyrimidin-2-ylamino)-cyC1-5hexyl]-3-(l-
phenyl-ethyl)-urea 383 (M + H)
2228 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2,3,5,6-tetrachlorophenyl)urea 491 (M + H) ->
2229 N-(2,4-dibromophenyl)-N'-(cis-4-{[4-(dimethylamino)pyrirnidin-
2-yllamino}cyclohexyl)urea 511 (M + H) 3
2230 N-t2,4-dichlorobenzyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-
2-yllamino}cyclohexyI)urea 437 (M + H) 3
2231 N-(2,4-dimethoxyphenyl)-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yllamino}cvclohexyl)urea 415 (M + H) 3
2232 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2-ethoxyphenyl)urea 399 (M + H)
2233 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
N'-(2-fIuorobenzyl)urea 387 (M + H)
2234 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
Nr-(2-methyl-4-nitrophenyl)urea 414 (M + H) 3
2235 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
N'-(2-methyl-5-nitrophenyl)urea 414 (M + H) 3
2236 N-(cis4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2-methylbenzyl)urea 383 (M + H) j
2237 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2-nitrophenyl)urea 400 (M + H) ->

472

Ex. No. compound name MS class
2238 N-l,3-ben2odioxol-5-yl-N'-(cis-4-{[4-(dimethylamino)pyrimidin-
2-yI]amino}cyC1-5hexyl)urea 399 (M + H) ->
2239 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyclohexyl)-
N'-(3,4,5-trimethoxyphenyl)urea 445 (M + H) 1
2240 N-(3,4-dimethoxyphenyl)-N'-tcis-4-{[4-
(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)urea 415 (M + H)
2241 N-t3-chloro-4-methoxyphenyl)-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yIlamino}cyC1-5hexy])urea 419 (M + H) ■-j
2242 N-[4-bromo-2-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-
{dimethylamino)pyrimidin-2-yIlamino}cyclohexyl)urea 501 (M + H) j
2243 N-(4-bromobenzyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
ynamino}cyclohexyl)urea 447 (M+H) ■->
2244 N-(4-cbloro-2-methylphenyl)-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yllamino}cyclohexyl)urea 403 (M + H) 2
2245 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
N'-(4-fluorobenzy 1 )urea 387 (M + H)
2246 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(4-methoxy-2-methylphenvI)urea 399 (M + H)
2247 N-(5-chloro-2,4-dimethoxyphenyl)-N'-(cis-4-{[4-
(dimethyIamino)pyrimidin-2-yllamino}cyclohexyl)urea 449 (M + H) 1
2248 N-[l-(4-bromophenyl)ethyl]-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yllamino}cyclohexyl)urea 461 (M + H) 3
2249 N-(4-bromo-2-methylphenyl)-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)urea 447 (M + H) 2
2250 ethyl N-{[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexy])aminolcarbonyl}phenylalaninate 455 (M + H) *">
2251 N-(2,3-dihydro-l,4-benzodioxin-6-yl)-N'-(cis-4-{[4-
(dimethylamino)pyrimidm-2-yl]amino}cyclohexyI)urea 413 (M + H)
2252 N-(2,6-dibromo-4-isopropylphenyl)-N'-(cis-4-{[4-
(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyl)urea 553 (M + H) 2
2253 N-[3-(cyclopentyloxy)-4-methoxyphenyI]-N'-(cis-4-{[4-
(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyI)urea 469 (M + H) 2
2254 N-(3,4-dihydro-2H-l,5-benzodioxepin-7-yI)-NT-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yI]amino}cycfohexyl)urea 427 (M + H)
2255 N-(4-butyl-2-methylphenyl)-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-vllamino}cyclohexyl)urea 425 (M + H) 3
2256 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(5-methyl-3-phenylisoxa2ol-4-yl)urea 436 (M + H) i
2257 N-(4-bromophenyl)-N'-(cis-4- {[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)thiourea 449 (M + H) 3
2258 N-(4-cyanophenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino) cyclohexyl)thiourea 396 (M + H) 2
2259 N-(2,4-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-
2-yllamino}cyC1-5hexy!)thiourea 439 (M + H) i
J
2260 N-(2,4-dimethoxyphenyl)-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)thiourea 431 (M + H) 2
2261 N-(cis-4-{[4-(dimethy!amino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2,6-dimethyIphenyI)thiourea 399 (M + H) 3

473

Ex. No. compound name MS class
2262 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyI)-
N'-(2-ethyl-6-isopropyIphenyI)thiourea 441 (M + H)
2263 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2-methoxyphenyI)thiourea 401 (M + H) -i
2264 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yi]amino}cyclohexyl)-
N'-l-naphthylthiourea 421 (M + H)
2265 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(3,4,5-trimethoxyphenyI)thiourea 461 (M + H) 1
2266 N-(3,4-dimethoxyphenyl)-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yI]amino}cyclohexyI)thiourea 431 (M + H) 2
2267 N-[4-(dimethylamino)-I-naphthyl]-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yl]amino)cyclohexyl)thiourea 464 (M + H) 2
2268 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
N'-(2-ethylphenyl)thiourea 399 (M + H)
2269 N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-
N'-(2-methoxy-4-nitrophenyl)thiourea 495 (M + H)
2270 N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyi)-
N'-(2-methoxy-5-methy]phenyl)thiourea 464 (M + H)
2271 N-(4-bromo-2-chIorophenyI)-N'-tcis-4- {[4-
(dimethylamino)quinolin-2-yl]amino)cyclohexyl)thiourea 532 (M + H)
2272 N-(cis-4-{[4-(dimethyIamino)quinoIin-2-yl]amino}cyclohexyl)-
N'-(4-iodophenyl)thiourea 546 (M + H) 3
2273 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-
N'-(2,4,6-tribromophenyI)thiourea 653 (M + H) 1
2274 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
N'-(2,4,6-trichIorophenyl)thiourea 522 (M + H) 2
2275 N-(cis-4-{[4-(dimethy!amino)quinoIin-2-yl]amino}cyclohexyl)-
N'-mesitylthiourea 462 (M + H) 1
2276 N-(cis-4-{[4-(dimethyIamino)quinoIin-2-yl]amino}cyclohexyl)-
N'-(2,4-dimethylphenyl)thiourea 448 (M + H)
2277 N-(2,6-diethylphenyI)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yllamtno}cvclohexyl)thiourea 476 (M + H) 1
2278 N-(2-bromo-4-methylphenyI)-N'-(cis-4- {[4-
(dimetbytamino)quinolin-2-yI]aniino}cyclohexyI)thiourea 512 (M + H) 3
2279 N-(2-ch!orobenzyI)-N'-(cis-4-{[4-(dimethyIamino)quinolin-2-
Yllaminolcyclohexy])thiourea 468 (M + H)
2280 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
N'-(2-ethy 1-6-methy Iph eny 1 )th i ourea 462 (M + H)
2281 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyC1-5hexyl)-
Nt-(2-isopropylphenyl)thiourea 462 (M + H) J
2282 methyl 3-({[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)aminolcarbonothioyl}amtno)benzoate 478 (M + H) *>
2283 N-(4-bromo-2,6-dimethylphenyI)-N'-(cis-4-{[4-
(dimethyIamino)quinolin-2-yIlamino)cyclohexyl)thiourea 526 (M + H) 1
2284 N-(4-bromo-2-methyIphenyI)-N'-(cis-4-{[4-
(dimethylamino)quinoIin-2-vIlamino}cyclohexyl)thiourea 512 (M + H) 2
2285 N-[4-bromo-2-(trifluoromethyI)pheny!]-Nl-(cis-4- {[4-
(dimethy]amino)quinolin-2-yilamino}cyclohexyl)thiourea 566 (M + H) 2

474

Ex. No. compound name MS class
2286 N-(4-chloro-2-methyIphenyl)-N'-(cis-4-{[4-
(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)thiourea 468 (M + H) ->
2287 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-
N'-(l-naphthyImethyl)thiourea 484 (M + H)
2288 N-t2,3-dimethoxyben2yl)-N'-(cis-4-{[4-(dimethyIamino)quinolin-
2-yl]amino}cyclohexyl)thiourea 494 (M + H)
2289 N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-
N'-(2,4,5-trimethyIphenyl)thiourea 462 (M + H) 3
2290 N-biphenyI-2-yl-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyi)thiourea 496 (M + H)
2291 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yI]amino}cyclohexyI)-
N'-(2-methyI-4-nitrophenyI)thiourea 479 (M + H)
2292 N-(3-chIorobenzyI)-N'-(cis-4-{[4-(dimethylamino)quinoiin-2-
yllamino}cyclohexyl)thiourea 468 (M + H) ->
J
2293 ethyl 3-({[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)amino]carbonothioy!}amino)benzoate 492 (M + H) 3
2294 N-[4-chIoro-2-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-
(dimethylamino)quinolin-2-ynamino}cyclohexyl)thiourea 522 (M + H)
2295 N-(cis-4-{[4-(dimethy]amino)quinoIin-2-yl]amino}cyclohexyl)-
N'-(4-fluoro-2-methylphenyl)thiourea 452 (M + H) J
2296 N-(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}cyclohexyl)-
N'-(4-methoxy-2-methyIphenyl)thiourea 464 (M + H) -i
2297 N-(5-chloro-2T4-dimethoxyphenyl)-N'-(cis-4-{[4-
(dimethylamino)quinolin-2-yllamino}cyclohexyl)thiourea 514 (M + H) 1
2298 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyC1-5hexyl)-
N'-[( 1 R)-I -phenylethyl]th iourea 448 (M + H) 3
2299 N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-
N'-(2,3-dimethylphenyI)thiourea 448 (M + H) 3
2300 N-(2,4-dibromo-6-fluorophenyl)-N'-tcis-4-{[4-
(dimethy]amino)quinoIin-2-yl]amino}cyclohexyl)thiourea 594 (M + H) 2
2301 N-(2,4-dichIoro-6-methylphenyi)-N'-(cis-4- {[4-
(dimethylamino)quinolin-2-yI]amino}cyclohexyl)thiourea 502 (M + H) 1
2302 N-(cis-4- {[4-(dimethylamino)quinoIin-2-yl]amino} cyclohexyi)-
N'-(2-ethoxyphenyI)th iourea 464 (M + H)
2303 N-(cis-4-{[4-(dimethy[amino)quinolin-2-yI]amino}cyclohexyl)-
N'-(2-isopropyI-6-methyIphenyl)th iourea 476 (M + H)
2304 N-(2,3-dihydro-l,4-benzodioxin-6-yl)-N'-(cis-4-{[4-
(dimethylamino)quino}in-2-yIlamino}cyclohexyJ)thiourea 478 (M + H)
2305 N-1,3-benzodioxol-5-y!-N'-(cis-4- {[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)thiourea 464 (M + H)
2306 N-(3-chIoro-2-methylphenyI)-N'-(cis-4- {[4-
(ditnethyIamino)quinoIin-2-yllamino}cyC1-5hexyl)thiourea 468 (M + H)
2307 N-[4-bromo-2-(trifluoromethoxy)pheny]]-N'-(cis-4-{[4-
(dimethylammo)quinoIin-2-yIlamino}cyclohexyl)thiourea 582 (M + H) 3
2308 N-(4-chloro-255-dimethoxypheny])-N'-(cis-4-{[4-
{dimethy]amino)quinolin-2-yI]amino}cyclohexyI)thiourea 514 (M + H) -i
2309 N-(cis-4-{[4-(dimethyIamino)quinolin-2-y]]amino}cyclohexyl)-
N'-(5-methyI-3-phenyIisoxazoI-4-yl)thiourea 501 (M + H)

475

Ex. No. compound name MS class
2310 N-bicyclo[2.2.I]hept-2-yI-N'-(cis-4-{[4-(diraethylamino)quinolin-
2-yllamino}cyclohexyl)thiourea 438 (M + H) ->
2311 methyl 3-({[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)amino]carbonothioyl}amino)-4-
methyIthiophene-2-carboxylate 498 (M + H) 2
2312 methyl 3-({[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)amino]carbonothioyl}amino)thiophene-2-
carboxylate 484 (M + H)
2313 N-(4-butyl-2-methy lphenyI)-N'-(cis-4- {[4-
(dimethyIamino)quinolin-2-yI]amino}cyclohexyl)thiourea 490 (M + H)
2314 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
Nt-f2-methoxy-4-nitrophenyl)thiourea 446 (M + H) -*>
J
2315 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2-methoxy-5-methy]phenyl)thiourea 413 (M-H) 3
2316 N-(4-bromo-2-chlorophenyl)-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2'yllamino}cyclohexyl)thiourea 483 (M + H) 3
2317 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(4-iodophenvl)thiourea 497 (M + H)
2318 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2,4,6-tribromophenyl)thiourea 604 (M + H) 1
2319 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2,4,6-trichlorophenyl)thiourea 473 (M + H) ->
2320 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-mesitylthiourea 413 (M + H) 1
2321 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2,4-dimethylphenyl)thiourea 399 (M + H) ->
2322 N-(2!6-diethylphenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)thiourea 427 (M + H) 3
2323 N-(2-bromo-4-methylphenyl)-N'-(cis-4- {[4-
(dimethylamino)pyrimidin-2-yllamino}cyclohexyl)thiourea 463 (M + H)
2324 N-(2-chlorobenzyI)-N'-(cis-4- {[4-(dimethy lamino)pyrimidin-2-
yilamino}cyclohexyl)thiourea 419 (M + H) ~i
2325 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2-ethyl-6-methylphenyl)thiourea 413 (M + H) 3
2326 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2-isopropylphenyl)thiourea 413 (M + H) 3
2327 methyl 3-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)aininolcarbonothioy]}amino)benzoate 429 (M + H) 3
2328 N-(4-bromo-2,6-dimethylphenyl)-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)thiourea 477 (M + H) 1
2329 N-(4-bromo-2-methylphenyl)-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)thiourea 463 (M + H) ->
2330 N-[4-bromo-2-(trifluoromethyt)phenyl]'Nt-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)thiourea 517 (M + H)
2331 N-(4-chloro-2-methylphenyl)-N'-(cis-4- {[4-
(dimethylamino)pyrimidin-2-yl"[amino}cyclohexyl)thiourea 419 (M + H) -i
2332 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(l-naphthylmethyl)thiourea 435 (M + H)

476

Ex. No. compound name MS class
2333 N-(2,3-dimethoxybenzyl)-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yI|amino)cvclohexYl)thiourea 443 (M - H)
2334 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
N'-(2,4,5-trimethylphenyI)thiourea 413 (M + H) ■->
2335 N-bipheny l-2-yl-N'-(cis-4- {[4-(dimethyIamino)pyrimidin-2-
yllamino}cyc]ohexyl)thiourea 447 (M + H) 3
2336 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2-methyl-4-nitrophenyl)thiourea 428 (M - H) 3
2337 N-(3-chlorobenzyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyC1-5hexyl)thiourea 419 (M + H) ->
2338 ethyl 3-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino)cyclohexYl)arainolcarbonothioyl}amino)benzoate 441 (M-H) 3
2339 N-[4-chloro-2-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-ynamino)cyclohexyl)thiourea 473 (M + H) 3
2340 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
N'-(4-fluoro-2-methy]phenyI)thiourea 403 (M + H)
2341 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(4-methoxy-2-methylphenyl)thiourea 415 (M + H)
2342 N-(5-chloro-2,4-dimethoxyphenyI)-N'-(cis-4-{[4-
(dimethyIamino)pyrimidin-2-ynamino}cyclohexvl)thiourea 465 (M + H) 1
2343 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-f(lRVl-phenyIethyllthtourea 397 (M-H) 3
2344 N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2,3-dimethylphenyI)thiourea 399 (M + H) 3
2345 N-(2,4-dibromo-6-fluorophenyl)-N'-(cis-4- {[4-
(dimethylamino)pyrimidin-2-yllamino}cyC1-5hexyl)thiourea 545 (M + H) 2
2346 N-(2,4-dichIoro-6-methylphenyI)-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yllamino}cyclohexyl)thiourea 453 (M + H) 2
2347 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
N'-(2-ethoxyphenyI)thiourea 415 (M + H) i
2348 N-(cis-4- {[4-(dimethy lamino)pyrimidin-2-yl]amino} cyclohexy 1)-
N'-(2-isopropyl-6-methylphenyl)thiourea 427 (M + H) ■-*
2349 N-(2,3-dihydro-1,4-benzodioxin-6-yl)-N'-(cis-4- {[4-
(dimethylamino)pyrimidin-2-yI]amino}cyC1-5hexyl)thiourea 429 (M + H)
2350 N-l,3-benzodioxol-5-yl-Nr-(cis-4-{[4-(dimethy!amino)pyrimidin-
2-yl]amino}cyclohexyl)thiourea 415 (M + H) 3
2351 N-(3-chIoro-2-methylpheny])-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)thiourea 419 (M + H)
2352 N-[4-bromo-2-(trifluoromethoxy)phenyI]-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yllamino}cyclohexyl)thiourea 533 (M + H)
2353 N-(4-chIoro-2,5-dimethoxypheny l)-N'-(cis-4- {[4-
(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)thiourea 465 (M + H) 3
2354 N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyclohexyl)-
N'-(5-methyl-3-phenylisoxazoI-4-yl)thiourea 452 (M + H) 3
2355 N-bicyclo[2.2.I]hept-2-yl-N'-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yllamino}cyclobexyl)thiourea 387 (M-H)

477

Ex. No. compound name MS class
2356 methyl 3-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)amino]carbonothioyl}amino)-4-
methyIthiophene-2-carboxylate 449 (M + H) •■>
2357 methyl 3-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)amino]carbonothioyI}amino)thiophene-2-
carboxylate 435 (M + H) ->
2358 N-(4-buty l-2-methy Iphenyl)-N'-(cis-4- {[4-
(dimethylamino)pyrimidin-2-yllamino}cyC1-5hexyl)thiourea 441 (M + H)
2359 N-(2-chIorophenyl)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyllurea 452 (M + H)
2360 N-[(cis-4'{[4-(dimethylamino)quinoIin-2-
yllamino}cyC1-5hexyl)methyll-N'-(2,6-dimethylphenyl)urea 446 (M + H) 3
2361 N-(2,4-difluorophenyI)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]aminolcyclohexyl)methyl]urea 454 (M + H) ~i
2362 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino)cyclohexyl)methyll'N'-(2-ethyl-6-methylphenyl)urea 460 (M + H) 2
2363 ethyl N-( {[(cis-4- {[4-(dimethylamino)quinolin-2-
ynamino}cyclohexyl)methyl]amino}carbonyl)leucinate 484 (M + H) ->
2364 N-[(cis-4- {[4-(dimethylamino)quinolin-2-
yI]amino}cyclohexyl)methyll-N'-(4-fluorophenyI)urea 436 (M + H) 3
2365 N-[(cis-4-{[4-(dimethylamino)quinolm-2-
yllamino)cyclohexvl)methyll-N'-[4-(methylthio)phenyl]urea 464 (M + H) ■i
2366 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
ynamino}cyC1-5hexyl)methyl]-NI-f2-(trifluoromethyI)phenyl]urea 486 (M + H)
2367 N-[(cis-4-{[4-(dimethylamino)quinoIin-2-
yllamino}cyclohexyl)methvl]-N'-mesitylurea 460 (M + H) 2
2368 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyll-N'-(2-methylphenyl)urea 432 (M + H) -i
2369 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yI]amino)cyclohexyl)methyl]-N'-(2,4,6-trichlorophenyl)urea 520 (M + H) 1
2370 N-[(cis-4- {[4-(dimethylamino)quinolin-2-
yllaminoicyC1-5hexyl)methyll-N'-(2,4,6-tribromophenyl)urea 651 (M + H) 1
2371 N- (dtmethyIamino)quinolin-2-yl]amino}cyctohexyl)methyl]urea 592 (M + H) 1
2372 N-(2,6-diethylphenyl)-N'-[(ciS'4-{[4-(dimethyIamino)quinolin-2-
yllamino} cyclohexyl)methyl]urea 474 (M + H) 2
2373 N-[2-chloro-6-(trifluoromethyl)phenyl]-N'-[(cis-4~ {[4-
(dimethyIamino)quinolin-2-yllamino}cyC1-5hexyl)methyl]urea 520 (M + H) 2
2374 N-(2-chloro-6-methy!phenyl)-N'-[(cis-4-{[4-
(dimethylamino)quinolin-2-yllatnino}cyclohexyl)methyllurea 466 (M + H) *>
2375 N-(2-chIorobenzyl)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-
yilamino}cyclohexyl)methyllurea 466 (M + H) ->
2376 N-[(cis-4- {[4-(dimethy lamino)quino!in-2-
ynamino}cyclohexyI)methyl]-N'-(2-ethyl-6-isopropylphenyl)urea 488 2377 N-[(cis-4- {[4-(dimethylamino)quinolm-2-
yl]amino)cyclohexyl)methyll-N'-(2-ethyIphenvl)urea 446 (M + H) ->
2378 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyll-N'-(2-iodophenyl)urea 544 (M + H) 3

478

Ex. No. compound name MS class
2379 N-[(cis-4-{[4-(diinethylamino)quinolin-2-yl]amino}cyclohexyi)-
methYlVN'-(2-isopropyl-6-methylphenvl)urea 474 (M + H) 2
2380 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyI)methyI]-N'-(2-isopropylphenyl)urea 460 (M + H) t
2381 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyC1-5hexyI)methyIl-N'-(2-methyl-3-nitropheny])urea 477 (M + H) 2
2382 N-[(cis-4-{[4-(dimethylamino)quino]in-2-
yllamino}cyclohexyI)methyIl-N'-(2-propylphenyl)urea 460 (M + H) j
2383 N-(2-tert-butyl-6-methy]phenyl>N'-[(cis-4- {[4-
(dimethylamino)quinoIin-2-yl]amino}cyC1-5hexyi)methynurea 488 (M + H) 1
2384 N-(2-tert-butylphenyi)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexy])methvl]urea 474 (M + H) 1
2385 N-(3-chloro-2-methylphenyl)-N'-[(cis-4-{[4-
(dimethylamino)quino]in-2-yl]amino}cvclohexyl)methyllurea 466 (M + H) *>
2386 N-(4-bromo-2,6-difluorophenyl)-N'-[(cis-4-{[4-
(dimethylamino)quinolin-2-yl]amino}cvclohexyl)methyllurea 532 (M + H) 3
2387 N-[4-chloro-2-(trifluoromethyl)phenyl]-N'-[(cis-4- {[4-
(dimethylamino)quinolin-2-ynamino}cyclohexyI}methyl]urea 520 (M + H)
2388 N-(4-cyanophenyl)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-
y!lamino}cyclohexyl)methyllurea 443 (M + H) 3
2389 N-[(cis-4- {[4-(dimethy lamino)quinolin-2-
yl]amino}cyclohexyl)methyll-N'-(diphenylmethyl)urea 508 (M + H) 2
2390 N-(4-bromo-2,6-dimethy lphenyI)-N'-[(cis-4- {[4-
(dimethylamino)quino]in-2-yllamino}cyclohexyl)methyllurea 524 (M + H) 1
2391 N-[(cis-4-{[4-(diniethylamino)quinolin-2-yljamino}cyclohexyl)-
methyl"|-N'-(3-methyl-5-phenyIisoxazoI-4-yl)urea 499 (M + H) -i
2392 N-[(cis-4- {[4-(dimethy lamino)quinolin-2-y IJamino} cyclohexyl)-
methyil-Nr-f5-methyl-2-(trifluoromethyl)-3-furyllurea 490 (M + H) 3
2393 N-(3,5-dichlorophenyl)-N'-[(cis-4-{[4-(dimethylamino)quinolin-
2-yl]amino}cyclohexyl)methyI]urea 486 (M + H)
2394 N-(2,3-dichIorophenyl)-N'-[(cis-4-{[4-(dimethylamino)quinolin-
2-yllamino}cyclohexyl)methynurea 486 (M + H) 2
2395 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
ynamino}cyclohexyI)methyll-N'-(4-methylphenyl)urea 432 (M + H) 3
2396 N-(2,6-diisopropyIpheny!)-N'-[(cis^-{[4-
(dimethylamino)quinoIin-2-y!lamino}cyC1-5hexyl)methyl]urea 502 (M + H) 1
2397 N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
methyll-N'-(2,3-dimethyl-6-nitrophenyl)urea 491 (M + H) 3
2398 N-(2,6-dibromo-4-fluorophenyl)-N'-[(cis-4-{[4-
(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)methyIlurea 592 (M + H) 3
2399 N-(2,6-dichlorophenyI)-N'-[(cis-4-{[4-(dimethylamino)quinoIin-
2-yllamino}cyclohexyl)methy!lurea 486 (M + H)
2400 N-[(cis-4-{[4-(dimethyIamino)quinoIin-2-yl]amino}cyclohexyl)-
methyll-N'-(2-methoxy-5-methyIpheny])urea 462 (M + H)
2401 N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyC1-5hexy!)methyn-N'-(2-methyl-6-nitrophenyI)urea 477 (M + H) 3
2402 N-(3,4-difluorophenyl)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-
yllamino}cyclohexyl)methyllurea 454 (M + H) 3

479

Ex. No. compound name MS class
2403 N-(3,5-difluorophenyl)-N'-[(cis-4-{[4-(dimethylamino)quinoIin-2-
yllamino}cyclohexyl)methyl]urea 454 (M + H) 3
2404 N-(3-chloro-4-fluorophenyl)-N'-[(cis-4- {[4-
fdimethylamino)quinolin-2-yI]amino}cyclohexyl)methynurea 470 (M + H)
2405 N-(2-chIorophenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyllurea 403 (M + H)
2406 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyn-N'-(2,6-dimethylphenvl)urea 397 (M + H) 1
2407 N-(2,4-difIuorophenyI)-NI-[(cis-4-{[4-(dimethylamino)pyrimidin-
2-yI]amino}cyclohexyI)methyllurea 405 (M + H) 2
2408 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyll-N'-(2-ethyl-6-methylphenyl)urea 411 (M + H) 1
2409 ethyl N-( {[(cis-4- {[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyl)methyl]amino}carbonyl)leucinate 435 (M + H) 3
2410 N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yIlamino}cyclohexyI)methy]]-N'-(4-fluorophenyl)urea 387 (M + H) 2
2411 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino)cyclohexyl)methyll-N'-[4-(methylthio)phenyl]urea 415 (M + H) 3
2412 N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-
yilamino}cyclohexyl)methyl]-N'-[2-(trifluoromethyl)phenyllurea 435 (M-H)
2413 N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-
yllamino}cyclohexyI)methvl]-N'-mesitylurea 411 (M + H) 1
2414 N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-
yIlamino}cyc1ohexyl)methyIl-N'-(2-methylphenyl)urea 383 (M + H) 3
2415 N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]-N'-(2,4,6-trichIorophenyl)urea 471 (M + H) 1
2416 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
vI]amino)cyclohexyl)methyll-N'-(2,4,6-tribromophenvl)urea 602 (M + H) 1
2417 N-(2;4-dibromo-6-fluorophenyl)-N'-[(cis-4- {[4-
(dimethylamino)pyrimidin-2-yI]amino}cyC1-5hexyl)methyllurea 543 (M + H) 1
2418 N-(2,6-diethylphenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-
2-yl]amino}cyclohexyl)methyl]urea 425 (M + H) 1
2419 N-[2-chloro-6-(trifluoromethyl)phenyl]-N'-[(cis-4-{[4-
(dimethylamino)pyrimtdin-2-yI]amino}cYclohexyl)methyllurea 471 (M + H) 1
2420 N-(2-chIoro-6-methyIphenyI)-N'-[(cis-4-{[4-
(dimethylamino)pyrimidin-2-yI]amino}cyclohexvl)methyllurea 417 (M + H) 1
2421 N-(2-chIorobenzyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
ynamino} cyclohexy l)methy l]urea 417 (M + H) 3
2422 N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-
yI]amino}cyclohexyl)methyl]-N'-(2-ethy]-6-isopropylphenyl)urea 437 (M-H) 1
2423 N-[(cis-4-{[4-(dimethylamtno)pyrirnidin-2-
yIlamino}cyclohexyl)methyll-Nh-(2-ethyIphenyl)urea 397 (M + H) 3
2424 N-[(cis-4-{[4-(dimethyIamtno)pyrimidin-2-
yilamino}cyC1-5hexyl)methyl]-N'-(2-iodophenyl)urea 495 (M + H)
2425 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
methyl]-N'-(2-isopropyl-6-methylphenyl)urea 425 (M + H) 1
2426 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]-N'-(2-isopropylphenyl)urea 411 (M + H) 3

480

Ex. No. compound name MS class
2427 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
y]lamino}cyclohexy!)methyl]-N'-(2-methyl-3-nitrophenyI)urea 428 (M + H) 1
2428 N-[tcis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino)cyclohexyl)methyl"|-N'-(2-propylphenyl)urea 411 (M + H) 2
2429 N-(2-tert-butyl-6-methyIphenyl)-N'-[(cis-4-{[4-
(dimethylamino)pyrimidin-2-ynamino}cyclohexyl)methyllurea 439 (M + H) 1
2430 N-(2-tert-butylphenyi)-N'-[(cis-4-{[4-(dimethyIamino)pyrimidin-
2-yl]amino}cyclohexyl)methyl]urea 425 (M + H) 1
2431 N-(3-chloro-2-methylphenyl)-N'-[(cis-4-{[4-
(dimethylamino)pyrimidin-2-yllamino}cyclohexyI)methynurea 417 (M + H) 1
2432 N-(4-bromo-2,6-difluorophenyl)-N'-[(cis-4-{[4-
(dimethylamino)pyrimidin-2-yIlamino}cyclohexyl)methyllurea 483 (M + H) 1
2433 N-[4-chIoro-2-(trifluoromethyl)phenyI]-N'-[(cis-4- {[4-
(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)methyllurea 471 (M + H) 2
2434 N-(4-cyanophenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyllurea 394 (M + H) 3
2435 N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yllamino}cyclohexyl)methyll-N'-(diphenylmethyl)urea 459 (M + H) 1
2436 N-(4-bromo-2,6-dimethylphenyl)-N'-[(cis-4-{[4-
(dimethy]amino)pyrimidin-2-yllamino}cyc]ohexyl)methvllurea 475 (M + H) 1
2437 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
methyl]-N'-f3-methyl-5-phenylisoxazol-4-yl)urea 450 (M + H) 1
2438 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
methyl]-N'-f5-methyI-2-(trifluoromethyl)-3-furyllurea 441 (M + H) 3
2439 N-(3,5-dichlorophenyI)-Nt-[(cis-4-{[4-(dimethylamino)pyrimidin-
2-yl]amino}cyc]ohexv])methyIlurea 437 (M + H) 2
2440 N-(2,3-dichlorophenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-
2-yI]amino}cyclohexyl)methyl]urea 437 (M + H) 1
2441 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
y]lamino}cyclohexyl)methyll-N'-(4-methylphenyl)urea 383 (M + H)
2442 N-(2,6-diisopropylphenyI)-N'-[(cis-4-{[4-
(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]urea 453 (M + H) 1
2443 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-y]]amino}cyclohexyl)-
methyl]-N'-(2,3-dimethyI-6-nitrophenyI)urea 442 (M + H) 1
2444 N-(2,6-dibromo-4-fluorophenyl)-N'-[(cis-4-{[4-
(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)methyl]urea 543 (M + H) 1
2445 N-(2,6-dichiorophenyI)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-
2-yllamino}cyclohexyl)methyilurea 437 (M + H) 1
2446 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
methyn-N'-(2-methoxy-5-methylphenyl)urea 413 (M + H) 2
2447 N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yIlamino}cyC1-5hexyI)methyI]-N'-(2-methyl-6-nitrophenyl)urea 428 (M + H) 2
2448 N-(3,4-difluorophenyI)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-
2-yl]amino}cyclohexyl)methyIlurea 405 (M + H) 1
2449 N-(3,5-difIuorophenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-
2-yl]amino}cyclohexyl)methyl]urea 405 (M + H) 1
2450 N-(3-chloro-4-fluorophenyl)-N'-[(cis-4-{[4-
(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyllurea 421 (M + H) 1

481

Ex. No. compound name MS class
2451 N-(2-chIorophenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino)cyC1-5hexyl)methyl]urea 457 (M + H) ->
2452 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
ynamino)cyclohexyl)methyll-N'-(2,6-dimethylphenyl)urea 451 (M + H) 1
2453 N-(2,4-difluorophenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yIlamino}cyclohexyI)methyllurea 459 (M + H) 2
2454 N-[fcis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyclohexyl)methyIl-N'-(2-ethvI-6-methyIpheny!)urea 465 (M + H) 1
2455 ethyl N-({[(cis-4-{[4-tdimethyIamino)-5>6,7,8-tetrahydro
quinazolin-2-yl]amino}cyclohexyl)methyl]amino}carbonyl)-
leucinate 489 (M + H) 2
2456 N-[(cis-4-{[4-(dimethylamino)-5?6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methYll-N'-(4-fluorophenyl)urea 441 (M + H) 2
2457 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y!]amitio}cyclohexyl)methyl]-Nl-[4-(methylthio)phenvllurea 469 (M + H) 3
2458 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyl)methyll-N'-f2-(trifluoromethyl)phenyIlurea 491 (M + H) 3
2459 N-[(cis~4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyI)methyn-N'-mesitylurea 465 (M + H) 1
2460 N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexvl)methyl]-N'-(2-methvlphenyl)urea 437 (M + H) 3
2461 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y!lamino}cyclohexyI)methyl]-NI-(2,4,6-trichlorophenyl)urea 525 (M + H) 1
2462 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y!lamino}cyclohexyl)methyll-N'-(2,4,6-tribromophenyl)urea 657 (M + H) 1
2463 N-(2,4-dibromo-6-fluorophenyl)-N'-[(cis-4- {[4-(dimethy lamino)-
5,6,7,8-tetrahydroquinazolin-2-yllamino}cyclohexyl)methyl]urea 597 (M + H) -i
2464 N-(2,6-diethyIphenyl)-N'-[(cis-4-{[4-(dimethylamino>5,6,7,8-
tetrahydroquinazolin-2-yI]aminoicyclohexyI)methvllurea 479 (M + H) 1
2465 N-[2-chloro-6-(trifluoromethyl)phenyl]-N'-[(cis-4-{[4-(dimethyl-
amino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}cyclohexyl)-
methyl] urea 525 (M + H) 1
2466 N-(2-chloro-6-methylphenyI)-N'-[(cis-4-{[4-(diraethylamino)-
5,6,7,8-tetrahydroquinazolin-2-yllaminoicyc!ohexyl)methvllurea 471 (M + H) 1
2467 N-(2-chIorobenzyl)-N'[(cis-4-{t4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyi)methyllurea 471 (M + H) ■>
2468 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yllamino}cyclohexyl)methvl]-Nt-(2-ethyl-6-isopropylphenyl)urea 493 (M + H) 1
2469 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cyclohexyI)methyll-N'-(2-ethylphenyl)urea 451 (M + H) 3
2470 N-[(cis-4- {[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]-N'-(2-iodophenyl)urea 549 (M + H) -i
2471 N-[(cis-4- {[4-(dimethy Iamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]-Nf-(2-isopropyl-6-methylphenyI)-
urea 479 (M + H) 2
2472 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino)cyclohexyl)methyl]-N'-(2-isopropylphenyl)urea 465 (M + H) 3

482

Ex. No. compound name MS class
2473 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yI]amino}cyclohexyI)methy]]-N'-(2-methyl-3-nitrophenvl)urea 482 (M + H) 3
2474 N-[tcis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)methylVNT-(2-propylphenyl)urea 465 (M + H) 3
2475 N-(2-tert-butyI-6-methylphenyl)-N'-[(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahvdroquinazoIin-2-yllamino}cyclohexyl)methyllurea 493 (M + H) 1
2476 N-(2-tert-butylphenyl)-Nt-[tcis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)methyl]urea 479 (M + H) 2
2477 N-(3-chloro-2-methyIphenyl)-N'-[(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazolin-2-ynamino}cyclohexyl)methyllurea 471 (M + H) 2
2478 N-(4-bromo-2,6-difluorophenyl)-N'-[(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazoIin-2-y]lamino}cyc]ohexyl)methynurea 537 (M + H) ■^
2479 N-[4-chloro-2-(trifIuoromethyI)phenyl]-N'-[{cis-4-{[4-(dimethyI-
amino)-5,6,7,8-tetrahydroquinazolin-2-y]]amino}cyclohexyI)-
methyl]urea 525 (M + H) 3
2480 N-(4-cyanophenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydrqguinazol tn-2-y l]amino} cyclohexyl)methyl]urea 448 (M + H)
2481 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yllamino}cvC1-5hexvl)methyll-N'-fdiphenylmethvl)urea 513 (M + H) 3
2482 N-(4-bromo-2,6-dimethylphenyI)-N'-[(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahvdroquinazolin-2-yllamino}cyclohexvl)methyl]urea 529 (M + H) 1
2483 N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyI)methyI]-N'-(3-methyl-5-phenylisoxazol-
4-yl)urea 504 (M + H) -*>
2484 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl3-N'-[5-methyl-2-(trifluoromethyl)-3-
furyl]urea 495 (M + H)
2485 N-(3,5-dich)orophenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-y!]amino}cyclohexyl)methyl]urea 491 (M + H) -i
2486 N-(2,3-dich]orophenyI)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yllamino}cyclohexyl)methvl]urea 491 (M + H) -i
2487 N-[(cis-4-{[4-(dimethylamtno)-5,6,7,8-tetrahydroquinazolin-2-
yIlamino}cyC1-5hexyl)methyl]-N'-(4-methy!phenyI)urea 437 (M + H) 3
2488 N-(2J6-diisopropylphenyl)-N'-[(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazoIin-2-vIlamino}cyclohexy!)methyl]urea 507 (M + H) 2
2489 N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]-N'-(2,3-dimethyl-6-nitrophenyl)-
urea 496 (M + H) 2
2490 N-(2,6-dibromo-4-fluorophenyl)-N'-[(cis-4-{[4-(dimethylamino)-
5,6,7,8-tetrahydroquinazo!in-2-ytlamino}cyclohexyl)methyllurea 597 (M + H) 1
2491 N-(2,6-dichlorophenyI)-Nt-[(cis-4-{[4-(dimethy!amino)-5J6J7,8-
tetrahydroquinazolin-2-yllamino)cyc!ohexyl)methyI]urea 491 (M + H) 1
2492 N-[(cis-4-{[4-(dimethyIamtno)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexy!)methyl]-Nf-(2-methoxy-5-methyIphenyl)-
urea 467 (M + H) -i
2493 N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyC1-5hexyI)methyI]-Nt-(2-methyI-6-nitrophenyl)urea 482 (M + H) 3

483

Ex. No. compound name MS class
2494 N-(3,4-difluorophenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazo]in-2-yI]amino}cYclohexyl)methyilurea 459 (M + H)
2495 N-(3,5-difluorophenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-ynamino}cyclohexyl)methyl]urea 459 (M + H) 3
2496 N-(3-chIoro-4-fluorophenyl)-N'-[(cis-4-{[4-(dimethy)amino)-
5,6,7,8-tetrahydroquinazolin-2-yIlamino}cyC1-5hexyI)methyl]urea 475 (M + H)

484
Example 2497
2r3,4-Tritluoro-Ar-{m-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}-benzamide
trifluoroacetate
Step A: Synthesis of cis-(4-ter^butoxycarbonylamino-cyclohexyl)-carbamic acid benzyl ester.
To a solution of ds-(4-amino-cyclohexyl)-carbamic acid /er/-butyl ester (4 g, 0.019 mol) in
50 mL CH2C12 was added DIEA (4.9 mL, 0.028 mol). The solution was cooled on an ice bath and
CbzCl (2.9 mL, 0.020 mol) was added slowly. The solution was removed from the ice bath and
stirring continued for an additional hour. The solvent was evaporated and the material was
subjected to chromatography (0-40% ethyl acetate in hexanes) to yield cis-(4-tert-
butoxycarbonylamino-cyclohexyl)-carbamic acid benzyl ester (6.2 g, 0.018 mol, 95%) as a white
solid.
ESI MS m/e 349.0 M + H+; lH NMR (400 MHz, DMSO-d6) 6 7.34-7.28 (m, 5 H), 7.12 (d, J= 5.6
Hz, 1 H), 6.62 (brs, 1 H), 4.98 (s, 2 H), 3.39-3.37 (m, 2 H), 1.60-1.45 (m, 8 H), 1.37 (s, 9 H).
Step B: Synthesis of c/s-(4-amino-cyclohexyl)-carbamic acid benzyl ester.
To a solution of ds-(4-te^butoxycarbonylamino-cyC1-5hexyl)-carbamic acid benzyl ester
(6.2 g, 0.018 mol) in 40 mL CH2C12 was added TFA (2.7 mL, 0.36 mol). The solution was stirred
at room temperature for 4 hours. The excess solvent was evaporated off and the resulting oil was
dissolved in 30 mL CH2C12. The organic layer was extracted with 30 mL of a dilute NaOH (aq) /
NaHCO3 (aq) solution. The aqueous layer was back extracted twice with CH2C12 and the organic
layers combined, dried over MgSC>4, and concentrated to yield c/s-(4-amino-cyclohexyl)-carbamic
acid benzyl ester (4.3 g, 97%) as a colorless oil. The oil was carried forward without further
purification.
ESI MS m/e 249.2 M + H+.

485
Step C: Synthesis of c/s-[4-(4-methyi-quinolin-2-ylaniino)-cyclohexyl]-carbamic acid benzyl
ester.
To a solution of c/s-(4-amino-cyC1-5hexyl)-carbamic acid benzyl ester (0.5 g, 0.0020 mol)
in 1 mL 2-propanol was added 2-chloro-4-methyI-quinoline (0.43 g, 0.0024 mol) and IEA (526 uL,
0.0030 mol). The mixture was heated in a microwave synthesizer at 170 °C for 5 hours. The
reaction was repeated 7 more times (4 g total material) and the reaction mixtures were pooled. The
solvent was evaporated and the material subjected to chromatography (2-4 % 2M NH3 in MeOH /
CH2C12) to yield cw-[4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-carbarnic acid benzyl ester (3.3
g, 53%) as a colorless oil.
ESI MS m/e 390.2 M + H" ; *H NMR (400 MHz, DMSO-d6) 5 7.71 (d, J= 8 Hz, 1 H), 7.46-7.39
(m, 2 H), 7.37-7.19 (m, 7 H), 6.68 (m, 2 H), 5.01 (s, 2 H), 4.07 (m, 1 H), 3.46 (m, 1 H), 2.44 (s, 3
H), 1.79-1.71 (m,2H), 1.70-1.59 (m, 6 H).
Step D: Synthesis of c/s-A^-methyl-quinolin^-yty-cyclohexane-l^-diamine.
To a solution of c/s-[4-(4-methyl-quinoiin-2-ylamino)-cyclohexyl]-carbaniic acid benzyl
ester (3.3 g, 0.0085 mol) in 200 mL EtOH was added 10% Pd/C (330 mg). The reaction mixture
was stirred at room temperature under H2(g) atmosphere for 3 hours. The H?(g) atmosphere was
removed and the mixture was through a pad of celite and washed with ethyl acetate. The solvent
was concentrated and the material was subjected to chromatography (2-4 % 2M NH3 in MeOH /
CH2CI2) to yield cz5-Ar-(4-methyl-quinolin-2-y!)-cyclohexane-l,4-diamine (2.0 g, 92%) as a light
brown solid.
ESI MS m/e 256.4 M + H+ ; !H NMR (400 MHz, DMSO-d6) 5 7.71 (d, J= 8 Hz, 1 H), 7.46-7.39
(m, 2 H), 7.14-7.10 (m, 1 H), 6.69-6.68 (m, 2 H), 4.07-4.05 (m, 1 H), 2.81-2.77 (m, 1 H), 2.44 (s, 3
H), 1.78-1.71 (m,2H), 1.62-1.40 (m, 6 H).

486
Step E: Synthesis of 2^,4-trifluoro-Ar-{c/s-4-[(4-methylquinoIin-2-yl)amino]cyclohexyI}-
benzamide trifluoroacetate.
To a solution of d5-Af-(4-methyl-quinolin-2-yl)-cyclohexane-l,4-diamine (23 mg, 0.090
mmol) in 0.5 mL DMF was added pyridine (12 uL, 0.15 mmol) and 2,3,4-trifluorobenzoyl chloride
(12.8 uL, 0.10 mmol). The reaction mixture was stirred overnight and then 0.5 mL of DMSO was
added to the mixture. The compound was then subjected to purification by prep LC1-5S to yield
2,3,4-trifluoro-Ar-{c/5-4-[(4-methylquinolin-2-yI)amino]cyclohexyl}-benzamide trifluoroacetate
(10.1 mg, 21%) as a white solid.
ESI MS m/e 414.2 M + IT ; 'H NMR (400 MHz, DMSO-d6) 5 12.44 (brs, 1 H), 9.27 (brs, 1 H),
8.45 (d, J= 6.4 Hz, 1 H), 7.98-7.93 (m, 2 H), 7.80 (t, J= 7.6 Hz , 1 H), 7.53 (t, J= 8.0 Hz , 1 H),
7.43-7.37 (m, 2 H), 7.01 (s, 1 H), 4.05 (m, 1 H),3.97(m, 1 H), 2.69 (s, 3 H), 1.86-1.74 (m, 8 H).
Example 2498
3,4-Difluoro-7V-{c/$-4-[(4-methylquinoIin-2-yl)amino]cyc)ohexyl}benzamide trifluoroacetate
StepA: Synthesis of 3y4-difluoro-A^cw-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}-
benzamide trifluoroacetate
Using the procedure of step E of example 2497, the title compound was obtained.
ESI MS m/e 396.18 M + H* ; 'H NMR (400 MHz, DMSO-d6) 8 12.40 (brs, 1 H), 9.25 (brs, 1 H),
8.33 (d, J = 6.0 Hz , 1 H), 7.98-7.90 (m, 3 H), 7.80-7.76 (m, 2 H), 7.58-7.50 (m, 2 H), 7.02 (brs, I
H), 4.09 (m, 1 H), 3.94 (m, 1 H), 2.61 (s, 3 H), 1.84-1.74 (m, 8 H).
Example 2499
4-Cyano-iV-{c/y-4-[(4-methylquinoHn-2-yI)amino]cyclohexyl}benzamide trifluoroacetate

487
Step A: Synthesis of 4-cyano-7V-{cw-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}benzamide
trifluoroacetate.
Using the procedure of step E of example 2497, the title compound was obtained.
ESI MS m/e 385.2 M + H+ ; *H NMR (400 MHz, DMSO-d6) 5 12.38 (brs, I H), 9.27 (brs, 1 H),
8.51 (d, 7=6.0 Hz, 1 H), 8.01-7.95 (m, 6H), 7.80 (t, 7= 7.2 Hz , 1 H), 7.54 (t, 7 = 8.0 Hz , 1 H),
7.02 (brs, 1 H), 4.09 (m, 1 H), 3.96 (m, 1 H), 2.66 (s, 3 H), 1.85-1.75 (m, 8 H).
Example 2500
3-Fluoro-Ar-{c«-4-[(4-methyIquinolin-2-yl)ainino]cyC1-5hexyl}benzamide trifluoroacetate
Step A: Synthesis of 3-fluoro-iV-{cw-4-[(4-methyIquinolin-2-yl)amino]cyclohexyl}benzamide
trifluoroacetate.
Using the procedure of step E of example 2497, the title compound was obtained.
ESI m/e 378 M + H"; 'H NMR (400 MHz, DMSO-d6) 5 12.38 (brs, 1 H), 9.25 (brs, 1 H), 8.33 (d, 7
= 6.0 Hz , 1 H), 7.98-7.91 (m, 2 H), 7.80 (t, 7- 7.6 Hz , 1 H), 7.71-7.64 (m, 2 H), 7.55-7.49 (m, 2
H), 7.41-7.36 (m, 1 H), 4.12 (m, 1 H), 4.08 (m, 1 H), 2.77 (s, 3 H), 1.85-1.74 (m, 8 H).
Example 2501
3,5-Difluoro-Ar-{c«-4-[(4-methylquinolin-2-yI)aminolcyclohexyl}benzamide trifluoroacetate
Step A: Synthesis of 3,5-difluoro-7V-{c«-4-[(4-methyIquinoIin-2-yl)amino]cyC1-5hexyI}-
benzamide trifluoroacetate.
Using the procedure of step E of example 2497, the title compound was obtained.
ESI MS m/e 396 M + Yf ; !H NMR (400 MHz, DMSO-d6) 8 12.40 (brs, 1 H), 9.25 (brs, 1 H), 8.40
(d, 7= 6.0 Hz , 1 H), 7.98-7.96 (m, 2 H), 7.80 (t, 7- 7.2 Hz , 1 H), 7.59-7.44 (m, 4 H), 7.02 (brs, 1
H),4.09(m, 1 H),3.94(m, 1 H), 2.68 (s, 3 H), 1.85-1.74 (m, 8 H).

488
Example 2502
Ar-{m-4-((4-MethyIquinoIin-2-yl)aminolcyclohexyl}-2-[4-(trifluoromethoxy)phenoxy]-
acetamide trifluoroacetate
Step A: Synthesis of 7V-{ci.s-4-[(4-methylquinolin-2-yl)amino]cyC1-5hexyl}-2-[4-
(trifluoromethoxy)phenoxy]-acetamide trifluoroacetate.
To a solution of c/s-A^-methyl-quinolin^-ylJ-cyclohexane-l^-diamine (25.5 mg, 0.1
mmol) in 0.5 mL DMF was added 4-(trifluoromethoxy)phenoxyacetic acid (23.6 mg, 0.1 mmol),
DIEA (0.026 mL, 0.15 mmol), and HATU (45.6 mg, 0.12 mmol). The reaction mixture was stirred
overnight and then 0.5 mL of DMSO was added to the mixture. The compound was then subjected
to purification by prep LC1-5S to yield A^{c/s-4-[(4-methylquinolin-2-yl)amino]cyC1-5hexyl}-2-[4-
(trifluoromethoxy)phenoxy]-acetamide trifluoroacetate (22.3 mg, 38%) as a white solid.
ESI MS m/e 474.4 M + H+ ; ]H NMR (400 MHz, DMSO-d6) 5 12.47 (s, 1 H), 9.25 (s, 1 H), 8.00-
7.92 (m, 3 H), 7.80 (t, J= 7.2 Hz, 1 H), 7.53 (t, J = 8.0 Hz, 1 H), 7.31 (d, J- 8.8 Hz, 2 H), 7.04-
7.01 (m, 3 H), 4.55 (s, 2 H), 4.06 (m, 1 H), 3.84 (m, 1 H), 2.69 (s, 3 H), 1.78-1.68 (m, 8 H).
Example 2503
2-(3,4-Difluorophenyl)-7V-{c/5-4-[(4-methylquinolin-2-yI)amino]cyclohexyl}acetamide
trifluoroacetate
Step A: Synthesis of 2-(3,4-difluorophenyI)-7V-{c/5-4-[(4-methylquinolin-2-
yl)amino]cyclohexyljacetamide trifluoroacetate.
Using the procedure of step A of example 2502, the title compound was obtained.
ESI MS m/e 410 M + H+ ; 'H NMR (400 MHz, DMSO-d6) 8 12.42 (brs, 1 H), 9.26 (brs, 1 H), 8.09
(d, J= 6.4 Hz, 1 H), 7.98-7.92 (m, 2 H), 7.80 (t, J= 7.6 Hz, 1 H), 7.54 (t, J= 8.8 Hz, 1 H), 7.38-

489
7.27 (m, 2 H), 7.10-7.07 (m, 1 H), 7.01 (brs, 1 H), 4.02 (m, 1 H),3.94(m, 1 H),2.61 (s,3H), 1.79-
1.69 (m, 8 H).
Example 2504
2-(2-Bromo-4,5-dimethoxyphenyl)-iV-{cw-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}-
acetamide trifluoroacetate
Step A: Synthesis of 2-(2-bromo-4,5-dimethoxyphenyl)-iV-{ctf-4-[(4-methyIquinolin-2-
yl)amino]cyclohexyl}acetamide trifluoroacetate.
Using the procedure of step A of example 2502, the title compound was obtained.
ESI MS m/e 512.2 M + FT ; ]H NMR (400 MHz, DMSO-d6) 5 12.45 (brs, 1 H), 9.25 (brs, 1 H),
8.00-7.92 (m, 3 H), 7.80 (t, J = 7.6 Hz , 1 H), 7.53 (t, J= 7.6 Hz , 1 H), 7.09 (s, 1 H), 7.01 (brs, 1
H), 6.95 (s, 1 H), 4.10 (m, 1 H), 3.78 (m, 1 H), 3.74 (s, 3 H), 3.72 (s, 3 H), 3.53 (s, 2 H), 2.69 (s, 3
H), 1.78-1.67 (m, 8 H).
Example 2505
4-(BenzyIoxy)-Ar-{c/s-4-[(4-methylquinolin-2-yl)amino)cyclohexyl}benzamide trifluoroacetate
Step A: Synthesis of 4-(benzyloxy)-Ar-{c/$-4-[(4-methyIquinolin-2-yl)amino]cyC1-5hexyl}-
benzamide trifluoroacetate.
Using the procedure of step A of example 2502, the title compound was obtained.
ESI MS m/e 466.2 M + rT; !H NMR (400 MHz, DMSO-d6) 5 12.39 (brs, 1 H), 9.25 (brs, 1 H),
8.06 (d, J= 6.0 Hz , 1 H), 7.98-7.96 (m, 2 H), 7.84-7.76 (m, 3 H), 7.54 (t, J= 8.0 Hz , 1 H), 7.46 (d,
J= 7.2 Hz , 2 H), 7.41 (t, J= 12 Hz , 2 H), 7.35-7.31 (m, 1 H), 7.08 (d, J= 8.8 Hz, 2 H), 7.02 (brs,
1 H), 5.17 (s, 2 H), 4.09 (m, 1 H), 3.93 (m, 1 H), 2.66 (s, 3 H), 1.84-1.72 (m, 8 H).

490
Example 2506
2-(2-Methoxyphenoxy)-iV-{cw-4-[(4-iiiethyIquinolin-2-yl)ainino]cyclohexyl}acetainide
trifluoroacetate
Step A: Synthesis of 2-(2-methoxyphenoxy)-A'r-{c/5-4-[(4-methylquinolin-2-
yl)amino]cyclohexyl}acetamide trifluoroacetate.
Using the procedure of step A of example 2502, the title compound was obtained.
ESI MS m/e 420.2 M + H+ ; !H NMR (400 MHz, DMSO-d6) 5 12.50 (brs, 1 H), 9.25 (brs, 1 H),
7.98-7.93 (m, 2 H), 7.80-7.76 (m, 2 H), 7.53 (t, J = 5.6 Hz, 1 H), 7.02-6.85 (m, 5 H), 4.50 (s, 2 H),
4.07 (m, 1 H), 3.85 (m, 1 H), 3.79 (s, 3 H), 2.61 (s, 3 H), 1.84-1.69 (m, 8 H).
Example 2507
2-(4-Fluorophenoxy)-jV-{c/5-4-f(4-methyIquinolin-2-yl)amino]cyclohexyl}nicotinamide
trill u oroacetate
Step A: Synthesis of 2-(4-fluon>phenoxy)-iV-{cK-4-[(4-methylquinolin-2-
yl)amino]cyclohexyl}nicotinamide trifluoroacetate.
Using the procedure of step A of example 2502, the title compound was obtained.
ESI MS m/e 471.4 M + H+ ; ]H NMR (400 MHz, CD3OD) 5 8.29 (dd, J= 7.6, 2.0 Hz, I H), 8.19
(dd,J=4.8,2.0Hz, 1 H), 8.01( d, J= 8.0 Hz, 1 H), 7.88 (brs, 1 H), 7.80 (t,J = 8.4 Hz, 1 H), 7.57
(t, J= 8.0 Hz, 1 H), 7.25-7.15 (m, 5 H), 6.90 (brs, 1 H), 4.20 (brs, 1 H), 4.07 (brs, 1H), 2.67 (s,
3H), 2.02-1.81 (m, 8H).

491
Example 2508
2-(4-ChIorophenoxy)-Ar-{m-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}nicotinamide
trifluoroacetate
Step A: Synthesis of 2-(4-Chlorophenoxy)-iV-{C1-5-4-[(4-methylquinolin-2-
yl)amino]cyclohe\yl}nicotinamide trifluoroacetate.
Using the procedure of step A of example 2502, the title compound was obtained.
ESI MS m/e 487.2 M + H+; 'HNMR (400 MHz, DMSO-d6) 5 13.0 (brs, 1 H), 9.50 (d, J= 6.8 Hz,
1 H), 8.35 (m, 1 H), 8.19 (m, 1 H), 8.07 (d, J= 6.8 Hz, 1 H), 7.93 (d, J= 7.6 Hz, 1 H), 7.75 (t, J =
7.2 Hz, 1 H), 7.50 (m, 3 H), 7.30 (m, 3 H), 7.10 (brs, 1 H), 4.38 (brs, 1 H), 4.01 (brs, 1 H), 2.57 (s,
3H), 1.83 (m,8H).
Example 2509
2,6-Dimethoxy-iV-{c«-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}nicotinamide
trifluoroacetate
Step A: Synthesis of 2,6-dimethoxy-Ar-{cw-4-[(4-methyIquinolin-2-
yl)amino]cyclohexyl}nicotinamide trifluoroacetate.
Using the procedure of step A of example 2502, the title compound was obtained.
ESI MS m/e 421.2 M + H+ ; ]H NMR (400 MHz, DMSO-d6) 5 13.1 (brs, 1 H), 9.74 (d, J= 8.0 Hz,
1 H), 8.30(d,J=8.4Hz, 1 H), 8.17 (d, J= 8.4 Hz, 1 H), 7.98 (m, 2 H), 7.60 (m, 1 H), 7.50 (t, J =
7.6 Hz, 1 H), 7.19 (brs, 1 H), 4.43 (brs, 1H), 3.94 (brs, 7H), 2.58 (s, 3H), 1.90 (m, 8 H).
Example 2510
cw-Ar-[4-Bromo-2-(trifluoromethoxy)benzyI]-A^-(4-methylquinolin-2-yl)cyclohexane-l,4-
diamine bis-trifluoroacetate

492
Step A: Synthesis of m-AL[4-bromo-2-(trifluoromethoxy)benzyl]-Af'-(4-methyIquinoIin-2-
yl)cyclohexane-l,4-diaminebis-trifluoroacetate.
To a solution of c/s-A^-methyl-quinolin^-yO-cyclohexane-l^-diamine (25.5 mg, 0.1
mmol) in 0.5 mL MeOH was added 4-bromo-2-trifluoromethoxybenzaldehyde (26.9 mg, 0.1
mmol). The reaction mixture was stirred for a half hour and then sodium triacetoxyborohydride
(84.8 mg, 0.4 mmol) was added to the reaction. The mixture was stirred overnight and then 0.5 mL
of DMSO was added. The compound was then subjected to purification by prep LC1-5S to yield
c/,s-Ar-[4-bromo-2-(trifluoromethoxy)ben2yl]-iV-(4-methylquinolin-2-yl)cyclohexane-l,4-diamine
bis-trifluoroacetate (9.6 mg, 13%) as a white solid.
ESI MS m/e 508.0 M + H"; ]H NMR (400 MHz, CD3OD) 6 8.04 (d, J= 8.0 Hz, 1H), 7.84 (brs, 1
H), 7.81 (t, J= 7.2 Hz, 1 H), 7.69-7.63 (m, 3 H), 7.58 (t, J= 8.0 Hz, 1 H), 7.16 (brs, 1 H), 4.36 (s, 2
H), 4.26 (m, 1 H), 3.32-3.30 (m, 1 H), 2.71 (s, 2 H), 2.66 (s, 3 H), 2.16-1.93 (m, 8 H).
Example 2511
m-7V-[(5-Bromo-lH-indol-3-yl)methyll-A^-(4-methylquinoliii-2-yl)cyclohexane-l,4-diamine
bis-trifluoroaeetate
Step A: Synthesis of c/s-7V-[(5-bromo-lH-indol-3-yl)methyl]-A^-(4-methylquinolin-2-
yl)cyclohexane-l,4-diamine bis-trifluoroacetate.
Using the procedure of step A of example 2510, the title compound was obtained.
ESI MS m/e 463.2 M + H" ; !H NMR (400 MHz, CD3OD) 5 8.03 (d,J= 8.0 Hz, 1 H), 7.92 (s, 1
H), 7.87 (brs, 1 H), 7.80-7.76 (t, J= 7.2 Hz, 1 H), 7.57-7.53 (m, 2 H), 7.38 (d, J= 8.8 Hz, 1 H),
7.31 (d, J= 8.4 Hz, 1 H), 7.14 (brs, I H), 4.47 (s, 2 H), 4.23 (m, 1 H), 3.37 (m, 1 H), 2.71 (brs, 2 H),
2.65 (s, 3 H), 2.15-1.91 (m, 8 H).

493
Example 2512
c/5-7V-(3,5-Dimethoxybenzyl)-Af'-(4-methylquinolin-2-yl)cyclohexane-l,4-diainine bis-
trifluoroacetate
Step A: Synthesis of as-7V~(3,5-dimethoxybenzyI)-A^-(4-methylquinolin-2-yl)cydohexane-l,4-
diamine bis-trifluoroacetate.
Using the procedure of step A of example 2510, the title compound was obtained.
ESI MS m/e 406.2 M + *T ; 'H NMR (400 MHz, CD3OD) 5 8.03 (d, J = 8.0 Hz, 1 H), 7.88 (brs, 1
H), 7.80 (t, J= 7.2 Hz, 1 H), 7.57 (t, J = 8.4 Hz, 1 H), 7.17 (brs, 1 H), 6.71 (s, 2 H); 6.55 (s, 1 H),
4.24 (m, 1 H), 4.21 (s, 2 H), 3.81 (s, 6 H), 3.35 (m, 1 H), 2.70 (brs, 2 H), 2.66 (s, 3 H), 2.14-1.90
(m, 8 H).
Example 2513
c«-A'-(3,5-Dichlorobenzyl)-Ar'-(4-methylquinoliii-2-yl)cyclohexane-l,4-diainine bis-
trifluoroacetate
Step A: Synthesis of C1-5-iV-(3,5-dichlorobenzyl)-7V-(4-methylquinolin-2-yl)cyC1-5hexane-l,4-
diamine bis-trifluoroacetate.
Using the procedure of step A of example 2510, the title compound was obtained.
ESI MS m/e 414.2 M + H+; 'H NMR (400 MHz, CD3OD) 8 8.04 (d, J= 8.4 Hz, 1 H), 7.86 (brs, 1
H), 7.81 (t, J= 12 Hz, 1 H), 7.58-7.54 (m, 4 H), 7.16 (brs, 1 H), 4.30 (s, 2 H), 4.25 (m, 1 H), 3.41
(m, 1 H), 2.76 (brs, 2 H), 2.66 (s, 3 H), 2.12-1.92 (m, 8 H).
Example 2514
C1-5-iV-(3,4-Difluorobenzyl)-jV-(4-methylquinolin-2-yl)cyclohexane-l,4-diamine bis-
trifluoroacetate

494
Step A: Synthesis of cw-Ar-(3,4-difIuorobenzyl)-A'?-(4-methylquinoUn-2-yl)cyclohexane-l,4-
diamine bis-trifluoroacetate.
Using the procedure of step A of example 2510, the title compound was obtained.
ESI MS m/e 382.2 M + H+; *H NMR (400 MHz, CD3OD) 5 8.03 (d, J = 8.0 Hz, 1 H), 7.86 (brs, 1
H), 7.80 (t, J= 7.2 Hz, 1 H), 7.57-7.51 (m, 2 H), 7.39-7.37 (m, 2 H), 7.16 (brs, 1 H), 4.29 (s, 2 H),
4.25 (m, 1 H), 3.37 (m, 1 H), 2.71 (brs, 2 H), 2.66 (s, 3 H), 2.11-1.95 (m, 8 H).
Example 2515
AL(3,5-DifluorophenyI)-A^-{m-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}urea
trifluoroacetate
Step A: Synthesis of Ar-(3^-difluorophenyl)-7V-{c/s-4-[(4-methylquinolin-2-
yl)amino]cyclohexyl}urea trifluoroacetate.
To a solution of c/5-Ar-(4-methyl-quinolin-2-yl)-cyclohexane-l,4-diamine (20 mg, 0.078
mmol) in 0.5 mL of DMSO was added 3,5-difluorophenyl isocyanate (9.3 uL, 0.078 mmol). The
reaction mixture was stirred overnight and then 0.5 mL of DMSO was added to the mixture. The
compound was then subjected to purification by prep LC1-5S to yield Ar-(3,5-difluorophenyl)-A^1-
{c/s-4-[(4-methylquinolm-2-yl)amino]cyclohexyI}urea trifluoroacetate (12 mg, 29%) as a white
soIid.ESI MS m/e 411.2 M + H+ ; 'H NMR (400 MHz, CD3OD) 5 8.02 (d, J= 8.0 Hz, 1 H), 7.87
(brs, 1 H), 7.80 (t, J= 7.6 Hz, 1 H), 7.56 (t, J= 1.6 Hz, 1 H), 7.07 (s, 1 H), 7.03 (s, 1 H), 6.97 (brs,
1 H), 6.50 (t, ./= 9.2 Hz, 1 H), 4.02 (m, 1 H), 3.89 (m, 1 H), 2.68 (brs, 3 H), 2.66 (s, 3 H), 1.99-
1.78 (m, 8 H).

495
Example 2516
Ar-[3,5-Bis(trifluoromethyl)phenyl]-AfT-{c/.$-4-{(4-methylquinolin-2-yi)aniino]cyclohexyI}urea
trifluoroacetate
Step A: Synthesis of 7V-[3,5-bis(trifluoromethyl)phenyl]-A"-{C1-5-4-{(4-methylquinoIin-2-
yl)amino]cyclohexyl}urea trifluoroacetate.
Using the procedure of step A of example 2515, the title compound was obtained.
ESI MS m/e 511.2 M + HVH NMR (400 MHz, CD3OD) 5 8.02 (s, 2 H), 8.00 (s, 1 H), 7.87 (brs,
1 H), 7.80 (t, J= 12 Hz, 1 H), 7.57 (t, J= 8.0 Hz, 1 H), 7.49 (s, 1 H), 6.98 (brs, 1 H), 4.04 (m, 1 H),
3.91 (m, 1 H), 2.69 (brs, 3 H), 2.66 (s, 3 H), 2.01-1.80 (m, 8 H).
Example 2517
Ar-(3-Chlorophenyl)-7V-{c«r-4-[(4~methylquinoIin-2-yl)amino]cyclohexyl}urea trifluoroacetate
Step A: Synthesis of iV-(3-chlorophenyl)-A??-{cw-4-[(4-methylquinolin-2-
yl)amino]cyclohexyl}urea trifluoroacetate.
Using the procedure of step A of example 2515, the title compound was obtained.
ESI MS m/e 409.2 M + it; 'H NMR (400 MHz, CD3OD) 5 8.00 (d, J = 8.4 Hz, I H), 7.87 (brs, 1
H), 7.79 (t, J= 7.6 Hz, 1 H), 7.59 (s, I H), 7.56 (t,J= 7.6 Hz, 1 H), 7.21-7.15 (m, 2 H), 6.96 (brs, 1
H), 6.93-6.91 (m, 1 H), 4.01 (m, 1 H), 3.89 (t, 1 H), 2.66 (brs, 6 H), 1.99-1.78 (m, 8 H).
Example 2518
^-(S^-DichlorophenylJ-A^-Jc/s^-K^methylquinolin^-y^aminoJcyclohexylJurea
trifluoroacetate

496
Step A: Synthesis of Ar-(3,4-dichlorophenyl)-A^-{cw-4-[(4-methylquinolin-2-
yl)amino]cyclohexyl}urea trifluoroacetate.
Using the procedure of step A of example 2515, the title compound was obtained.
ESI MS m/e 443.2 M+H+ ; !H NMR (400 MHz, CD3OD) 6 8.00 (d, J= 7.6 Hz, 1 H), 7.87 (brs, 1
H), 7.79-7.74 (m, 2 H), 7.56 (t, J= 7.6 Hz, 1 H), 7.34 (d, J = 8.4 Hz, 1 H), 7.20 (d, J= 8.4 Hz, 1 H),
6.97 (brs, 1 H), 4.02 (m, 1 H), 3.88 (m, 1 H), 2.66 (brs, 6 H), 1.98-1.78 (m, 8 H).
Example 2519
Ar-(3-Methoxyphenyl)-iV-{ci5-4-[(4-methylquinolin-2-yl)amino]cyclohexyI}urea
trifluoroacetate
Step A: Synthesis of Ar-(3-methoxyphenyl)-A"-{c«-4-[(4-methylquinolin-2-yl)amino]
cyclohexyljurea trifluoroacetate.
Using the procedure of step A of example 2515, the title compound was obtained.
ESI MS m/e 405.4 M + HVH NMR (400 MHz, CD3OD) 5 8.00 (d, J= 8.0 Hz, 1 H), 7.87 (brs, 1
H), 7.79 (t, J= 7.6 Hz, 1 H), 7.56 (t, J= 8.0 Hz, 1 H), 7.14-7.10 (m, 2 H), 6.96 (brs, 1 H), 6.84 (d, J
= 8.0 Hz, 1 H), 6.53 (d, J= 8.4 Hz, 1 H), 4.01 (m, 1 H), 3.89 (m, I H), 3.75 (s, 3 H), 2.71 (brs, 6 H),
1.99-1.78 (m, 8 H).
Example 2520
3-Methoxy-iV-[c/s-4-(quinolin-2-ylamino)cyclohexyl]benzamide trifluoroacetate
Step A: Synthesis of cis-[4-(3-methoxy-benzoylamino)-cyC1-5hexyl]-carbamic acid tert-hutyX
ester.
To a solution of c«-(4-amino-cyclohexy!)-carbamic acid /er/-butyl ester (2.8 g, 0.013 mol)
in 40 mL CH2C12 stirring on ice was added DIEA (3.41 mL, 0.020 mol). The solution was cooled

497
on an ice bath and m-anisoyl chloride (1.84 mL, 0.013 mol) was added slowly. The solution was
removed from the ice bath and stirring continued for an additional hour. The solvent was
evaporated and the material was subjected to chromatography (0-40% ethyl acetate in hexanes) to
yield m-[4-(3-methoxy-benzoylamino)-cyclohexyl]-carbamic acid f erf-butyl ester (4.3 g, 94 %) as
a white solid.
ESI MS m/e 349.0 M + H"; !H NMR (400 MHz, DMSO-d6) 5 8.03 (d, J = 6.8 Hz, 1 H), 7.42-7.32
(m, 3 H), 7.07 (6d,J= 8.4, 2.4 Hz, 1H), 6.62 (brs, 1 H), 3.79 (s, 3 H), 3.77 (m, 1 H), 3.41 (m, 1 H),
1.71-1.70 (m, 4 H), 1.52-1.46 (m, 4 H), 1.38 (s,9H).
Step B: Synthesis of c/s-7V-(4-amino-cyC1-5hexyl)-3-methoxy-benzamide.
To a solution of c/s-[4-(3-methoxy-benzoylamino)-cyclohexyl]-carbamic acid tert-butyl
ester (4.3 g, 0.012 mol) in 50 mL CH2C12 was added TFA (1.84 mL, 0.024 mol). The solution was
stirred for 4 hours and the solvent evaporated. The resulting oil was re-dissolved in 50 mL CH2C1?.
The organic layer was extracted with 50 mL of a dilute NaOH (aq) / NaHCC>3 (aq) solution. The
aqueous layer was extracted twice more with CH2CI2 and the organic layers combined, dried over
MgSO4, and concentrated. The resulting precipitate was crystallized in ether and hexanes to yield
cw-A^-(4-amino-cyclohexyl)-3-methoxy-benzamide (2.4g, 78%) as a white solid.
ESI MS m/e 249.0 M + FT ; 'H NMR (400 MHz, DMSO-d6) 5 8.10 (d, J= 7.2 Hz, 1 H), 7.42-7.32
(m, 3 H), 7.07 (dd, J= 8.0, 2.4 Hz, 1 H), 3.79 (brs, 4 H), 2.91 (m, 1 H), 1.80-1.74 (m, 2 H), 1.52-
1.46 (m, 6H), 1.31 (brs, 2 H).
Step C: Synthesis of 3-methoxy-iV-[c/s-4-(quinolin-2-ylamino)cyclohexyl]benzamide
trifluoroacetate.
To a solution of cw-Ar-(4-amino-cyclohexyl)-3-methoxy-benzamide (28.4 mg, 0.1 mmol) in
0.5 mL 2-propanol was added 2-chIoroquinoline (32.7 mg, 0.2 mmol) and DIEA (34.8 uL, 0.2
mmol). The reaction mixture was heated in a microwave synthesizer at 170 °C for 10 hours. The
solvent was removed and the resulting oil dissolved in 1 mL of DMSO. The compound was then

498
subject to purification by prep LC1-5S to yield 3-methoxy-Af-[c/s-4-(quinolin-2-
ylamino)cyclohexyl]benzamide trifluoroacetate (26 mg, 53%) as a colorless oil.
ESI MS m/e 376.2 M + H+; !H NMR (400 MHz, CD3OD) 6 7.85 (d, J= 9.2 Hz, 1 H), 7.62 (t, J =
8.8 Hz, 2 H), 7.50 (t, J= 7.2 Hz, 1 H), 7.39-7.36 (m, 3 H), 7.19 (t, J= 12 Hz, 1 H), 7.10-7.07 (m,
1 H), 6.82 (d, J= 9.2 Hz, I H), 4.18 (m, 1 H), 4.02 (m, 1 H), 3.84 (s, 3 H), 1.95-1.22 (m, 1 H).
Example 2521
S-methoxy-^^cw-^JI^ttrifluoromethy^quinoIin-l-yllaminoJcyclohexy^benzamide
trifluoroacetate
Step A: Synthesis of 2-chloro-4-trifluoromethyl-quinoline.
To a solution of 4-triftuoromethyl-quinolin-2-ol (1.01 g, 0.0047 mol) in 10 mL POCI3 was
added N, iV-dimethylaniline (661 uL, 0.0052 mol). The mixture was heated to reflux (125 °C) and
stirred for 4 hours until the starting material completely dissolved and the solution turned dark
purple in color. The solution was then cooled and poured slowly on ice (30 g; caution highly
exothermic) to quench the reaction. The aqueous layer was then extracted three times with CH2C12
(25 mL). The organic layer was dried with MgSO,*, concentrated, and subjected to purification by
chromatography (100% CH2C12) to yield 2-chloro-4-trifluoromethyl-quinoIine (823 mg, 75%) as a
slightly yellow solid.
ESI MS m/e 232.0 M + rT ; *H NMR (400 MHz, DMSO-d6) 8 8.15-8.09 (m, 2 H), 8.06 (s, 1 H),
8.01-7.97 (m, I H), 7.88-7.85 (m, 1 H).
Step B: Synthesis of 3-methoxy-7V-(m-4-{[4-(trifluoromethyl)quinoIin-2-
yl]amino}cyclohexyl)benzamide trifluoroacetate.
To a solution of c/s-./V-(4-arnino-cyc]ohexyI)-3-methoxy-benzamide (50 mg, 0.20 mmol) in
0.5 mL 2-propanol was added 2-chloro-4-trifluoromethyl-quinoline (56 mg, 0.24 mmol), and DIEA
(52.6 uL, 0.30 mmol). The reaction mixture was heated in a microwave synthesizer at 170° C for 5

499
hours. The solvent was removed and the resulting oil dissolved in 1 mLof DMSO. The compound
was then subjected to purification by prep LC1-5S to yield 3-methoxy-JV-(c/5-4-{[4-
(trifluoromethyi)quinolin-2-yl]amino}cyclohexyI)benzamide trifluoroacetate (71.8 nig, 64%) as a
white solid.
ESI MS m/e 444.4 M + H+ ; 'H NMR (400 MHz, DMSO-d6) 5 8.22 (d, J= 6.4 Hz, 1 H), 7.79-7.77
(m, 2 H), 7.69 (m, 1 H), 7.50 (s, 1 H), 7.44-7.34 (m, 4 H), 7.09 (dd,y= 8.0, 2.4 Hz I H), 4.14 (m, 1
H), 3.87 (m, 1 H), 3.80 (s, 3 H), 1.94-1.92 (m, 2 H), 1.82-1.72 (m, 6 H).
Example 2522
3-Methoxy-7V-{C1-5-4-[(quinolin-2-ylmethyl)amino]cyclohexyl}benzamide trifluoroacetate
Step A: Synthesis of 3-methoxy-Ar-{c/$-4-[(quinolin-2-ylmethyl)amino]cyclohexyl}benzamide
trifluoroacetate.
Using the procedure of step A of example 2510, the title compound was obtained.
ESI MS m/e 390.2 M + H+; 'H NMR (400 MHz, CD3OD) 8 8.41 (d, J= 8.8 Hz, 1 H), 8.14 (d, J =
8.4 Hz, 1 H), 7.99 (d, J= 8.0 Hz, 1 H), 7.84 (t, J= 7.2 Hz, 1 H), 7.67 (t, J= 7.2 Hz, 1 H), 7.55 (d, J
= 8.4 Hz, 1 H), 7.43-7.36 (m, 3 H), 7.12-7.10 (m, I H), 4.66 (s, 2 H), 4.13 (m, 1 H), 3.85 (s, 3 H),
3.46 (m, I H), 2.16-2.05 (m, 4 H), 2.05-1.96 (m, 2 H), 1.85-1.78 (m, 2 H).
Example 2523
Ar-(cw-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-4-methylbenzamide
trifluoroacetate
Step A: Synthesis of 2-chloro-4-dimethylamino-5-methylpyrimidine.
In 8 mL tetrahydrofuran was dissolved 2,4-dichloro-5-methylpyrimidine (0.5 g, 3.07
mmol) at 0 °C. To the reaction mixture was added dimethylamine (2M in methanol, 3.4 mL, 6.8

500
mmol) dropwise. The reaction mixture was stirred at 10 °C for 1.5 hour: do not increase the
reaction temperature. The solution was concentrated and purified by flash chromatography (silica
gel, 20% ethyl acetate and 5% methanol in hexanes) to give 2-chIoro-4-dimethylamino-5-
methylpyrimidine (307 rag, 58%) as a white solid.
ESI MS m/e 172 M+H+; lH NMR (400 MHz, CDCI3) 5 7.8 (s, 1 H), 3.18 (s, 6 H), 2.23 (s, 3 H).
Step B: Synthesis of c«-[4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexylj-carbamic acid tert-buty\ ester.
To a suspension of 2-chloro-4-dimethylamino-5-methylpyrimidine (250mg, 1.46 mmol) in
2-propanol (2.5 mL) was added c/s-(4-amino-cyC1-5hexyl)-carbamic acid /er/-butyl ester (340 mg,
1.60mmol) and DIEA (507 uL, 2.91 mmol). The reaction was performed in the Smith synthesizer
for 4.5 hours at 175° C. The solution was concentrated and purified by flash chromatography
(silica gel, 1% MeOH in CH2C12) to give c/s-[4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)
eyelohexyl]-carbarnic acid ter*-butyl ester (219 mg, 43 %) as a pale yellow solid.
ESI MS m/e 350.4 M + H+; ]H NMR (400 MHz, CDC13) 8 7.80 (s, 1 H), 4.6 (brs, 1 H), 3.94 (brs, 1
H), 3.60 (brs, 1 H), 3.02 (s, 6 H), 2.18 (s, 3 H), 1.85-1.70 (m, 8 H), 1.41 (s, 9 H).
Step C: Synthesis of c«-4-(4-dimethylamino-5-m ethyl-pyri mid in-2-y lam ino)-4-amino-
cyclohexane.
To a suspension of cJs-[4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino) cyclohexyl]-
carbamic acid tert-buXy\ ester (219 mg, 0.627 mmol) in DC1-5 (3 mL) was added trifluoroacetic acid
(2mL). The reaction stirred at room temperature for 2 hours and concentrated. A few drops
NaHCO3 was added, followed by 1M NaOH until the solution was basic. The product was
extracted with H2O and CH2CI2 three times. The organic layers were combined, dried over MgSO4,
filtered and concentrated to give c/5-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-4-
aminocyclohexane (115.9 mg, 74 %) as yellow oil.

501
ESI MS m/e 250.2 M + H+; 'H NMR (400 MHz, CDC13) 5 7.60 (s, 1 H), 4.95 (brs, 1 H), 3.90 (brs,
1 H), 2.98 (s, 6 H), 2.80 (brs, 1 H), 2.48 (brs, 2 H), 2.04 (s, 3 H), 1.78 (m, 2 H), 1.62 (m, 4 H), 1.4
(m, 2 H).
Step D: Synthesis of Ar-(c/s-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yJ]ainino}-
cyclohexyl)-4-m ethyl benzam id e trifluoroacetate.
To a suspension of c/5-4-(4-dimethyIamino-5-methy]-pyrimidin-2-ylamino)-4-
aminocyclohexane (30 mg, 0.12 mrnol) was added 4-methyl-benzoyI chloride (15.8 uL, 0.12
mmol) and DIEA (5 drops). The reaction was stirred overnight at room temperature under argon
gas. The solution was concentrated and the product purified using prep HPLC to give N-(cis-4-{[4-
(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-4-methylbenzamide trifluoroacetate
(29.1mg, 50.4 %) as a white solid.
ESI MS m/e 368 M + if; ]H NMR (400 MHz, DMSO-J5) 5 8.70 (s, 1 H), 7.68 (d, J= 8.0 Hz, 2 H),
7.24 (d, J = 8.0 Hz, 2 H), 6.72 (s, 1 H), 4.25 (s, 1 H), 3.23 (s, 6 H), 2.71 (s, 1 H), 2.34 (s, 3 H), 2.27
(s, 3 H), 1.7-1.88 (m, 8 H).
Example 2524
7V-(c/s-4-{[4-(Diinethylamino)-5-methylpyrimidiii-2-yllaniino}cyclohexyl)-3,4-
difluorobenzamide hydrochloride
Step A: Synthesis of iV-(c/s-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)-3,4-difluorobenzamide hydrochloride.
To a suspension of m-4-(4-dimethyIamino-5-methyl-pyrimidin-2-ylamino)-4-
aminocyclohaexane (70 mg, 0.28 mmol) in DC1-5 (5 mL) was added 3,4-difluorobenzoyl chloride
(50 mg, 0.28 mmol) and DIEA (45 \xL, 0.28 mmol). The reaction was stirred overnight and the
product was purified by column chromatography (silica gel, DC1-5/MeOH = 100:0 to 90:10). The
purified product was dissolved in DC1-5 (3 mL), and 2M-HC1 in ethyl ether (0.3 mL) was added.

502
After stirring 20 min, removal of the volatile solvent gave iV-(c/s-4-{[4-(dirnethylamino)-5-
methylpyrimidin-2-yI]amino}cyclohexyl)-3,4-difluorobenzamide hydrochloride (26 mg, 23 %) as a
white solid.
ESI MS m/e 390 M + If; ]H NMR (400 MHz, DMSOd6) 5 11.8 (brs, 1 H), 8.23 (brs, 1 H), 7.80
(m, 2 H), 7.63 (m, 1 H), 7.51 (s, 1 H), 7.40 (d, ./ = 8.8 Hz, 1 H), 3.74 (brs, 2 H), 3.14 (s, 6 H), 2.11
(s,3H), 1.73-1.58 (m, 8 H).
Example 2525
3-Chloro-Ar-(c/s-4-{[4-(dimethylamino)-5-methylpyrimidin-2-y1]amino}cyC1-5hexyl)benzaniide
hydrochloride
Step A: Synthesis of 3-chloro-7V-(c«-4-{[4-(dimethylainino)-5-niethylpyriinidin-2-
yl]amino}cyclohexyi)benzamide hydrochloride.
Using procedure of step A of example 2524, the title compound was obtained.
ESI MS m/e 388 M + H+; !H NMR (400 MHz, DMSO-d6) 5 11.7 (brs, 1 H), 8.22 (brs, 1 H), 7.72
(m, 2 H), 7.62 (d, J= 8.0 Hz, 1 H), 7.45 (s, 1 H), 7.42 (d, J= 8.0 Hz, 1 H), 7.32 (t, J= 7.6 Hz, 1 H),
3.70 (brs, 2 H), 3.10 (s, 6 H), 2.06 (s, 3 H), 1.68-1.54 (m, 8 H).
Example 2526
Ar-(c/$-4-{[4-(Dimethylamino)-6-methylpyriniidin-2-yl]amino}cyclohexyl)-3-methylbenzamide
trifluoro acetate
Step A: Synthesis of 2-chloro-4-dimethylamino-6-methylpyrimidine.
In 100 mL tetrahydrofuran was dissolved 2,4-dichloro-6-methylpyrimidine (10 g, 61.3
mmol) at 0° C. To the reaction mixture was added dimethylamine (2M in methanol, 67.4 mL,
134.8 mmol) dropwise. The reaction mixture was stirred at 10 °C for 2.5 hours. The solution was

503
concentrated and purified by flash chrornatography (silica gel, 20% ethyl acetate and 5% methanol
in hexanes) to give 2-chloro-4-dimethylamino-6-methylpyrimidine (4.18g, 40 %) as a pale yellow
solid.
ESI MS m/e 172 M + H+; 'H NMR (400 MHz, CDCI3) 6 6.25 (s, 1 H), 3.2 (s, 6 H), 2.64 (s, 3 H).
Step B: Synthesis of c/$-[4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino) cyclohexyl]-
carbamic acid tert-buty\ ester.
To a suspension of 2-chloro-4-dimethylamino-6-methylpyrimidine (15 mg, 0.0874 mmol)
in 2-propanol (1.7 mL) was added c/s-(4-amino-cyclohexyI)-carbamic acid tert- butyl ester (20.6
mg, 0.096 mmol) and DIEA (30.3 uL, 0.175 mmol). The reaction was performed in the Smith
synthesizer for 4.5 hours at 175 C. The solution was concentrated and purified by flash
chromatography (silica gel, 1% MeOH in CH?C12) to give cw-[4-(4-dimethylamino-6-methyl-
pyrimidin-2-ylamino) eyelohexyI]-carbarnic acid tert-b\xty\ ester (18.9 mg, 62 %) as a pale yellow
solid.
ESI MS m/e 350.4 M + >T; lH NMR (400 MHz, CDC13) 5 5.65 (s, 1 H), 4.75 (brs, 1 H), 4.0 (brs, 1
H), 3.60 (brs, 1 H), 3.05 (s, 6 H), 2.22 (s, 3 H), 1.78 (m, 6 H), 1.59 (m, 2 H), 1.44 (s, 9 H).
Step C: Synthesis of m-4-(4-dimethylamino-6-methyl-pyrimidin-2-yIamino)-4-
aminocyclohexane.
To a suspension of m-[4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino) cyclohexyl]-
carbamic acid /er/-butyl ester (617 mg, 1.77 mmol) in DC1-5 (3 mL) was added trifluoroacetic acid
(2mL). The reaction stirred at room temperature for 2 hours and concentrated. A few drops
NaHCO3 was added, followed by 1M NaOH until the solution was basic. The product was
extracted with H2O and CH2CI2 three times. The organic layers were combined, dried over MgSO4,
filtered and concentrated to give cJs-4-(4-dimethylamino-6-methyl-pyrimidin-2-yIamino)-4-
aminocyclohexane (318 mg, 72 %) as yellow oil.

504
ESIMSm/e250M + H+;]HNMR(400MHz, CDCI3) 6 5.52 (s, 1 H), 5.10 (brs, 1 H), 3.88 (brs, 1
H), 3.20 (brs, 2 H), 2.88 (s, 6 H), 2.75 (s, 1 H), 2.04 (s, 3 H), 1.70 (m, 2 H), 1.58 (m, 4 H), 1.38 (m,
2H).
Step D: Synthesis of 7V-(c/y-4-{[4-(dimethylamino)-6-methylpyriniidin-2-
yl]amino}cyclohexyl)-3-methylbenzamide trifluoroacetate.
Using the procedure of step D of example 2523, the title compound was obtained.
ESI MS m/e 368.4 M + H+; 'H NMR (400 MHz, DMSO-d6) 9,0 (s, 1 H), 7.6 (m, 2 H), 7.22 (s, 1 H),
6.72 (s, 1 H), 5.68 (s, 1 H), 4.2 (s, 1 H), 4.12 (s, 1 H), 3.18 (s, 3 H), 3.08 (s, 3 H), 2.35 (s, 3 H), 2.29
(s, 3 H), 1.85-1.62 (m, 8 H).
Example 2527
cw-4-{[4-(Dimethylamino)-6-methylpyrimidin-2-yl]amino}-A;-[3-(trifluoromethyl)benzyll-
cyclohexanecarboxamide
Step A: Synthesis of c/s-4-(4~dimethy!amino-6-methyl-pyrimidin-2-ylamino)
cyclohexanecarboxylic acid ethyl ester.
To a suspension of 2-chIoro-4-dimethylamino-6-methylpyrimidine (250 rag, 1.46 mmol) in
2-propanot (1.5 mL) was added c/s-4-amino-cyC1-5hexanecarboxylic acid ethyl ester hydrochloride
(330 mg, 1.59 mmol) and DIEA (0.60 mL, 3.44 mmol). The reaction was performed in the Smith
synthesizer for 1 hour at 155 °C. The solution was concentrated and purified by flash
chromatography (silica gel, 1% MeOH in CH2C12) to give c/s-4-(4-dimethylamino-6-methyl-
pyrimidin-2-ylamino) cyclohexanecarboxylic acid ethyl ester (378.9 mg, 84.7%) as a pale yellow
solid.
ESI MS m/e 307 M + tf; ]H NMR (400 MHz, DMSO-d6) 5 7.62 (brs, 1 H), 6.21 (s, 1 H), 4.04 (q,
J= 6.4 Hz, 2 H), 3.98 (brs, 1 H), 3.15 (s, 6 H), 2.20 (s, 3 H), 1.58-1.80 (m, 8 H), 1.20 (t,J= 6.0 Hz,
3H).

505
Step B: Synthesis of m-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)
cyclohexanecarboxylic acid.
To a suspension of ci5-4-(4-dimethylamino-6-methyI-pyrimidin-2-yIamino)
cyclohexanecarboxylic acid ethyl ester (597.6 mg, 1.95 mmol) in H2O (10 mL) and ethanol (0.3
mL) was added KOH (547 mg, 9.75 mmol). The reaction was stirred at 70 °C for 2.5 hours until
reaction was homogenous. The reaction was cooled in an ice bath and acidified with concentrated
HC1. The product was purified using flash chromatography (silica gel, 0-10% MeOH in CH2CI2) to
give c/s-4-(4-dimethylamino-6-rnethyl-pyrimidin-2-ylamino) cyclohexanecarboxylic acid (302 mg,
55%) as a white solid.
ESI MS m/e 279.2 M + *T; 'H NMR (400 MHz, CDC13) 5 8.50 (brs, 1 H), 5.79 (s, 1 H), 4.02 (brs,
1 H), 3.19 (brs, 6 H), 2.49 (brs, 1 H), 2.29 (s, 3 H), 2.05 (m, 2 H), 1.81 (m, 2 H), 1.64 (m, 4 H).
Step C: Synthesis of cw-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-A'-[3-
(trifluoromethyl)benzyl]-cyclohexanecarboxamide.
To a suspension of 3-trifluoromethyibenzylamine (14uL, 0.0987 mmol) and cis-4-(4-
dimethylamino-6-methyl-pyrimidin-2-y!amino) cyclohexanecarboxylic acid (25mg, 0.0898 mmol)
in DC1-5 (5 mL) was added HATU (37.5mg, 0.0987 mmol). The reaction stirred at room
temperature under argon for 30 seconds and triethylamine (5 drops) was added. The reaction
stirred under argon at room temperature for 16 hours. The reaction was quenched by diluting with
5 mL DC1-5, followed by washing twice with saturated NaHCO3 (5mL), twice with 1M HC1 (5mL)
and once with H2O (5mL). The product was purified by filtering through silica gel with 0-10%
MeOH in CH2CI? to give c/5-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-A^-[3-
(trifluoromethyl)benzyl]-cyclohexanecarboxamide (17.6mg, 45 %) as a white solid.
ESI MS m/e 436 M+H+; !H NMR (400 MHz, CDCI3) 5 8.01 (brs, 1 H), 7.59 (brs, 1 H), 7.53 (m, 2
H), 7.40 (m, 2 H), 5.76 (s, 1 H), 4.50 (d, J= 6.4 Hz, 2 H), 4.28 (brs, 1 H), 3.19 (s, 6 H), 2.39 (m, I
H), 2.30 (s, 3 H), 2.0 (m, 2 H), 1.87 (m, 4 H), 1.60 (m, 2 H).

506
Example 2528
c/5-4-{[4-(Dimethylamino)-5-methyIpyrimidin-2-yI]amino}-iV-[3-(propionylaiiiino)benzyi]-
cyclohexanecarboxamide
Step A: Synthesis of m-[4~(3-nitrobenzylcarbamoyl)-cyclohexyl]-carbamic acid
*er/-butyl ester.
c*s-4-(ter/-Butoxycarbonylamino)-cyclohexanecarboxylic acid (2.0 g, 8.2 mmol) and 3-
nitrobenzyl amine hydrochloride (1.54 g, 8.2 mmol) in DC1-5 (30 mL) was reacted in the presence
of HATU (3.5 g, 9.02 mmol) and Et3N (4 mL). The reaction was diluted with DC1-5, washed with
1N-HC1 and water, dried over MgSO4, and concentrated. From column chromatography (silica gel,
DC1-5/MeOH = 100:0 to 95 to 5), 2.7 g (90 %) of cw-[4-(3-nitrobenzylcarbamoyI)-cyC1-5hexyl]-
carbamic acid tert-buty\ ester was isolated.
ESI MS m/e 378 M + H+; lH NMR (400 MHz, CDC13) 8 8.11 (brs, 1 H), 8.09 (s, 1 H), 7.60 (d, J
= 8.0 Hz, 1 H), 7.48 (t, J = 7.6 Hz, 1 H), 6.17 (brs, 1 H), 4.72 (brs, 1 H), 4.53 (d, J = 6.0 Hz, 2 H),
3.74 (brs, 1 H), 2.27 (m, 1 H), 1.80-1.71 (m, 6 H), 1.65-1.59 (m, 2 H), 1.45 (s, 9 H).
Step B: Synthesis of ciy-4-amino-cyclohexanecarboxylic acid 3-nitro-benzamide
hydrochloride.
m-[4-(3-Nitrobenzy!carbamoyI)-cyclohexyI]-carbamic acid tert-buty\ ester (2.5 g, 6.6
mmol) was reacted in TFA/DC1-5 (1:2 = 23 mL) for 2 hr at room temperature. After removal of the
solvents, the residue was dissolved in DC1-5 (15 mL), and added 2M-HC1 in ethyl ether (2 eq.).
After stirring for 20 min at room temperature, the volatile solvent was removed to give cis-4-
amino-cyclohexanecarboxylic acid 3-nitro-benzamide hydrochloride (2.0 g, 95 %) as a yellowish
white solid.
ESI MS m/e 278 M + H+; !H NMR (400 MHz, DMSO-^) 5 8.53 (t, J = 6.0 Hz, 1 H), 8.07 (d, J =
7.6 Hz, 1 H), 8.06 (s, 1 H), 7.84 (brs, 2 H), 7.68 (d, J = 7.6 Hz, 1 H), 7.59 (t, J = 7.6 Hz, 1 H), 4.37
(d, J = 6.4 Hz, 2 H), 3.13 (m, 1 H), 2.40 (m, 1 H), 1.89 (m, 2 H), 1.68 (m, 4 H), 1.57 (m, 2 H).

507
Step C: Synthesis of cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexanecarboxylic acid 3-nitro-benzylamide.
2-Chloro-4-dimethylamino-5-methylpyrimidine (0.31 g, 1.8 mmol) and cw-4-amino-
cyclohexanecarboxylic acid 3-nitro-benzylamide hydrochloride (0.52 g, 1 eq.) in IPA (2.5 mL) and
DIEA (0.7 mL) was reacted in a Smith synthesizer. The reaction was diluted with DC1-5, washed
with 1N-HC1 and water, dried over MgSO4, and concentrated. The crude compound was purified
from column chromatography (silica gel, DC1-5/MeOH = 100:0 to 90:10) to give 0.23 g (31 %) of
cj5-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexanecarboxylic acid 3-nitro-
benzylamide.
ESIMSm/e413M + H"; *H NMR (400 MHz, CDC13) 5 8.11 (brs, 1 H), 8.03 (d, J= 8.0 Hz, 3 H),
7.95 (brs, 1 H), 7.62 (d, 7= 8.0 Hz, 1 H), 7.43 (t, J= 7.6 Hz, 1 H), 7.28 (s, 1H),4.51 (d, J= 5.6 Hz,
2 H), 4.33 (m, I H), 3.23 (s, 6 H), 2.39 (m, 1 H), 2.22 (s, 3 H), 2.02 (m, 2 H), 1.86 (ra, 4 H), 1.60
(m, 2 H).
Step D: Synthesis of c/s-4-(4-dimethylamino-5-methyI-pyrimidin-2-ylamino)-
cyclohexanecarboxylic acid 3-amino-benzylamide.
A solution of c/5-4-(4-dimethylamino-5-methyl-pyrimidin-2-yIamino)-cyclohexane
carboxylic acid 3-ammo-benzyIamide (0.21 g, 0.5 mmol) and 10 % Pd/C (50 mg) in EtOH (10 mL)
was stirred overnight under H2 atmosphere at room temperature. The reaction was filtered through
a pad of celite. After removal of the volatile solvent, the residue was purified from a short pad of
silica gel (DC1-5/MeOH = 100:0 to 80:20) to give 0.18 g (95 %) of c/s-4-(4-dimethylamino-5-
methyl-pyrimidin-2-ylamino)-cyclohexanecarboxylic acid 3-amino-benzylamide as the desired
product.
ESI MS m/e 383 M + H*;1 H NMR (400 MHz, CDC13) 5 7.29 (s, 1 H), 7.03 (t, J= 7.6 Hz, 1 H),
6.64 (m, 2 H), 6.51 (d, J= 8.0 Hz, 1 H), 4.33 (d, J= 5.6 Hz, 2 H), 4.25 (brs, 1 H), 3.19 (s, 6 H),
2.32 (m, 1 H), 2.19 (s, 3 H), 1.97-1.78 (m, 6 H), 1.62 (m, 2 H).

508
Step E: Synthesis of cw-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-iV-[3-
(propionylamino)benzyl]cyclohexanecarbo\amide.
c«-4-(4-Dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyC1-5hexanecarboxyIic acid 3-
amino-benzylamide (30 mg, 0.075 mmol) and propionyl chloride (7 mg, 0.075 mmol) was reacted
in the presence of catalytic Et3N (7 drops). The product was purified from column chromatography
(silica gel, DC1-5/MeOH = 100:0 to 90:10) to give a'j-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yl]amino}-Ar-[3-(propionylamino)benzyl]cyclohexanecarboxamide (11 mg, 32 %).
ESI MS m/e 439 M + H+; *H NMR (400 MHz, CDC13) 5 8.63 (brs, 1 H), 7.92 (brs, 1 H), 7.35 (s, 1
H), 7.28 (s, 1 H), 7.21 (t, J= 7.6 Hz, 1 H), 6.92 (d, J= 7.6 Hz, 1 H), 6.46 (brs, 1 H), 4.42 (d, J= 6.0
Hz, 2 H), 4.23 (m, 1 H), 3-22 (s, 6 H), 2.47 (d, J = 7.6 Hz, 2 H), 2.33 (m, 1 H), 2.22 (s, 3 H), 1.95-
1.90 (m, 6 H), 1.63 (m, 2 H), 1.22 (t, J= 7.6 Hz, 3 H).
Example 2529
c/s-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]aniino}-A'-[3-(isobutyrylamino)benzyl]-
cyclohexanecarboxamide
Step A: Synthesis of c/y-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-Ar-[3-
(isobutyrylamino)benzyljcyclohexanecarboxamide.
Using the procedure of step E of example 2528, the title compound was obtained.
ESI MS m/e 453 M + H"; lH NMR (400 MHz, CDC13) 5 8.80 (brs, 1 H), 8.10 (brs, 1 H), 7.93 (brs,
1H), 7.39 (s, 1H), 7.23 (s, 1 H), 7.18 (t,J= 7.6 Hz, 1 H), 6.91 (d,J= 7.6 Hz, 1 H), 6.69 (brs, 1 H),
4.40 (d, J= 5.6 Hz, 2 H), 4.22 (m, 1 H), 3.23 (s, 6 H), 2.74 (m, 1 H), 2.33 (m, 1 H), 2.20 (s, 3 H),
1.96-1.87 (m, 6 H), 1.60 (m, 2 H), 1.22 (d, J= 6.4 Hz, 6 H).

509
Example 2530
cw-4-{[4-(Diinethylamino)-5-methylpyrimidin-2-yl]aniino}-A'-{3-[(3-methyIbutanoyl)amino]-
benzyl}cyclohexanecarboxamide.
Step A: Synthesis of c/s-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-A'-{3-[(3-
methylbutanoyl)amino]benzyl}cyclohexanecarboxamide.
Using the procedure of step E of example 2528, the title compound was obtained.
ESI MS m/e 467 M + H+; 'H NMR (400 MHz, CDC!3) 6 8.62 (brs, 1 H), 8.04 (brs, 1 H), 7.91 (d, J
= 7.2 Hz, 1 H), 7.35 (s, 1 H), 7.26 (s, 1 H), 7.20 (t, J= 7.6 Hz, I H), 6.93 (d, J= 7.6 Hz, 1 H), 6.59
(brs, 1 H), 4.42 (d, 7=5.2 Hz, 2 H), 4.22 (m, 1 H), 3.23 (s, 6 H), 2.33 (m, 1 H),2.31 (d, .7=7.2 Hz,
2 H), 2.23 (m, 1 H), 2,21 (s, 3 H), 1.96-1.87 (m, 6 H), 1.62 (m, 2 H), 1.00 (d, J= 6.0 Hz, 6 H).
Example 2531
m-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}-Ar-{3-[(2,2-dimethyI-
propanoy!)amino]benzyl}cyclohexanecarboxamide
Step A: Synthesis of c«-4-{[4-(dimethylamino)-5-methyIpyrimidin~2-yl]amino}-iV-{3-[(2,2-
dimethylpropanoyl)amino]benzyl}cyclohexanecarboxamide.
Using the procedure of step E of example 2528, the title compound was obtained.
ESI MS m/e 467 M + FT; 1H NMR (400 MHz, CDC13) 8 7.84 (brs, 1 H), 7.78 (d, J= 7.6 Hz, 1 H),
7.40 (s, 1 H), 7.25 (s, 1 H), 7.22 (t, 7 = 7.6 Hz, 1 H), 7.00 (d, 7 = 7.6 Hz, 1 H), 6.85 (brs, 1 H), 4.41
(d, 7 = 5.6 Hz, 2 H), 4.23 (m, 1 H), 3.23 (s, 6 H), 2.34 (m, 1 H), 2.22 (s, 3 H), 1.99-1.84 (m, 6 H),
1.60 (m, 2 H), 1.33 (s, 9 H).

510
Example 2532
cw-Ar-{3-[(CyC1-5butylcarbonyl)amino]benzyl}-4-{[4-(dimethylamino)-5-niethylpyriniidin-2-
yljaminojcyclohexanecarboxamide
Step A: Synthesis of c«-yV-{3-[(cyclobutylcarbonyl)amino]benzyl}-4-{[4-(dimethylamino)-5-
methyIpyrimidin-2-yl]amino}cyC1-5hexanecarboxamide.
Using the procedure of step E of example 2528, the title compound was obtained.
ESI MS m/e 465 M + H"; 'H NMR (400 MHz, CDCI3) 5 8.50 (brs, 1 H), 8.23 (brs, 1 H), 7.93 (d, J
-6.4 Hz, 1 H), 7.33 (s, 1 H), 7.24 (s, 1 H), 7.20 (t, J= 8.0 Hz, 1 H), 6.92 {&yJ= 8.0 Hz, 1 H), 6.76
(brs, 1 H),4.41 (d, J= 5.6 Hz, 2 H), 4.23 (m, 1 H), 3.33 (m, 1 H), 3.24 (s, 6 H), 2.35 (m, 4 H), 2.21
(s, 3 H), 2.18 (m, 1 H), 2.00-1.87 (m, 8 H), 1.60 (m, 2 H).
Example 2533
m-Ar-{3-[(CyC1-5pentylcarbonyl)amino]benzyl}-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide
Step A: Synthesis of C1-5-Ar-{3-[(cyclopentylcarbonyI)amino]benzyl}-4-{[4-(dimethyIamino)-5-
methylpyrimidin-2-yl]amino}cyC1-5hexanecarboxamide.
Using the procedure of step E of example 2528, the title compound was obtained.
ESI MS m/e 479 M + H+; *H NMR (400 MHz, CDC13) 5 8.47 (brs, 1 H), 8.10 (brs, 1 H), 7.91 (d, J
= 6.4 Hz, 1H), 7.35 (s, 1 H), 7.26 (s, 1 H), 7.20 (t, J= 8.0 Hz, 1 H), 6.93 (d, 7= 7.6 Hz, 1 H), 6.61
(brs, 1 H), 4.42 (d, J= 5.6 Hz, 2 H), 4.22 (m, 1 H), 3.22 (s, 6 H), 2.85 (m, 1 H), 2.33 (m, 1 H), 2.21
(s, 3 H), 2.00-1.88 (m, 10 H), 1.75 (m, 2 H), 1.60 (m, 4 H).

511
Example 2534
c/s-A^iS-ItCyclohexylcarbony^aminolbenzylJ-^lf^dimethylamino^S-methylpyrimidin-l-
yl]amino}cyclohexanecarboxamide.
StepA: Synthesis of cw-7V-{3-[(cyclohexylcarbonyl)amino]benzyI}-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyC1-5hexanecarboxamide.
Using the procedure of step E of example 2528, the title compound was obtained.
ESI MS m/e 493 M + HV H NMR (400 MHz, CDC13) 5 8.30 (brs, 1 H), 8.01 (brs, 1 H), 7.86 (d, J
= 7.6 Hz, I H), 7.36 (s, 1 H), 7.26 (s, 1 H), 7.20 (t, J= 8.0 Hz, 1 H), 6.94 (d, J= 7.6 Hz, 1 H), 6.65
(brs, 1 H), 4.41 (d,J= 5.2 Hz, 2 H), 4.22 (m, I H), 3.22 (s, 6 H), 2.35 (m, 2 H), 2.21 (s, 3 H), 196-
1.28 (m, 18 H).
Example 2535
ci5-Ar-{3-[(CyclopropylcarbonyI)aminoJbenzyl}-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide
Step A: Synthesis of c/s-Ar-{3-[(cyclopropylcarbonyl)amino]benzyI}-4-{[4-(dimethylamino)-5-
methyIpyrimidin-2-yI]amino}cyC1-5hexanecarboxamide.
Using the procedure of step E of example 2528, the title compound was obtained.
ESI MS m/e 451 M + H+; 'H NMR (400 MHz, CDC13) 5 9.10 (brs, 1 H), 7.93 (m, 1 H), 7.36 (s, 1
H),7.25(s, 1 H), 7.19(t,J=8.0Hz, 1 H), 6.90 (d, J= 7.2 Hz, 1 H), 6.50 (brs, 1 H), 4.43 (d, J= 6.0
Hz, 2 H), 4.23 (m, 1 H), 3.23 (s, 6 H), 2.33 (m, 1 H), 2.21 (s, 3 H), 1.96-1.88 (m, 7 H), 1.63 (m, 2
H), 1.03 (m, 2 H), 0.79 (m, 2 H).
Example 2536

512
Ar-[(c/5-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yI]aiiiino}cyclohexyl)methylJ-3-[(3-
methylbutanoyl)amino]benzamide.
Step A: Synthesis of {c/y-4-[(3-nitro-benzoylamino)-methyl]-cyC1-5hexyl}-carbamic
acid tert-buty\ ester.
A mixture of c/s-(4-aminomethyl-cyclohexyl)-carbamic acid tert-buty] ester (1.55 g, 6.8
mmol) and 3-nitrobenzoyl chloride (1.25 g, 6.8 mmol) was stirred overnight at room temperature,
diluted with DC1-5, washed with 1N-HC1 and water, and concentrated. The crude product was
preliminary purified by a short pad of silica gel with DC1-5/MeOH (100:0 to 90:10) to give 1.5 g
(75 %) of {c/5-4-[(3-nitro-benzoylamino)-methyl]-cyclohexyl}-carbamic acid tert-buty\ ester.
ESI MS m/e 378 M + H";1 H NMR (400 MHz, CDC13) S 8.54 (t, J = 2.0 Hz, 1 H), 8.33 (d, / = 8.0
Hz, 1 H), 8.14 (d,.7=8.0 Hz, 1 H), 7.63 (t, J-7.6 Hz, 1 H), 6.31 (brs, 1 H), 4.62 (brs, 1 H), 3.73
(brs, 1 H), 3.41 (t, J = 6.4 Hz, 2 H), 1.72-1.57 (m, 7 H), 1.44 (s, 9 H), 1.32 (m, 2 H).
Step B: Synthesis of ci5-A^4-amino-cyclohexylmethyI)-3-nitro-benzamide hydrochloride.
{c/5-4-[(3-Nitro-benzoylamino)-methyl]-cyclohexyl}-carbamic acid tert-huty\ ester (1.4 g,
3.7 mmol) in DC1-5/TFA (1:1 = 13 mL) was stirred for 2 h at room temperature. After removal of
the volatile solvent, the residue was dissolved in DC1-5 (10 mL), and 2M-HC1 in ether (4 mL) was
added. After stirring for 20 min at room temperature, removal of the volatile solvent gave 1.2 g
(82 %) of c/5-jV-(4-amino-cyC1-5hexylmethyl)-3-nitro-benzamide hydrochloride as the desired
product.
ESI MS m/e 278 M + H+; lH NMR (400 MHz, DMSC1-5J) 5 8.91 (t, J = 5.6 Hz, 1 H), 8.65 (m, 1
H), 8.36 (d, J = 2.0 Hz, 1 H), 8.29 (d, J = 8.0 Hz, 1 H), 7.97 (brs, 2 H), 7.74 (t, J = 8.0 Hz, 1 H),
3.25 (t, J = 6.8 Hz, 2 H), 3.13 (brs, 1 H), 1.77 (m, 1 H), 1.65-1.61 (m, 4 H), 1.51 (m, 4 H).
Step C: Synthesis of c/5-Air-[4-(4-diinethylamino-5-methyl-pyriinidin-2-ylamino)-
cyclohexylmethyl]-3-nitro-benzamide.

513
A solution of 2-chioro-4-dimethylamino-5-methylpyrimidine (0.25 g, 1.46 mmol) and cis-
N-(4-amino-cyclohexylmethyl)-3-nitro-benzamide hydrochloride (0.46 g) in IPA (2 mL) and DIEA
(0.46 mL) was reacted for 1 hr 10 min. at 155 °C in a Smith synthesizer. The reaction was diluted
with DC1-5, washed with 1N-HC1 and water, dried over MgSO4, and concentrated. The crude
compound was purified from column chromatography (silica gel, DC1-5/MeOH = 100:0 to 90:10)
to give 0.23 g (38 %) of c«-Ar-[4-(4-dimethyJamino-5-methyl-pyrimidin-2-yIamino)-
cyclohexylmethyI]-3-nitro-benzamide.
ESI MS m/e 413.2 M + H+; !H NMR (400 MHz, CDCI3) 6 8.73 (t, J= 2.0 Hz, 1 H), 8.34 (d, J= 7.6
Hz, 1 H), 8.28 (d, J= 8.0 Hz, , 1 H), 8.20 (brs, 1 H), 7.60 (t, J= 7.6 Hz, 1 H), 7.35 (brs, 1 H), 7.25
(s, 1 H), 4.18 (m, 1 H), 3.48 (t, J= 4.8 Hz, 2 H), 3.24 (s, 6 H), 2.21 (s, 3 H), 1.89-1.57 (m, 9 H).
Step D: Synthesis of Ar-[(ci.s-4-{[4-(dimethylaniino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyl)methyl]-3-I(3-methylbutanoyl)amino]benzamide.
A solution of c«-jV-[4-(4-dimethylamino-5-methyl-pyrimidin-2-yIamino)-
cyclohexylmethyl]-3-nitro-benzamide (0.22 g, 0.53 mmol) and 10 % Pd/C (30 mg) in EtOH (15
mL) was stirred overnight under H2 atmosphere at room temperature. The reaction was filtered
through a pad of celite. After removal of the volatile solvent, the residue was purified from a short
pad of silica gel (DC1-5/MeOH = 100:0 to 80:20) to give 0.19 g (95 %) as yellowish oil. 17 mg
(0.04 mmol) of this oil was reacted with isovaleryl chlorides (5 mg, 0.04 mmol) using the
procedure of step E of example 2528 to give Af-[(c/5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)methyl]-3-[(3-methylbutanoyl)amino]benzamide (9 mg, 47 %).
ESI MS m/e 467.6 M + H+; 'H NMR (400 MHz, CDC13) 5 9.11 (brs, 1 H), 8.22 (d,J= 7.2 Hz, 1 H),
8.04 (s, 1H), 7.55 (d, J =7.6 Hz, 1 H), 7.34 (t, J= 7.6 Hz, 1 H), 7.30 (s, 1 H), 6.42 (m, 1 H), 4.14
(m, 1 H), 3.43 (t, J = 4.8 Hz, 2 H), 3.19 (s, 6 H), 2.33 (d, J= 6.8 Hz, 2 H), 2.25 (m, 1 H), 2.20 (s, 3
H), 1.94 (m, 2 H), 1.72-1.59 (m, 7 H), 1.02 (d, J = 6.4 Hz, 6 H).

514
Example 2537
7V-[(c/5-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)methyl]-3-
(propionylamino)benzamide
Step A: Synthesis of 7V-[(ctf-4-{[4-(dimethyIamino)~5-methylpyrimidin-2-yl]ainino}-
cyclohexyl)methyl]-3-(propionylamino)benzamide.
Using the procedure of step D of example 2536, the title compound was obtained.
ESI MS m/e 439 M + H+; lH NMR (400 MHz, CDC13) 5 9.10 (brs, 1 H), 8.23 (d, J= 7.2 Hz, 1 H),
8.02 (s, 1 H), 7.55 (d,J= 8.0 Hz, 1 H), 7.35 (t, J= 7.6 Hz, 1 H), 7.29 (s, 1 H), 6.36 (m, 1 H), 4.16
(brs, 1 H), 3.47 (m, 2 H), 3.21 (s, 6 H), 2.50 (q, J = 7.6 Hz, 2 H), 2.21 (s, 3 H), 1.95 (m, 2 H), 1.72-
1.61 (m, 7 H), 1.25 (t, J= 7.2 Hz, 3 H).
Example 2538
Ar-[(C1-5-4-{[4-(Dimethylamino)-S-methylpyrimidin-2-yl]ainino}cyclohexyl)methyl]-3-
(isobutyrylamino)benzamide
Step A: Synthesis of Ar-[(C1-5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)methyl]-3-(isobutyrylamino)benzamide
Using the procedure of step D of example 2536, the title compound was obtained.
ESI MS m/e 453 M + H"; ]H NMR (400 MHz, CDCI3) 5 9.09 (brs, 1 H), 8.23 (d, J= 6.8 Hz, 1 H),
8.07 (s, 1 H), 7.55 (d, J= 7.6 Hz, 1 H), 7.34 (t, J= 7.6 Hz, 1 H), 7.29 (s, 1 H), 6.38 (m, 1 H), 4.16
(brs, 1 H), 3.45 (m, 2 H), 3.21 (s, 6 H), 2.73 (m, 1 H), 2.20 (s, 3 H), 1.95 (m, 2 H), 1.72-1.61 (m, 7
H), 1.26 (d, .7=6.8 Hz, 6 H).

515
Example 2539
3-[(CyC1-5propykarbonyl)amino]-7V-[(c/5-4-{[4-(diniethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)methyl]benzamide
Step A: Synthesis of 3-[(cyclopropylcarbonyl)amino]-jV-[(c«-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)methy)]benzamide
Using the procedure of step D of example 2536, the title compound was obtained.
ESI MS m/e 451 M + ¥t; lH NMR (400 MHz, CDCI3) 5 9.60 (brs, 1 H), 8.22 (d, J= 6.8 Hz, 1 H),
8.03 (s, 1 H), 7.56 (brs, 1 H), 7.55 (d, J= 7.6 Hz, 1 H), 7.32 (t, 7= 7.6 Hz, 1 H), 7.28 (s, 1 H),6.41
(m, 1 H), 4.15 (brs, 1 H), 3.45 (m, 2 H), 3.21 (s, 6 H), 2.20 (s, 3 H), 1.95 (m, 2 H), 1.89 (m, 1 H),
1.72-1.61 (m, 7 H), 1.05 (m, 2 H), 0.82 (m, 2 H).
Example 2540
3-((Cyclobutylcarbonyl)amino]-Ar-[(ci$-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)methyljbenzamide
Step A: Synthesis of 3-[(cyclobutylcarbonyI)amino]-7V-[(m-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl}amino}cyclohexyl)methyl]benzamide.
Using the procedure of step D of example 2536, the title compound was obtained.
ESIMSm/e465M + H+;lHNMR(400MHz,CDCI3)5 8.90(brs, I H), 8.21 (d, 7=6.8 Hz, 1 H),
8.04 (s, 1 H), 7.54 (d, 7=8.0 Hz, I H), 7.34 (t, J= 7.6 Hz, 1 H), 7.31 (s, 1 H), 6.41 (m, 1 H), 4.14
(brs, 1 H), 3.43 (X,J = 5.2 Hz, 2 H), 3.34 (m, 1 H), 3.19 (s, 6 H), 2.41 (m, 2 H), 2.23 (m, 1 H), 2.20
(s, 3 H), 2.02-1.88 (m, 4 H), 1.72-1.55 (m, 8 H).

516
Example 2541
3-[(Cyclopentylcarbonyl)amino]-Ar-[(c«-4-{[4-(dimethylaiiiino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)methyl]benzamide.
Step A: Synthesis of 3-[(cyclopentylcarbonyI)amino]-7V-[(C1-5-4-{[4-(dimethylamino)-5-
methyIpyrimidin-2-yl]amino}cyclohexyl)methyllbenzamide.
Using the procedure of step D of example 2536, the title compound was obtained.
ESI MS m/e 479 M + H+; lH NMR (400 MHz, CDC13) 5 9.14 (brs, 1 H), 8.22 (d, J= 7.2 Hz, 1 H),
8.07 (s, 1 H), 7.54 (d, J= 8.0 Hz, 1 H), 7.33 (t, J= 8.0 Hz, 1 H), 7.29 (s, I H), 6.43 (m, I H), 4.14
(brs, 1 H), 3.44 (t, J = 5.2 Hz, 2 H), 3.19 (s, 6 H), 2.91 (m,l H), 2.20 (s, 3 H), 1.98-1.59 (m, 17 H).
Example 2542
3-[(Cyclohexylcarbonyl)amino]-A'-[(cw-4-{[4-(dimethyIamino)-5-methylpyrimidiii-2-
yl]amino}cyclohexyl)methyl]benzamide
Step A: Synthesis of 3-[(cyclohexylcarbonyl)amino]-Af-[(m~4-{[4-(dimethylamino)-5~
methylpyrimidin-2-yl]amino}cyclohexyl)methyl]benzamide.
Using the procedure of step D of example 2536, the title compound was obtained.
ESI MS m/e 479 M + FT; (H NMR (400 MHz, CDC13) 5 8.94 (brs, 1 H), 8.17 (d, J= 7.2 Hz, 1 H),
8.05 (s, 1 H), 7.54 (d,J-8.0 Hz, 1 H), 7.33 (t, J= 8.0 Hz, 1 H), 7.30 (s, 1 H), 6.44 (m, 1 H), 4.13
(brs, 1 H), 3.42 (t,J = 5.2 Hz, 2 H),3.19 (s, 6 H), 2.42 (m,l H), 2.20 (s, 3 H), 1.98-1.52 (m, 15 H),
1.29 (m, 4 H).
Examples 2543-2553
Compounds 2543 to 2553 were prepared in a similar manner as described in Example 2497
using the appropriate acid chloride and amine intermediate from Step D.

517
Examples 2554-2557
Compounds 2554 to 2557 were prepared in a similar manner as described in Example 2502
using the appropriate carboxylic acid and amine intermediate from Example 2497 Step D.
Examples 2558-2561
Compounds 2558 to 2561 were prepared in a similar manner as described in Example 2515
using the appropriate isocyanate and amine intermediate from Example 2497 Step D.
Examples 2562 and 2563
Compounds 2562 and 2563 were prepared in a similar manner as described in Example
2523 using the appropriate acid chloride and amine intermediate from Step C.
Examples 2564-2570
Compounds 2564 to 2570 were prepared in a similar manner as described in Example 2526
using the appropriate acid chloride and amine intermediate from Step C.
Examples 2571-2587
Compounds 2571 to 2587 were prepared in a similar manner as described in Example 2527
using the appropriate benzyl amine and carboxylic acid intermediate from Step B.

518

Ex. No. compound name MS class
2543 3-methyl-N-{cis-4-[(4-methy!quinolin-2-
yl)aminolcyclohexyl}benzamide 374.2 (M + H) 1
2544 4-methyl-N-{cis-4-[(4-methyiquinoIin-2-
vl)aminolcyclohexyl}benzamide 374.2 (M + H) 1
2545 4-fluoro-N-{cis-4-[(4-methylquinolin-2-
yl)aminolcyclohexyl}benzamide 378.2 (M + H) 1
2546 N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}-3-
f tr i fl uoromethyl )be n zam i de 428 (M + H)
2547 3-chloro-N-{cis-4-[{4-methyIquinolin-2-
yl)aminolcyclohexyl}benzamide 394.2 (M + H) 1
2548 N-{cis-4-[(4-methyIquinolin-2-yJ)amino]cyclohexyl}-3,5-
bisftrifluoromethyl)benzamide 496.2 (M + H) 1
2549 3-methoxy-N-{cis-4-[(4-methylquinolin-2-
yl)aminolcvclohexyl}benzamide 390.4 (M + H) 1
2550 3-cyano-N-{cis-4-[(4-methyIquinoIin-2-
yl)amino]cyclohexyl}benzamide 385.2 (M + H) 1
2551 2-(4-chIorophenoxy)-N-{cis-4-[(4-methyIquinolin-2-
yl)amino1cvclohexyl} acetamide 424.2 (M + H) 1
2552 3,4,5-trimethoxy-N-{cis-4-[(4-methylquinolin-2-
yl)amino]cyclohexy]}benzamide 450.4 (M + H) 1
2553 3,5-dimethoxy-N-{cis-4-[(4-methyIquinoIin-2-
yl)aminolcyclohexyl}benzamide 420.2 (M + H) 1
2554 2-(3-methoxyphenoxy)"N-{cis-4-[(4-methylquinolin-2-
yl)amino]cyclohexyl}acetamide 420.2 (M + H) 1
2555 (2R)-2-(3-chIorophenyl)-2-hydroxy-N-{cis-4'[(4-methylquinolin-
2-yI)aminolcyclohexyl}acetamide 424.2 (M + H) 1
2556 2-(3-methylphenoxy)-N-{cis-4-[(4-methylquinolin-2-
yl)aminolcyclohexyl)acetamide 404.2 (M + H) 1
2557 5-bromo-N-{cis-4-[(4-methylquinoIin-2-yl)amino]cyclohexyl}-2-
furamide 428 (M + H) 1
2558 N-[4-(benzyloxy)phenyl]-N'-{cis-4-[(4-methylquinolin-2-
vl)aminolcyclohexyl}urea 481.2 (M + H) 2
2559 N-{cis-4-[(4-methylquinolin-2-yl)amino]cyC1-5hexyl}-N'-(4-
phenoxyphenv! )urea 467.4 (M + H) 1
2560 N-{cis-4-[(4-methyIquinoIin-2-yl)amino]cyclohexyl}-N'-(3-
phenoxyphenyl)urea 467.4 (M + H) 2
2561 N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}-N'-(2-
phenoxyphenyl)urea 467.4 (M + H) 1
2562 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino)cyclohexyl)-3-methyIbenzamide 368.2 (M + H) 1
2563 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyl)-3-methoxybenzamide 384.2 (M + H) 1
2564 N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)-3-methoxybenzamide 384.2 (M + H) 1
2565 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)-4-methylbenzamide 368.2 (M + H) 1
2566 4-chloro-N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2"
yl]amino}cyclohexyl)benzamide 388.2 (M + H) 1

519

Ex. No. compound name MS class
2567 3-chloro-N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-
yllamino}cyclohexyl)benzamide 388.4 (M + H) 1
2568 N-(cis-4-{[4-(dimethyiamino)-6-methylpyrimidin-2-
vl]amino}cyclohexyl)-3,4-difluorobenzamide 390.2 (M + H) 1
2569 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}cyC1-5hexyl)-4-(trifluoromethoxy)benzamide 438.2 (M + H) 3
2570 N-(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-
vllamino}cyclohexyl)-4-fluorobenzamide 372.2 (M + H) 1
2571 cis-4- {[4-(dimethy lamino)-6-methy lpyrimidin-2-yl]amino} -N-(3-
iodobenzyl)cyclohexanecarboxamide 494.2 (M + H) 1
2572 cis-N-(2,4-dichlorobenzyl)-4-{[4-(dimethylamino)-6-
methyIpyrimidin-2-yllamino}cyclohexanecarboxamide 436.2 (M + H) 1
2573 cis-N-(2,5-dichlorobenzyl)-4-{[4-(dimethylamino)-6-
methyIpyrimidin-2-yl1amino}cyclohexanecarboxamide 436.2 (M + H) 1
2574 cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}-N-(4-
methylbenzyl)cvclohexanecarboxamide 382.2 (M + H) 1
2575 cis-N-(3,5-dichlorobenzyl)-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yllamino|cyC1-5hexanecarboxamide 436.2 (M + H) 1
2576 cis-N-(3,5-dimethoxybenzyI)-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yllamino}cyclohexanecarboxamide 428.2 (M + H) 1
2577 cis-N-(3-chlorobenzyl)-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yIlammo}cvC1-5hexanecarboxamide 402.2 (M + H) 1
2578 cis-N-[3,5-bis(trifIuoromethyl)benzyl]-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yllamino}cyclohexanecarboxamide 504.2 (M + H) 1
2579 cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-(3-
methoxvbenzyl)cyclohexanecarboxamide 398.2 (M + H) 1
2580 cis-N-(4-ch!orobenzyI)-4- {[4-(dimethyIamino)-6-
methylpyrimidin-2-yIlamino}cyclohexanecarboxamide 402.2 (M + H) 1
2581 cis-N-(3,4-dichlorobenzyI)-4-{[4-(dimethylamino)-6-
methylpvrimidin-2-yllamino}cyclohexanecarboxamide 436.2 (M + H) 1
2582 cis-N-(2,4-difluorobenzyl)-4- {[4-(dimethylaraino)-6-
methylpyrimidin-2-yllamino}cyclohexanecarboxamide 404.2 (M + H) 1
2583 cis-N-(2,5-difIuorobenzyI)-4-{[4-(dimethylamino)-6-
methylpyriraidin-2-yllamino}cyc]ohexanecarboxamide 404.2 (M + H) 1
2584 cis-N-(2,3-difluorobenzyl)-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yIlamino}cyclohexanecarboxamide 404.2 (M + H) 1
2585 cis-N-(4-bromo-2-fluorobenzyl)-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yllamino}cyclohexanecarboxamide 464.2 (M + H) 1
2586 cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}-N-(3-
methylbenzyl)cyclohexanecarboxamide 382.4 (M + H) 1
2587 cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-[2-
f tri fl uoromethoxy)ben zy 11 eye 1 ohexanecarboxam i de 452.2 (M + H) 1

520
Example 2588
Ar-(cw-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
bis(trifluoromethyl)benzamidehydrochloride
Step A: Synthesis of N-(c/5-4-amino-cyclohexyl)-3,5-bistrifluoromethyl-benzamide
trifluoroacetate.
To a solution of c/s-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester (2.18 g, 10 mmol)
in anhydrous benzene (25 mL) was slowly added 3,5-bistrifluoromethyl benzoyl chloride (2.8 g, 1
eq.) and followed by Et3N (~3mL) at room temperature under N? atmosphere: formation of solid
salts makes stirring difficult. The reaction was stirred vigorously for an additional 2 h at room
temperature, washed with sat.-NaHCO3 (3x) and water (lx), dried with MgSO4, and concentrated
to give [c«-4-[(3,5-bistrifluoromethyI-benzoylamino)-cyclohexyl]-carbamic acid tert-butyi ester
(4.5 g, 99 %), which was used for the next reaction without further purification. ESI MS m/e 455
(M + H)+; 'H NMR (400 MHz, CDC13) 5 8.16 (s, 2 H), 7.98 (s, 1 H), 6.12 (bs, 1 H), 4.58 (bs, 1 H),
4.1 l(m, lH),3.69(bs, 1 H), 1.95-1.65 (m, 8 H), 1.44 (s, 9 H).
[cw-4-[(3,5-Bistrifluoromethyi-benzoylamino)-cyclohexyl]-carbamic acid tert-butyl ester
(4.5 g, 10 mmol) was dissolved in DC1-5 (20 mL), and TFA (10 mL) was added to the reaction.
After 1.5 h stirring at room temperature, removal of the volatile solvent gave the crude N-(cw-4-
amino-cyclohexyl)-3,5-bistrifluoromethyl-benzarnide trifluoroacetate as a sticky oil. With addition
of water (-50 mL) to the crude product, shaking for 5 to 10 min provided formation of precipitates.
The precipitates were filtered, washed with water, and dried. 3.98 (82 %) of N-(cw-4-amino-
cyclohexyl)-3,5-bistrifluoromethyl-benzamide trifluoroacetate was isolated as a white powder. ESI
MS m/e 355 (M + H)+; 'HNMR (400 MHz, DMSC1-5s) 5 8.62 (bd, 1 H, J - 4.8 Hz), 8.47 (s, 2 H),
8.29 (s, 1 H), 7.84 (bs, 3 H), 3.91 (bs, 1 H), 3.16 (bs, 1 H), 1.94 (m, 2 H), 1.75-1,66 (m, 6 H).
Step B: Synthesis of yV-(cw-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]araino}-
cyclohexyl)-3,5-bis(trifluoromethyl)benzamide hydrochloride.
A sealed tube containing 2-chloro-4-dimethylamino-5-rnethylpyrimidine (0.25 g, 1.45

521
mmol), N-(cw-4-amino-cyclohexyl)-3,5-bistrifluoromethyI-benzamide trifluoroacetate (0.68 g, 1
eq.), DIEA (0.5 mL, 2 eq.), and tert-BuOH (2.5 mL) was reacted for 2 h at 180 °C in a Smith
microwave synthesizer: over 95 % conversion was observed by LC-MS. The reaction was diluted
with DC1-5, washed with diluted-HCl and water, dried, and concentrated. 0.35 g (48 %) of N-[c/5-
4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyC1-5hexyl]-3,5-bistrifluoromethyl-
benzamide was isolated by column chromatography (silica gel; DC1-5:MeOH = 100:0 to 95:5).
To a solution of this neutral compound in DC1-5 (10 mL) was added 4M-HC1 in dioxane
(0.4 mL, 2 eq.). After 30 min stirring at room temperature, removal of the volatile solvent provided
Ar-(c«-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino} cydohexyI)-3,5-
bis(trifluoromethyl)benzamide hydrochloride as a white powder. ESI MS m/e 490 (M + H)+; !H
NMR (400 MHz, DMSO-^6) 5 12.1 (bs, 1 H), 8.78 (bd, 1H,J- 5.6 Hz), 8.48 (s, 2 H), 8.28 (s, 1 H),
8.05 (bd, 1 H, J = 6.4 Hz), 7.62 (s, 1 H), 3.91 (bs, 2 H), 3.26 (s, 6 H), 2.23 (s, 3 H), 1.87 (m, 2 H),
1.73 (bs, 6 H).
Example 2589
yV-[(d5-4-{[4-(Dimethylamino)-5-methylpyriniidin-2-yl]amino}cyclohexyl)methyl]-3,5-
bis(trifluoromethyl)benzamide hydrochloride
Step A: Synthesis of N-(c«-4-amino-cyclohexylmethyl)-3,5-bistrifluoromethyl-benzaniide
trifluoroacetate.
To a solution of m-(4-aminomethyl-cyclohexyl)-carbamic acid tert-buty\ ester (1.1 g, 4.8
mmol) in dry benzene (15 mL) was added 3,5-bistrifluoromethyI benzoyl chloride (1.33 g, 1 eq.)
and followed by Et3N (2 mL) at room temperature under N2. The reaction was stirred for an
additional 2 h at room temperature, washed with sat-NaHCO3 (3x) and water (lx), dried with
MgSO4, and concentrated. The crude {ci5-4-[(3,5-bistrifluoromethyl-benzoylamino)-methyl]-
cyclohexyl}-carbamic acid tert-butyl ester was used for the next reaction without further
purification.

522
To a solution of {c/5-4-[(3,5-bistrifluoromethyl-benzoylamino)-methyI]-cyclohexyI}-
carbamic acid tert-butyl ester (2.1 g, 4.5 mmol) in DC1-5 (10 mL) was added TFA (5 mL) at room
temperature. After 1.5 h stirring at ambient temperature, removal of the volatile solvent gave the
crude N-(c«-4-amino-cyC1-5hexylmethyl)-3,5-bistrifluoromethyl-benzamide trifluoroacetate as a
sticky oil. After addition of water (-40 mL) to the crude product, 5-10 min shaking provided
formation of precipitates. The ppts were filtered, washed with water, and dried. 1.40 (61 %) of N-
(czs-4-amino-cyclohexylmethyl)-3,5-bistrifluoromethyl-benzamide trifluoroacetate was isolated as
a white powder.
ESI MS m/e 369 (M + H)+; ]H NMR (400 MHz, DMSO-d6) 5 8.97 (bs, 1 H), 8.47 (s, 2 H), 8.29 (s,
1 H), 7.78 (bs, 3 H), 3.29 (t, 2 H, J = 6.8 Hz), 3.15 (bs, 1 H), 1.78 (bs, 1 H), 1.66 (m, 4 H), 1.52 (m,
4H).
Step B: Synthesis of 7V-[(c(5-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-
yl]amino}cyclohexyl)methyl]-3,5-bis(trifluoromethyl)benzamide hydrochloride.
A sealed tube containing 2-chIoro-4-dimethylamino-5-methylpyrimidine (0.21 g, 1.2
mmol), N-(as-4-amino-cyclohexyImethyl)-3,5-bistrifluoromethyI-benzamide trifluoroacetate (0.6
g, 1 eq.), DIEA (0.45 mL, 2 eq.), and tert-BuOH (2.5 mL) was reacted for 1.6 h at 185 °C in a
Smith microwave synthesizer. The reaction was diluted with DC1-5, washed with diluted HC1 and
water, dried, and concentrated. The crude product was purified by column chromatography (silica
gel; DC1-5rMeOH = 100:0 to 95:5). 0.3 g (50 %) of N-[cjs-4-(4-dimethylamino-5-methyl-
pyrimidin-2-ylamino)-cyclohexylmethyl]-3,5-bistrifIuoromethyl-benzamide was isolated.
To a solution of neutral compound in DC1-5 (10 mL) was added 4M-HC1 in dioxane (0.3
mL, 2 eq.). After 30 min stirring at ambient temperature, removal of the volatile solvent provided
A^(c/s-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino} cyclohexyl)methyl]-3,5-
bis(trifluoromethyl)benzamide hydrochloride as a white powder. ESI MS m/e 504 (M + H)+; 'H
NMR (400 MHz, CDC13) 5 12.5 (bs, 1 H), 8.79 (d, 1 H, J = 8.0 Hz), 8.43 (s, 2 H), 7.93 (s, 1 H),
7.50 (bs, 1 H), 7.15 (d, 1 H, J - 4.4 Hz), 4.23 (bs, 1 H), 3.51 (bs, 2 H), 3.27 (s, 6 H), 2.23 (s, 3 H),
1.89-1.82 (m, 5 H), 1.66-1.60 (m, 4 H).

523
Example 2590
Ar-[(m-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]ainino}cyC1-5hexyl)methyl]-4-
(trifluoromethoxy)benzamide trifluoroacetate
Step A: Synthesis of Ar-[a5-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylainino)-
cyclohexylmethylj-carbamic acid benzyl ester.
Six sealed tubes, each containing 2-chIoro-4-dimethylamino-5-methyl pyrimidine (0.4 g,
2.3 mmoi), c/5-(4-amino-cyclohexylmethyl)-carbamic acid benzyl ester (0.61 g, 1 eq.), DIEA (0.8
mL, 2 eq.), and t-BuOH (2.5 mL), were reacted in a Smith microwave synthesizer for 6500 sec at
185 °C. Completion of the reaction was confirmed by LC-MS. The combined reaction was diluted
with DC1-5, washed with 1N-HCI (2 x) and water (1 x), and dried with anhydrous MgSO-t. The
organic was concentrated and purified by column chromatography (silica gel; hexane: DC1-5:
MeOH = 1:5:0 to 0:95:5). Removal of the solvent gave 3.2 g (58 %) of N-[cisA-(4-
dimethylamino-5-methyI-pyrimidin-2-yiamino)-cyclohexylmethyl]-carbamic acid benzyl ester.
ESI MS m/z 398 (M + H)+; *H NMR (400 MHz, CDC13) 5 8.00 (bs, 1 H), 7.36 (m, 6 H), 5.10 (s, 3
H, NH-was overlapped), 4.12 (bs, 1 H), 3.24 (s, 6 H), 3.14 (t, 2 H, J = 6.4 Hz), 2.22 (s, 3 H),
1.88-1.50 (m, 9 H).
Step B: Synthesis of jV-[c/$-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexylmethyl] amine.
The heterogenous mixture of 7V-[cw-4-(4-dimethylamino-5-methyI-pyrimidin-2-ylamino)-
cyclohexylmethylj-carbamic acid benzyl ester (3.0 g, 7.5 mmol) and 10 % Pd/C (0.12 g) in EtOH
(20 mL) was stirred overnight under H2 atmosphere at room temperature. Cbz of all starting
material was cleaved, which was confirmed by ESI MS. The reaction was filtered through a pad of
celite, and the organic was concentrated and purified by column chromatography (silica gel,
DC1-5:MeOH = 100:0 to 80:20). 1.5 g (75 %) of 7V-[c/5-4-(4-dimethylamino-5-methyl-pyrimidin-2-

524
ylamino)-cyclohexylmethyl] amine was isolated as a yellowish powder.
ESI MS m/z 264 (M + H)+; lH NMR (400 MHz, DMSO-d6) ( 7.70 (bs, 2 H), 7.60 (s, 1 H), 6.05 (d,
1 H, J - 6.4 Hz), 3.89 (bs, 1 H), 2.96 (s, 6 H), 2.71 (d, 2 H, J = 6.8 Hz), 2.08 (s, 3 H), 1.70-1.45 (m,
9H).
Step C: Synthesis of ^-[(^-^{[^(dimethylamino^S-methylpyrimidin^-
yI]amino}cyclohexyl)niethyl]-4-(trifIuoroinethoxy)benzamide trifluoroacetate.
To a solution of N-[c/5-4-(4-dimethyIamino-5-methyI-pyrimidin-2-ylamino)-
cyclohexylmethyl] amine (25 mg, 0.01 mmol) in DC1-5 (1.0 mL) was added 4-
trifluoromethoxybenzoyl chloride (21 mg, leq.), and followed by Et3N (30 (L). The reaction was
stirred for 4h at room temperature, concentrated, and purified by prep-HPLC. 20 mg (38 %) of A"-
[(c/5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)methyl]-4-
(trifluoromethoxy)benzamide trifluoroacetate was isolated as a white powder.
ESI MS m/z 452 (M + H)+; 1H NMR (400 MHz, CDC13) ( 13.9 (bs, 1 H), 8.36 (bd, 1 H, J - 6.4
Hz), 7.88 (d, 2 H, J = 8.4 Hz), 7.27 (s, 1 H), 7.23 (d, 2 H, J = 8.4 Hz), 7.08 (bs, 1 H), 4.17 (bs, 1 H),
3.42 (t, 2 H, J = 5.6 Hz), 3.28 (s, 6 H), 2.23 (s, 3 H), 1.91-1.78 (m, 3 H), 1.65-1.55 (m, 6 H).
Example 2591
3,5-Dichloro-7V-[c/s-4-({[4-(diinethylainino)-5-methyIpyrimidin-2-yl]aniino}-
methyl)cyclohexyl] benzamide trifluoroacetate
Step A: Synthesis of Ar-c/y-4-[(4-dimethylamino-5-methyl-pyrimidin-2-yIamino)-methylJ-
cyclohexylamine.
Six sealed tubes, each containing 2-chloro-4-dimethylamino-5-methyl pyrimidine (0.4 g,
2.3 mmol), ci5-(4-aminomethyl-cyclohexyl)-carbamic acid tert-buty\ ester (0.53 g, 1 eq.), DIEA
(0.7 mL, 2 eq.), and t-BuOH (2 mL), were reacted in a Smith microwave synthesizer for 7000 sec
at 185 °C. ESI MS confirmed that all starting material was consumed. The reactions were

525
combined, diluted with DC1-5 and washed with 1N-HC1 (2 x) and water (1 x). The organic was
concentrated and carried to the next step without a further purification.
The crude iV-{c/5-4-[(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-methyl]-
cyclohexyl}-carbamic acid tert-buty\ ester was dissolved in DC1-5 (15 mL), and TFA (10 mL) was
added. After 1.5 h stirring, removal of the volatile solvent gave 7V-c/5-4-[(4-dimethylamino-5-
methyl-pyrimidin-2-ylamino)-methyl]-cyclohexylamine trifluoroacetate as a sticky oil. The sticky
oil was treated with sat. NaOH (15 mL), and the basic aqueous layer was extracted with DC1-5 (2 x)
to remove nonpolar organic impurity, and the aqueous was concentrated to give a solid residue.
The solid residue was extracted several times with DC1-5/MeOH (3/1), and removal of the solvent
provided neutral iV-c/5-4-[(4-dimethylamino-5-methyl-pyrimidin-2-ylarnino)-methyl]-
cyclohexylamine (1.5 g, 41 %) as a yellowish powder.
ESI MS 264 (M + H)+; 'H NMR (400 MHz, CDC13) 5 7.60 (s, 1 H), 5.05 (bs, 1 H), 3.29 (t, 2 H, J =
6.4 Hz), 3.03 (s, 7 H, CH-NH2 was overlapped), 2.54 (bs, 2 H), 2.13 (s, 3 H), 1.72 (bm, 1 H),
1.59-1.45 (m, 8 H).
Step B: Synthesis of 3,5-dichIoro-Ar-[c/y-4-({(4-(diinethylainino)-5-methylpyriniidin-2-
yl]amino}methyl)cyclohexyl]benzamide trifluoroacetate.
To a solution of A^-c/5-4-[(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-methyl]-
cyclohexylamine (28 mg, 0.01 mmol) in benzene/DC1-5 (2/1, 1.5 mL) was added 3,5-
dichlorobenzoyl chloride (22 mg, leq.), and followed by Et3N (30 \xL). The reaction was stirred
for3h at room temperature, concentrated, and purified by prep-HPLC. 30mg(51 %) of 3,5-
dichloro-Ar-[c/5-4-( {[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}methyl)cyclohexyl]benzamide trifluoroacetate was isolated as a white powder.
ESI MS m/e 436 (M + H)+; 'H NMR (400 MHz, CDC13) 5 13.7 (bs, 1 H), 8.71 (bs, 1 H), 7.61 (d, 2
H, J = 1.6 Hz), 7.44 (t, 1 H, J = 1.6 Hz), 7.29 (s, 1 H), 6.59 (d, 1 H, J = 6.4 Hz), 4.23 (bm, 1 H),
3.36 (t, 2 H, J - 6.0 Hz), 3.29 (s, 6 H), 2.24 (s, 3 H), 1.81 (m, 3 H), 1.68 (m, 4 H), 1.45 (m, 2 H).

526
Example 2592
A^fC1-5^-df^Dimethylamino^-methylpyrimidin^-ylJaminoJmethylJcyclohexylJ-S^-
bis(trifluoromethyl)benzamide trifluoroacetate
Step A: Synthesis of Ar-c/y-4-[(4-dimethylamino-6-methyl-pyrimidin-2-yIamino)-methyl]-
cyclohexylamine.
Six sealed tubes, each containing 2-chloro-4-dimethyIamino-6-methyl pyrimidine (0.4 g,
2.3 mmol), c/s-(4-aminomethyl-cyclohexyl)-carbamic acid tert-buty\ ester (0.53 g, 1 eq.), DIEA
(0.7 mL, 2 eq.), and t-BuOH (2 mL), were reacted in a Smith microwave synthesizer for 6500 sec
at 185 °C. The reaction was monitored by LC-MS. The combined reaction was diluted with DC1-5
and washed with 1N-HC1 (2 x) and water (1 x). The organic was concentrated and performed
deprotection without a further purification.
To a solution of A^-{c/5-4-[(4-dimethyIamino-6-methyI-pyrimidin-2-ylamino)-methyl]-cyclohexyl}-
carbamic acid ter/-butyl ester in DC1-5 (15 mL) was added TFA (10 mL). The reaction was stirred
for 1.5 h at room temperature, and removal of the volatile solvent gave JV-C/S-4-[(4-dimethylamino-
6-methyI-pyrimidin-2-ylamino)-methyI]-cyclohexylamine trifluoroacetate as a sticky oil. The
sticky oil was treated with sat. NaOH (15 mL), and the basic aqueous layer was extracted with
DC1-5 (2 x), and the aqueous was concentrated to give a solid residue. The solid residue was
extracted several times with DC1-5/MeOH (3/1), and removal of the solvent provided neutral TV-c/s-
4-[(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-methyl]-cyclohexylamine (2.1 g, 57 %) as a
yellowish powder.
ESI MS m/e 264 (M + H)~; 1H NMR (400 MHz, CDC13) 5 5.91 (bs, 1 H), 5.65 (s, 1 H), 3.33 (t, 2 H,
J = 6.4 Hz), 3.06 (s, 6H),2.97(m, 1 H), 2.27 (bs, 2 H), 2.11 (s, 3 H), 1.70 (m, 1 H), 1.59-1.45 (m,
8H).
Step B: Synthesis of Ar-[c«-4-({[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-
methyl)cyclohexylJ-3,5-bis(trifluoromethyl)benzamide trifluoroacetate.
To a solution of Ar-cw-4-[(4-dimethylamino-6-methyI-pyrimidin-2-ylamino)-methyl]-

527
cyclohexylaraine (20 mg, 0.008 mmol) in benzene/DC1-5 (2/1, 1.5 mL) was added 3,5-
bistrifluoromethyibenzoyl chloride (21 mg, leq.), and followed by Et3N (30 (iL). The reaction was
stirred for 3h at room temperature, concentrated, and purified by prep-HPLC. 25 mg (53 %) of A"-
[czs-4-({[4-(dimethy]amino)-6-methylpyrimidin-2-yl]amino} methyI)cyclohexyl]-3,5-
bis(trifluoromethyl)benzamide trifluoroacetate was isolated as a white powder.
ESI MS m/e 504 (M + H)+; !H NMR (400 MHz, CDC13) 8 13.9 (bs, 1 H), 8.86 (bs, 1 H), 8.25 (s, 2
H), 7.96 (s, 1 H), 7.30 (d, 1H,J = 6.4 Hz), 5.74 (s, 1 H), 4.40 (bm, 1 H), 3.42 (t, 2 H, J - 6.0 Hz),
3.26 (s, 3 H), 3.13 (s, 3 H), 2.33 (s, 3 H), 1.91-1.60 (m, 9 H).
Example 2593
4-Chloro-Ar-[(c/5-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)~
m ethyl] benzam id e trifluoroacetate
Step A: Synthesis of N-[c/s-4-(4-dimethylamino-6-methyI-pyrimidin-2-ylamino)-
cyclohexylmethylj-carbamic acid benzyl ester.
Six sealed tubes, each containing 2-chloro-4-dimethylamino-6-methyl pyrimidine (0.4 g,
2.3 mmol), c/5-(4-amino-cyclohexylmethyl)-carbamic acid benzyl ester (0.61 g, 1 eq.), DIEA (0.8
mL, 2 eq.), and t-BuOH (2.5 mL), were reacted in a Smith microwave synthesizer for 6500 sec at
180 °C. The combined reaction was diluted with DC1-5, washed with 1N-HC1 (2 x) and water (1 x),
dried with MgSO4, and concentrated. Purification by column chromatography (silica gel; hexane:
DC1-5: MeOH = 1:5:0 to 0:95:5) gave 4.8 g (86 %) ofN-[c/s-4-(4-dimethylamino-6-methyl-
pyrimidin-2-ylamino)-cyclohexylmethyl]-carbamic acid benzyl ester.
ESI MS m/z 398 (M + H)+; 'H NMR (400 MHz, CDCI3) 5 8.40 (bs, 1 H), 7.38 (m, 5 H), 5.70 (s, 1
H), 5.10 (s, 3 H, NH-was overlapped), 4.17 (bs, 1 H), 3.14 (bs, 6 H), 3.12 (t, 2 H, J - 6.0 Hz), 2.32
(s,3H), 1.90-1.50 (m, 9 H).
Step B: Synthesis of Ar-[c«-4-(4-dimethylamino-6-methyI-pyrimidin-2-ylamino)-

528
cyclohexylmethyl] amine.
The heterogenous solution of iV-[c/5-4-(4-dimethylamino-6-methy]-pyrimidin-2-ylamino)-
cyclohexylmethyl]-carbarn ic acid benzyl ester (4.5 g, 11.3 mmol) and 10 % Pd/C (0.20 g) in EtOH
(25 mL) was stirred overnight under H2 atmosphere at room temperature. The reaction was filtered
through a pad of celite, and the organic was concentrated and purified by column chromatography
(silica gel, DC1-5:MeOH = 100:0 to 80:20). 2.2 g (76 %) of #-[cw-4-(4-dimethylamino-6-methyl-
pyrimidin-2-ylamino)-cyclohexylmethyl] amine was isolated as a yellowish powder.
ESI MS m/e 264 (M + H)+; 'H NMR (400 MHz, CDC13) 6 7.82 (bs, 1 H), 5.72 (s, 1 H), 4.40 (bs, 2
H), 4.15 (bm, 1 H), 3.16 (s, 6 H), 2.84 (d, 2 H, J = 6.8 Hz), 2.32 (s, 3 H), 1.80 (m, 2 H), 1.70-1.45
(m,7H).
Step C: Synthesis of 4-chloro-7V-[(c*5-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-
yl]amino}cyclohexyl) methyl]benzamide trifluoroacetate.
To a solution of Ar-[c;5-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-
cyclohexylmethyl] amine (25 mg, 0.01 mmol) in DC1-5/benzene (3/1, 1.0 mL) was added 4-
chlorobenzoyl chloride (17 mg, leq.), and followed by Et3N (30 \iL). The reaction was stirred for
4h at room temperature, concentrated, and purified by prep-HPLC. 25 mg (51 %) of 4-chloro-iV-
[(c/.v-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino} cyclohexyl)methyl]benzamide
trifluoroacetate was isolated as a white powder.
ESI MS m/e 402 (M + H)+; !H NMR (400 MHz, CDC13) 6 13.8 (bs, 1 H), 8.60 (bd, 1 H, J = 6.4
Hz), 7.78 (d, 2 H, J = 8.4 Hz), 7.35 (d, 2 H, J = 8.4 Hz), 7.03 (bm, 1 H), 5.71 (s, 1 H), 4.20 (bs, 1
H), 3.42 (t, 2 H, J = 6.0 Hz), 3.22 (s, 3 H), 3.10 (s, 3 H), 2.31 (s, 3 H), 1.91-1.78 (m, 3 H),
1.65-1.55 (m, 6 H).
Example 2594
c/5-4-{[4-(DimethyIamino)-5-methylpyrimidin-2-yl]amino}-A'-[(15)-l-(4-niethyl-
phenyl)ethyl]cyclohexaneearboxamide hydrochloride

529
Step A: Synthesis of c/s-4-(4-dimethylamino-5-methyl-pyriniidin-2-ylamino)-
cyclohexanecarboxylic acid ethyl ester.
A sealed tube containing a suspension of 2-chloro-4-dimethylamino-5-methylpyrimidine
(0.28 g, 1.6 mmol), c/5-4-amino-cyC1-5hexanecarboxylic acid ethyl ester hydrochloride (0.33 g, 1
eq.), DIEA (0.65 mL, 2 eq.) in IPA (2 mL) was reacted in a Smith microwave synthesizer for 1
hour at 155" C. The solution was diluted with DC1-5, washed with 1N-HCI and water, concentrated,
and purified by flash chromatography (silica gel, 1% MeOH in CH2Ci2) to give cw-4-(4-
dimethylamino-5-methyl-pyrimidin-2-ylamino) cyclohexanecarboxylic acid ethyl ester (0.3 g,
60 %) as a pale yellow solid.
ESI MS m/e 307 (M + H)+; *H NMR (400 MHz, CDC13) 5 7.66 (s, 1 H), 4.72 (bd, 1 H, J = 6.8 Hz),
4.13 (q, 2 H, J = 6.8 Hz), 3.96 (bs, 1 H), 3.01 (s, 6 H), 2.44 (m, 1 H), 2.13 (s, 3 H), 1.89 (m, 2H),
1.72 (m, 6 H), 1.25 (t, 3 H, J = 6.8 Hz).
Step B: Synthesis of c/s-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexanecarboxylic acid.
A suspension of c/5-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)
cyclohexanecarboxylic acid ethyl ester (0.25 g, 0.8 mmol) in 4N-HC1 (10 mL) was stirred for 4 h at
85 °C. Progress of the reaction was monitored by LC-MS. The reaction was cooled to room
temperature and completely removed the volatile solvent under a vacuum to give cw-4-(4-
dimethylamino-5-methyl-pyrimidin-2-ylamino) cyclohexanecarboxylic acid (0.2 g, 90 %) as a
white powder.
ESI MS m/e 279 (M + H)+; lH NMR (400 MHz, CDC13) 5 7.95 (bs, 1 H), 7.43 (s, 1 H), 3.94 (bs, 1
H), 3.28 (bs, 6 H), 2.49 (bs, 1 H), 2.25 (s, 3 H), 2.04 (m, 2 H), 1.82 (m, 2 H), 1.73 (m, 4 H), COOH
was not observed.
Step C: Synthesis of cw-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-iV-[(llS)-l-(4-
methylphenyl)ethyl]cyclohexanecarboxamide hydrochloride.

530
To a suspension of (S^l-^-methylphenyO-ethylamine (12 mg, 1 eq.) and cw-4-(4-
dimethyIamino-5-methyl-pyrimidin-2-y]amino) cyclohexanecarboxylic acid (24 mg, 0.09 mmol) in
DC1-5 (2 mL) was added HATU (36 mg, 1.1 eq.). The reaction stirred for 30 seconds at room
temperature under argon, and triethylamine (5 drops) was added. The reaction stirred overnight at
room temperature. The reaction was diluted with DC1-5, washed with saturated NaHCO3 (2x) and
H2O (lx), and concentrated. Purification by column chromatography (silica gel; DC1-5:MeOH =
100:0 to 94:6) gave c/5-4-(4-Dimethylamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexanecarboxylic acid (S)-(l-p-tolyl-ethyl)-amide (15 mg, 43 %). To a solution of the amide
in DC1-5 (1 mL) was added 4M-HC1 in dioxane (50 uL). The reaction was stirred for 30 min at
room temperature, and removal of the volatile solvent gave c/5-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}-N-[(l,S)-l-(4-methylphenyl)ethyI]cyclohexanecarboxamide
hydrochloride as a white powder.
ESI MS m/e 396 (M + H)+; *H NMR (400 MHz, DMSO-^) 5 11.0 (bs, 1 H), 8.14 (d, 1 H, J = 8.4
Hz), 7.68 (bs, 1 H), 7.54 (s, 1 H), 7.14 (d, 2 H, J = 8.0 Hz), 7.07 (d, 2 H, J = 8.0 Hz), 4.84 (m, 1 H),
4.01 (bs, 1 H), 3.24 (s, 6 H), 2.27 (m, 1 H), 2.25 (s, 3 H), 2.22 (s, 3 H), 1.80-1.54 (m, 8 H), 1.29 (d,
3H,J-6.8Hz).
Example 2595
2,2-Difluoro-Ar-(C1-5-4-{I5-methyl-4-(methylamino)pyrimidin-2-yl]amino}cyclohexyl)-l,3-
benzodioxole-5-carboxamide trifluoroacetate
Step A: Synthesis of 2,2-difluoro-iV-(c/$-4-{[5-methyl-4-(methylamino)pyrimidin-2-
yl]amino}cyclohexyl)-l^-benzodioxole-5-carboxamide trifluoroacetate.
2-(3,5-Dimethoxy-4-formyl)phenoxy ethyl polystyrene resin (1.0 gram; 0.94mmol/gram)
and methylamine (0.0122 mol) in 15 mL of CH2C12 was suspended in a fritted synthesis flask. To
this suspension was added a solution of NaBH(OAc)3 (0.0122 mol) in CH2C12 (15 mL). After
shaking the mixture overnight in a rotary shaker, the solution was removed by filtration. The

531
resulting resin bound N-methylamine was washed sequentially with CH2C12, DMF, and MeOH.
The washing sequence was repeated four times. The resin bound N-methylamine was dried under
vacuum for 20 minutes.
The resin bound Nmethylamine was suspended in DMF (10 mL). To the resin suspension
was added 2,4-dichloro-5-methyl-pyrimidine (1.41 mmol) followed by triethylamine (0.393 mL,
2.82 mmol). The reaction mixture was shaken at 40 °C overnight. The solution was removed by
filtration and the resin washed sequentially with DMF, CH2C12 and MeOH. The wash sequence was
repeated four times. The resulting resin bound intermediate was dried under vacuum for 20 minutes
The resin bound intermediate was divided up into three portions and each portion was
transferred into a 5ml Smith synthesizer reaction vessel. The resins (0.282 mmol) were separately
suspended in a 1:1 solution of IPA/H?0 (3 mL). To each suspension was added cw-l,4-diamino-
cyclohexane (0.85 mmol) and DIEA (0.295ml; 1.69 mmol). The reactions were heated in a
microwave synthesizer at 180°C for 4.5 hours. The resins were pooled together; and the solution
removed by filtration. The resin was sequentially washed with IPA, H2O, MeOH, CH2C12, and
MeOH. The washing sequence was repeated three times. The resulting resin bound intermediate
was dried under vacuum for 20 minutes.
The resin bound intermediate was suspended in DMF (10ml). To the resin suspension
was added the 2,2- diflouro-benzo[l,3]dioxole 5-carbonyl chloride (0.94 mmol) and triethylamine
(0.256 mL; 1.88 mol). The reaction was shaken in a rotary mixer at room temperature for 45
minutes. The solution was removed by filtration and the resin washed sequentially with DMF,
CH?C12, MeOH. The wash sequence repeated three times.
After drying under vacuum for 20 minutes, the resin was treated with 15 mL of TFA
solution (TFA /CH2C12 /H20 20:20:1 v/v). The reaction was shaken for 2 hours and the TFA
solution was collected after filtration. The TFA was removed by rotary evaporation and the
compound subjected to purification by preparative HPLC to give 2,2-difluoro-/V-(cw-4-{[5-methyl-
4-(methylamino)pyrimidin-2-yl]amino} cyclohexyI)-l,3-benzodioxole-5-carboxamide
trifluoroacetate (8.6 mg, 5%) as a white solid.
ESI MS m/e 420.5 M+Yf; lU NMR (400MHz, CD3OD) 5 8.21 (d, J= 4 Hz, 1H), 7.75-7.67 (m,

532
2H), 7.41 (s, 1H), 7.28 (d, J= 8 Hz, 1H), 3.99 (m, 2H), 3.05 (s, 3H), 1.99 (s, 3H), 1.95-1.71 (m,
8H).
Example 2596
5-Bromo-7V-(cw-4-{[5-methyl-4-(methylamino)pyrimidin-2-yI]amino}cyclohexyl)-2-furamide
trifluoroacetate
Step A: Synthesis of 5-bromo-Ar-(c/s-4-{[5-methyl-4-(methyIamino)pyrimidin-2-
yl]amino}cyclohexyl)-2-furamide trifluoroacetate.
Using the procedure of Example 2595, the title compound was obtained.
ESI MS m/e 408.2 M+rT; ]H NMR (400MHz, CD3OD) 5 7.41 (s, 1H), 7.10 (s, 1H), 6.60 (s, 1H),
4.08-3.97 (m, 2H), 3.05 (s, 3H), 1.99 (s, 3H), 1.95-1.71 (m, 8H).
Example 2597
3,5-Dibromo-Ar-(cw-4-{[5-methyl-4-(methylamino)pyrimidin-2-yl]amino}cydohexyl)-
benzamide trifluoroacetate
Step A: Synthesis of 3,5-dibromo-7V-(m-4-{E5-methyl-4-(methylamino)pyrimidin-2-
yl]amino}cyclohexyl)benzamide trifluoroacetate.
Using the procedure of Example 2595, the title compound was obtained.
ESI MS m/e 496.2 M+tT; 'H NMR (400MHz, CD3OD) 5 8.37 (m, J= 4 Hz, 1H), 8.02-7.91 (m,
3H) 7.41 (s, 1H), 4.12 -3.97 (m, 2H), 3.05 (s, 3H), 1.99 (s, 3H), 1.95-1.71 (m, 8H).
Example 2598
3-Fluoro-Ar-(c/5-4-{I5-methyl-4-(methylamino)pyrimidin-2-yl]ainino}cyclohexyl)-5-

(trifiuoromethyl)benzamide trifluoroacetate
Step A: Synthesis of 3-fluoro--/V-(cw-4-{[5-methyl-4-(inethylainino)pyrimidin-2-
yl]amino}cyclohexyl)-5-(trifluoromethyl)benzamide trifluoroacetate.
Using the procedure of Example 2595, the title compound was obtained.
ESI MS m/e 426.4 M+H+; 'H NMR (400MHz, CD3OD) 5 8.02 (m, 1H), 7.98 (d, J= 4 Hz, 1H)
7.68 (d,/= 4 Hz 1H), 7.43-7.41 (s, 1H)4.31 -3.81 (m,2H), 3.05 (s,3H), 1.87(s,3H), 1.87-1.73 (m,
8H).
Example 2599
Ar-(as-4-{[5-Methyl-4-(niethylamino)pyrimidin-2-yllamino}cyclohexyl)-4-
(trifluoromethoxy)benzamide trifluoroacetate
Step A: Synthesis of Ar-(c/s-4-{[5-methyl-4-(methylamino)pyrimidin-2-yl]amino}cyclohexyl)-
4-(trifluoromethoxy)benzamide trifluoroacetate.
Using the procedure of Example 2595, the title compound was obtained.
ESI MS m/e 424.3 M+H"; 'H NMR (400MHz, CD3OD) 5 8.34 (d, J= 4 Hz, 1H), 7.85 (d, J= 8 Hz,
1H) 7.72 -7.55 (s, 1H), 7.47-7.31 (m, 3H), 4.31 -3.82 (m, 2H), 3.05 (s, 3H), 1.98 (s, 3H), 1.96-1.72
(m, 8H).
Example 2600
Ar-(cw-4-{[5-methyl-4-(methylamino)pyrimidin-2-yI]amino}cyclohexyl)-3,5-
bis(trifluoromethyl)benzamide hydrochloride
Step A: Synthesis of 7V-(c«-4-{[5-methyl-4-(methylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-
3,5-bis(trifluoromethyl)benzamide hydrochloride.

534
To a solution of (2-chloro-5-methyl-pyrimidin-4yl)-methyl-amine (200mg, 1.27 mmol) in
lmL 2-propanol was added cw-jV-(4-amino-cyclohexyl)-3,5-bis-trifluoromethyl-benzamide (676mg,
1.9lmmol)and DIEA (2.54mmol). The mixture was heated in a microwave synthesizer at 180 °C
for 2 hours. The solvent was evaporated and the material subjected to chromatography (70 ~ 95%
ethyl acetate/ hexanes) The combined compound in CH2C12 was added 2 M HC1 in diethyl ether
(1.5ml, 0.38mmol). The solvents were removed in vacuo to yield W-(cw-4-{[5-methyl-4-
(methylamino)pyrimidin-2-yl]amino} cyclohexyl)-3,5-bis(trifluoromethyl)benzamide
hydrochloride (385.5mg, 0.75mmol, 59 %) as awhile solid.
ESI MS 476.2 M+H*; 'H NMR (400 MHz, DMSO-d6) 5 11.7 (s, 1H), 8.64 (s, 1H), 8.35 (s, 2H),
8.14 (s, 1H), 8.09 (bs, 1H), 8.00 (bs, 1H), 7.45 (s, 1H), 3.83 (bs, 1H), 3.75 (bs, 1H), 3.20 (s, 3H),
2.77-2.76 (d, J= 4 Hz, 3H), 1.76 (m, 2H), 1.58 (m, 6H).
Example 2601
Ar-(cw-4-{[4-(Ethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3,4-difluorobenzamide
trifluoroacetate
Step A: Synthesis of Ar-(ciy-4-{[4-(ethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3,4-
difluorobenzamide trifluoroacetate.
Using the procedure of Example 2595, the title compound was obtained.
ESI MS m/e 390.4 M+tf; !H NMR (400MHz, CD3OD) 5 8.22 (d, J= 4 Hz, 1H), 7.78 (m, 1H),
7.68 (m, lH),7.42(s, lH),7.38(m, 1H), 4.22-3.99 (m, 2H), 3.63-3.56 (quartet, J= 4 Hz, 2H), 1.99
(s, 3H), 1.93-1.81 (m, 8H), 1.29-1.19 (t, J= 8 Hz, 3H).
Example 2602
3,4-Difluoro-Ar-(ds-4-{[4-(isopropylamino)-5-methylpyrimidin-2yl]amino}cyclohexyl)-
benzamide trifluoroacetate

535
Step A: Synthesis of 3,4-difluoro-yV-(c/>-4-{[4-(isopropylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide trifluoroacetate.
Using the procedure of Example 2595, the title compound was obtained.
ESI MS m/e 404.4 M+H+; 'HNMR(400MHz, CD3OD) 6 8.10 (m, 1H), 7.80-7.75(m, 1H), 7.68
(m, 1H), 7.42 (s, 1H), 7.39-7.34 (m, 1H), 4.28-4.07 (m, 3H), 2.03 (s, 3H), 1.99-1.79 (m, 8H), 1.31-
1.26(d,J=12Hz,6H).
Example 2603
Ar-(m-4-{[4-(cyclopropylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-3,4-
difluorobenzamide trifluoroacetate
Step A: Synthesis of Ar-(c«-4-{[4-(cyC1-5propylamino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)-3,4-difluorobenzamide trifluoroacetate.
Using the procedure of Example 2595, the title compound was obtained.
ESI MS m/e 402.2 M+rF; ]HNMR (400MHz, CD3OD) 5 7.78-7.73 (m, 1H), 7.69-7.66 (m, 1H),
7.42 (s, 1H), 7.40-7.33 (m, 1H), 4.26-3.88 (m, 2H), 3.02-2.96 (m, 1H), 1.97-1.81 (m, 11H), 0.90-
0.85 (m, 2H), 0.72-0.68 (m, 2H).
Example 2604
3,4-Difluoro-N-(cw-4-{[5-methyl-4-(methylamino)pyrimidin-2-yl]amino}cyclohexyl)-
benzamide trifluoroacetate
Step A: Synthesis of 3,4-difluoro-N-(ciy-4-{[5-methyl-4-(methylamino)pyrimidin-2-
yl]amino}cyclohexyl)benzamide trifluoroacetate.
Using the procedure of Example 2595, the title compound was obtained.

536
T+. ll
ESI MS m/e 376.2 M+H ; 'H NMR (400MHz, CD3OD) 5 7.80-7.75 (m, 1H), 7.68 (m, 1H), 7.43-
7.35 (m, 2H), 4.31-4.06 (m, 2H), 3.05 (s, 3H), 2.04 (s, 3H), 1.99-1.75 (m, 8H).
Example 2605
2-(3,4-Dichlorophenoxy)-N-(c/s-4-{[5-methyl-4-(methylamino)pyrimidin-2-
yl]amino}cyclohexyi)acetamide trifluoroacetate
Step A: Synthesis of 2-(3,4-dichlorophenoxy)-N-(cK-4-{[5-methyl-4-(methylamino)-
pyrimidin-2-yl]amino}cyclohexyl)acetamide trifluoroacetate.
Using the procedure of Example 2595, the title compound was obtained.
ESI MS m/e 438.3 M+H"; *H NMR (400MHz, CD3OD) 5 7.45-7.40 (m, 2H), 7.20 (s, 1H), 6.97-
6.94 (m, 1H), 4.55 (s, 2H), 3.92-3.34 (s, 2H) 3.04 (s, 3H), 1.98 (s, 3H), 1.53-1.71 (m, 8H).
Example 2606
2-(2,3-Dichlorophenoxy)-N-(as-4-{[5-methyl-4-(methylamino)pyrimidin-2-
yl]amino}cyclohexyl)acetamide trifluoroacetate
Step A: Synthesis of 2-(2r3-dichIorophenoxy)-N-(cis-4-{[5-methyl-4-(methylamino)-
pyrimidin-2-yl]amino}cyclohexyl)acetamide trifluoroacetate.
Using the procedure of Example 2595, the title compound was obtained.
ESI MS m/e 438.3 M+H+; lHNMR (400MHz, CD3OD) 8 7.42 (s, 1H), 7.31-6.92 (m, 3H), 4.65 (s,
2H), 4.07-3.95 (m, 2H), 3.05 (s, 3H), 1.98 (s, 3H), 1.93-1.69 (m, 8H).
Example 2607
N-(ci5-4-{[4-(Dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)benzamide

537
trifluoroacetate
Step A: Synthesis of 2,4-dichloro-5,6-dimethyl-pyriinidine.
To a suspension of 2,4-dihydroxy-5,6-dimethylpyrimidine (6.2 g, 0.044 mol) in POC13 (25
mL) was slowly added AyV-dimethylaniline (6.18 mL, 0.049 mol). The mixture was then refluxed
at 125 °C for 3 hours. After this time, the starting material completely dissolved indicating that the
reaction was completed. The reaction mixture was cooled and then poured slowly onto ice to
quench the POCb (caution exothermic!). A precipitate formed, which was filtered and washed
with ice-cold water. The precipitate was dried under high vacuum overnight to yield 2,4-dichloro-
5,6-dimethyl-pyrimidine (7.2 g, 0.041 mol, 92 %) as a yellow solid.
'H NMR (400 MHz, CDCb) 5 2.56 (s, 3H), 2.36 (s, 3H).
Step B: Synthesis of (2-chloro-5,6-dimethyl-pyrimidin-4-yl)-dimethyl-amine.
To a solution of 2,4-dichloro-5,6-dirnethyl-pyrimidine (0.2 g, 0.0011 mol) in 1 mL 2-
propanol was added DIEA (268 uL, 0.0017 mol) and dimethylamine (514 uL, 0.0010 mol). The
mixture was then heated in a microwave at 170 °C for 30 minutes. The reaction mixture was
cooled and concentrated and the resulting oil was purified by column (0-50% ethyl acetate in
hexanes) to yield (2-chloro-5,6-dimethyI-pyrimidin-4-yl)-dimethyl-amine (75 mg, 0.40 mmol,
40%) as a white solid.
ESI MS 186.0 M+H+ ; lHNMR (400 MHz, CDC13) 5 3.03 (s, 6H), 2.37 (s, 3H), 2.15 (s, 3H).
Step C: Synthesis of c/s-[4-(4-dimethylamino-5,6-dimethyl-pyrimidin-2-ylamino)-cyclohexyl]-
carbamic acid tert-buty\ ester.
To a solution of (2-chloro-5,6-dimethyl-pyrimidin-4-yl)-dimethyl-amine (0.5 g, 0.0027
mol) in 2 mL 2-propanol was added DIEA (514 uL, 0.0040 mol) and c/s-(4-amino-cyclohexyI)-
carbamic acid tert-buty\ ester (635 mg, 0.0030 mol). The mixture was then heated in a microwave
at 170 °C for 1 hour. The reaction mixture was cooled and concentrated and the resulting oil was
purified by column (0-100% ethyl acetate in hexanes) to yield ci5-[4-(4-dimethylamino-5,6-

538
dimethyl-pyrimidin-2-ylamino)-cyclohexyl]-carbamic acid tert-buty\ ester (875 mg, 2.4 mmol,
89 %) as a white solid.
ESI MS 364.6 M+H+ ; 'HNMR (400 MHz, CD3OD) 5 3.97 (m, 1H), 3.53 (m, 1H), 2.95 (s, 6H),
2.23 (s, 3H), 2.09 (s, 3H), 1.78-1.55 (m, 8H), 1.48 (s, 9H).
Step D: Synthesis of cjs-4-(4-dimethylamino-5,6-dimethyl-pyrimidin-2-ylamino)-l-
aminocyclohexane.
To a solution of c;5-[4-(4-dimethylamino-5,6-dimethyl-pyrimidin~2-ylamino)-cyC1-5hexyl]-
carbamic acid ter/-butyl ester (3.4 g, 0.0094 mol) in 40 mL CH2C12 was added TFA (1.4 mL, 0.019
mol). The solution was stirred at room temperature for 4 hours (or until the reaction was complete
as judged by TLC). The excess solvent was evaporated off and the resulting oil was dissolved in
30 mL CH7CI2. The organic layer was extracted with 30 mL of a dilute NaOH (aq) / NaHCO3 (aq)
solution (the aqueous layer was confirmed to remain basic during the extraction using pH paper
indicator). The aqueous layer was back extracted twice with CH2CI7 and the organic layers
combined, dried over MgSO4, and concentrated to yield c/s-4-(4-dimethylamino-5,6-dimethyl-
pyrimidin-2-ylamino)-l-aminocyclohexane (2.2 g, 0.0084 mo], 90%) as a white solid.
ESI MS 264.2 M+tT ; lH NMR (400 MHz, CD3OD) 5 3.99 (m, 1H), 2.95 (s, 6H), 2.80 (m, 1H),
2.23 (s, 3H), 2.09 (s, 3H), 1.84-1.67 (m, 6H), 1.52-1.49 (m, 2H).
Step E: Synthesis of N-(c/s-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2yl]amino}-
cyclohexyl)benzamide trifluoroacetate.
To a solution of cw-4-(4-dimethylamino-5,6-dimethyl-pyrimidin-2-ylamino)-l-
aminocyclohexane (30 mg, 0.11 mmol) in 0.5 mLDMF was added pyridine (13.8 uL, 0.17 mmol)
and benzoyl chloride (12.6 uL, 0.11 mmol). The reaction mixture was stirred overnight and then
0.5 mL of DMSO was added to the mixture. The compound was then subject to purification by
prep LC1-5S to yield A^cjs-4-{[4-(dimethylamino)-5,6-dimethyl pyrimidin-2-
yl]amino}cyclohexyl)benzamide trifluoroacetate (27 mg, 0.056 mmol, 52%) as a white solid TFA
salt.

539
ESI MS m/e 368.2 M+H* ; 'H NMR (400 MHz, CD3OD) 5 7.85-7.83 (m, 2H), 7.58-7.54 (m, 1H),
7.51-7.47 (m5 2H), 4.15 (m, 1H), 4.03 (m, 1H), 3.28 (s, 6H), 2.34 (s, 3H), 2.19 (s, 3H), 2.00-1.80
(m, 8H).
Example 2608
iV-(cw-4-{l4-(Dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethyl)benzamide trifluoroacetate
Step A: Synthesis of Ar-(ci$-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2yl]amino}-
cyclohexyl)-3-(trifluoromethyl)benzamide trifluoroacetate.
Using the procedure of Example 2607, the title compound was obtained as a white solid
TFA salt.
ESI MS m/e 436.4 M+H4 ; 'H NMR (400 MHz, CD3OD) 5 8.16 (s, 1H), 8.12 (d, 1H, J= 7.6 Hz),
7.89 (d, 1H, J= 8.0 Hz), 7.71 (t, 1H, J= 8.0 Hz), 4.16 (m, 1H), 4.05 (m, 1H), 3.28 (s, 6H), 2.34 (s,
3H), 2.20 (s, 3H), 2.00-1.82 (m, 8H).
Example 2609
Ar-(C1-5-4-{[4-(Dimethylainino)-5,6-diinethylpyrimidio-2-yl]ainino}cyclohexyl)-2-
hydroxynicotinamide trifluoroacetate
Step A: Synthesis of A^is-4-{(4-(dimethylamino)-5,6-dimethylpyrimidin-2yl]amino}-
cyclohexyl)-2-hydroxynicotinamide trifluoroacetate.
To a solution of ci5-4-(4-dimethylamino-5,6-dimethyl-pyrimidin-2-ylamino)-l-aminocyclohexane
(30 mg, 0.11 mmol) in 0.5 mL DMF was added 2-hydroxynicotinic acid (15 mg, 0.11 mmol),
DIEA (29.8 uL, 0.17 mmol), and HATU (52 mg, 0.14 mmol). The reaction mixture was stirred
overnight and then 0.5 mL DMSO was added to the mixture. The compound was then subject to

540
purification by prep LC1-5S to yield 7Vr-(c/5-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-
yl]amino}cyclohexyl)-2-hydroxy nicotinamide trifluoroacetate (17 mg, 0.034 mtnol, 31 %) as a
white solid.
ESI MS m/e 385.2 M+H+ ; 'H NMR (400 MHz, CD3OD) 8 8.53 (dd, 1H, Jx = 7.2 Hz, J2 = 2.0 Hz),
7.70 (dd, 1H, J, = 6.4 Hz, J2 = 2.0 Hz), 6.61 (t, 1H, J= 6.8 Hz), 4.37 (m, 1H), 4.01 (m, 1H), 3.28 (s,
6H), 2.33 (s, 3H), 2.19 (s, 3H), 1.98-1.72 (m, 8H).
Example 2610
S-Bromo-A^tcw-^ll^Cdimethylamino^S^dimethylpyrimidin-l-yljaminojcyclohexy^-Z-
furamide trifluoroacetate
Step A: Synthesis of 5-Bromo-jY-(cw-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
y]]amino} cyclohexyl)-2-furamide trifluoroacetate.
Using a similar procedure of Example 2609, the title compound was obtained as a white
solid TFA salt.
ESI MS m/e 436.2 M+H"; lH NMR (400 MHz, CD3OD) 3 7.15 (d, 1H, 7=3.6 Hz), 6.63 (d, 1H, J
= 3.2 Hz), 4.16 (m, 1H), 3.99 (m, 1H), 3.27 (s, 6H), 2.34 (s, 3H), 2.19 (s, 3H), 1.98-1.95 (m, 2H),
1.89-1.76 (m,6H).
Example 2611
7V2-{cw-4-[(3,5-Dimethoxybenzyl)aminolcyclohexyI}-Arl^V4,5,6-tetramethylpyrimidine-2,4-
d in mine bis-trifluoroacetate
Step A: Synthesis of Ar2-{c/s-4-[(3,5-dimethoxybenzyl)amino]cyclohexyl}-V^A/4,5,6-
tetramethylpyrimidine-2,4-diamine bis-trifluoroacetate.
To a solution of ci5-4-(4-dimethyiamino-5,6-dimethyl-pyrimidin-2-ylamino)-l-

541
aminocyclohexane (26.3 mg, O.I mmol) in 0.5 mL MeOH was added 3,5-dimethoxybenzaldehyde
(15.0 mg, 0.09 mmol). The mixture was stirred at room temperature for a half an hour and then
sodium triacetoxyborohydride (84.8 mg, 0.4 mmol) was added. The mixture was stirred at room
temperature overnight and then 0.5 mL of DMSO was added to the mixture. The compound was
then subjected to purification by prep LC1-5S to yield Ar2-{c«-4-[(3,5-
dimethoxybenzyl)amino]cyclohexyl}-^V4^V4,5,6-tetramethylpyrimidine-2,4-diaminebis-
trifluoroacetate (24 mg, 0.037 mmol, 42%) as a white solid TFA salt.
ESI MS m/e 414.6 M+Yf ; !HNMR (400 MHz, CD3OD) 5 6.71 (d, 2H, J = 2.0 Hz), 6.59 (t, 1H, J
= 2.0 Hz), 4.28 (m, 1H), 4.21 (s, 2H), 3.84 (s, 6H), 3.28 (m, 1H), 3.27 (s, 6H), 2.34 (s, 3H), 2.19 (s,
3H), 2.10-2.08 (m, 4H), 1.85-1.83 (m, 4H).
Example 2612
Ar2-{c/5-4-[(3-Bromobenzyl)amino]cyclohexyI}-A^A4»5,6-tetramethylpyrimidine-2,4-diamine
bis-trifluoroacetate
Step A: Synthesis of V-lC1-5-^KS-bromobenzylJaminolcyclohexylJ-A^^V4^^-
tetramethylpyrimidine-2,4-diamine bis-trifluoroacetate.
Using the procedure of Example 2611, the title compound was obtained as a white solid
TFA salt.
ESI MS m/e 432.4 M+H* ; ]H NMR (400 MHz, CD3OD) 5 7.78 (s, 1H), 7.68 (d, 1H, J= 8.0 Hz),
7.54 (d, 1H, J = 7.6 Hz), 7.45 (t, 1H, J = 4 Hz), 4.29 (m, 3H), 3.28 (m, 1H), 3.27 (s, 6H), 2.34 (s,
3H), 2.20 (s, 3H), 2.11-2.09 (m, 4H), 1.87-1.82 (m, 4H).
Example 2613
Ar-(c/5-4-{[4-(Dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-N'-(3-
methoxyphenyl)urea trifluoroacetate

542
Step A: Synthesis of Ar-(m-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2yl]amino}-
cyclohexyl)-N'-(3-methoxyphenyl)urea trifluoroacetate.
To a solution of cw-4-(4-dimethyIamino-5,6-dimethyl-pyrimidin-2-ylamino)-l-
aminocyclohexane (26.3 mg, 0.1 mmol) in 0.5 mL DMSO was added 3-methoxyphenyl isocyanate
(13.1 uL, 0.1 mmol). The mixture was stirred at room temperature overnight and then 0.5 mL of
DMSO was added to the mixture. The compound was then subject to purification by prep LC MS
to yield 7V-(c/5-4-{[4-(dimethylamino)-5,6-dimethyl pyrimidin-2-yI]amino}cyclohexyl)-N'-(3-
methoxyphenyl)urea trifluoroacetate (28 mg, 0.053 mmol, 53%) as a white solid.
ESI MS m/e 413.6 M+H+ ; !H NMR (400 MHz, CD3OD) 5 7.18 (m, 2H), 6.86 (dd, 1H, /, = 8.0 Hz,
J2 = 2.0 Hz), 6.58 (dd, 1H, Jx - 8.4 Hz, J2 = 2.4 Hz), 4.03 (m, 3H), 3.82 (m, 1H), 3.79 (s, 3H), 3.27
(s, 6H), 2.33 (s, 3H), 2.19 (s, 3H), 1.92-1.73 (m, 8H).
Example 2614
A^(3^-Difluorophenyl)-N'-(ci5-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino}cyclohexyl)urea trifluoroacetate
Step A: Synthesis of Ar-(3^-difluorophenyl)-N'-(cw-4-{[4-(dimethyIamino)-5,6-
dimethylpyriniidin-2-yl]amino}cyC1-5hexyl)urea trifluoroacetate.
Using the procedure of Example 2613, the title compound was obtained as a white solid
TFA salt.
ESI MS m/e 419.3 M+H+ ; 'H NMR (400 MHz, CD3OD) 8 7.08-7.03 (m, 2H), 6.55-6.49 (m, 1H),
4.04 (m, 1H), 3.81 (m, 1H), 3.28 (s, 6H), 2.33 (s, 3H), 2.20 {s, 3H), 1.93-1.73 (m, 8H).
Example 2615

543
l-(4-Chlorophenyl)-Af-(c/s-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclobutanecarboxamide trifluoroacetate
Step A: Synthesis of l-(4-chlorophenyl)-7V-(c«-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclobutanecarboxamide trifluoroacetate.
To a solution of c«-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-l-
aminocyclohexane (35 mg, 0.14 mraol), l-(4-chlorophenyl)-cyclobutanecarboxylic acid (30 mg, 1
eq.) in DC1-5 (2 mL) was added HATU (58 mg, 1.1 eq.) and followed by Et3N (40 uL, 2 eq.)- The
reaction was stirred at room temperature for 4 h, and completion of the reaction was confirmed by
LC1-5S. After removal of the volatile solvent, the residue was purified by prep-HPLC to give 32
mg (41 %) of l-(4-chlorophenyI)-Ar-(c/5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclobutanecarboxamide trifluoroacetate as a white solid.
ESI MS m/e 442 M + H*; ]H NMR (400 MHz, CDC13) 8 13.6 (bs, 1 H), 8.38 (d, \R,J = 7.2 Hz),
7.32-7.22 (m, 5 H), 5.76 (d, 1H,J= 8.8 Hz), 4.09 (bs, 1 H), 3.81 (m, 1 H), 3.26 (s, 6 H), 2.77 (m,
2 H), 2.44 (m, 2 H), 2.22 (s, 3 H), 2.02 (m, 1 H), 1.86 (m, 1 H), 1.65-1.50 (m, 8 H).
Example 2616
2-(4-ChIorophenyl)-A'-(a5-4-{[4-(dimethylamino)-5-inethylpyrimidin-2-yl]amino}cyclohexyl)-
2-methylpropanamide trifluoroacetate
Step A: Synthesis of 2-(4-chlorophenyl)-Ar-(c/s-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-methylpropanamide trifluoroacetate.
Using the procedure of Example 2615, the title compound was obtained.
ESI MS m/e 430 M + H+; ]H NMR (400 MHz, CDC13) 5 13.3 (bs, 1 H), 8.21 (d, 1 H, J= 7.6 Hz),
7.28(bs,4H)57.22(m, 1 H), 5.67 (d, 1 H, /= 8.4 Hz), 4.09 (bs, lH),3.85(m, 1 H), 3.26 (s, 6 H),
2.22 (s, 3 H), 1.71-1.61 (m,6H), 1.54 (s, 6 H), 1.50 (m, 2 H).

544
Example 2617
2-[3,5-bis(Trifluoromethyl)phenyl]-A'-(c«-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yI]amino}cyclohexyI)-2-methylpropanamide trifluoroacetate
Step A: Synthesis of 2-[3^-bis(trifluoromethyl)phenyI]-7V-(C1-5-4-{[4-(dimethylamino)-5-
methylpyrimidin-2~yI]amino}cyclohexyl)-2-methylpropanamide trifluoroacetate.
Using the procedure of Example 2615, the title compound was obtained.
ESIMSm/e532M + H+;'HNMR(400MHz, CDCI3) 5 13.9 (bs, 1 H), 8.68 (d, lH,J = 7.6Hz),
7.78 (s, 2 H), 7.72 (s, 1 H), 7.21 (d, 1 H, J = 4.4 Hz), 6.14 (d, 1 H, J = 8.4 Hz), 4.20 (bs, 1 H), 3.93
(m, 1 H), 3.26 (s, 6 H), 2.22 (s, 3 H), 1.77-1.56 (m, 8 H), 1.61 (s, 6 H).
Example 2618
2-[3,5-bis(Trifluoromethyl)phenyI]-Ar-(c/5-4-{I4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)acetamide trifluoroacetate
Step A: Synthesis of 2-[3^-bis(trifluoromethyl)phenyl]-iV-(cw-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)acetamide trifluoroacetate.
Using the procedure of Example 2615, the title compound was obtained.
ESI MS m/e 504 M + H+; ]HNMR (400 MHz, CDC13) 5 13.8 (bs, 1 H), 8.51 (d, 1 H, J= 7.8 Hz),
7.78 (s, 2 H), 7.73 (s, 1 H), 7.22 (m, 1 H), 5.87 (d, 1 H,J = 8.0 Hz), 4.15 (bs, lH),3.96(m, 1 H),
3.62 (s, 2 H), 3.28 (s, 6 H), 2.24 (s, 3 H), 1.80-1.65 (m, 8 H).
Example 2619
l-(4-Chlorophenyl)-Ar-(c/s-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide trifluoroacetate

545
Step A: Synthesis of l-(4-Chlorophenyl)-7V-(cw-4-{[4-(dimethylaiiiino)-6-methylpyriniidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide trifluoroacetate.
To a solution of cw-4-(4-dimethyIamino-6-methyl-pyrimidin-2-ylamino)-l-
aminocyclohexane (36 mg, 0.14 mmol), l-(4-chlorophenyl)-cyclopropanecarboxylic acid (31 mg, 1
eq.) in DC1-5 (2 mL) was added HATU (60 mg, 1.1 eq.) and followed by Et3N (40 uL, 2 eq.). The
reaction was stirred at room temperature for 4 h, and completion of the reaction was confirmed by
ESI MS. After removal of the volatile solvent, the residue was purified by prep-HPLC to give 45
mg (72 %) of l-(4-Chlorophenyl)-7V-(c/5-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropane carboxamide trifluoroacetate as a white solid.
ESI MS m/e 428 M + H";1 H NMR (400 MHz, CDCi3) 5 13.4 (bs, 1 H), 8.61 (d, 1 H, 7 = 7.2 Hz),
7.32 (m, 4 H), 5.70 (s, 1 H), 5.46 (d, 1 H, J= 8.0 Hz), 4.04 (bs, 1 H), 3.79 (m, 1 H), 3.21 (s, 3 H),
3.10 (s, 3 H), 2.31 (s,3H), 1.68-1.47 (m, 9 H), 1.22 (m, 1 H), 1.00 (m,2H).
Example 2620
l-(4-Chlorophenyl)-Ar-(cw-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclobutanecarboxamide trifluoroacetate
Step A: Synthesis of l-(4-chlorophenyI)-Ar-(C1-5-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclobutanecarboxamide trifluoroacetate.
Using the procedure of Example 2619, the title compound was obtained.
ESI MS m/e 442 M + H+; ]H NMR (400 MHz, CDC13) 5 13.1 (bs, 1 H), 8.41 (d, 1 H, J = 7.6 Hz),
7.28 (s, 4 H), 5.95 (d, I H, J = 8.8 Hz), 5.72 (s, 1 H), 4.14 (bs, 1 H), 3.82 (m, 1 H), 3.21 (s, 3 H),
3.11 (s,3H),2.77(m,2H),2.44(m,2H),2.31(s,3H),2.01(m, 1 H), 1.83 (m, 1 H), 1.70-1.50
(m, 8 H).

546
Example 2621
l-(2,4-DichIorophenyl)-7V-(C1-5-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cydohexyl)cyclopropanecarboxamide trifluoroacetate
Step A: Synthesis of l-(2,4-dichlorophenyl)-Ar-(c/s-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yl)amino}cyclohexyl)cyclopropanecarboxamide trifluoroacetate.
Using the procedure of Example 2619, the title compound was obtained.
ESI MS m/e 462 M + H+; ]H NMR (400 MHz, CDC13) 5 13.4 (bs, 1 H), 8.54 (bs, 1 H), 7.43 (s, 1
H),7.28(d, lH,J=8.4Hz), 7.26(d, 1 H, J= 8.0 Hz), 5.70 (s, 1H), 5.39(d, 1 H, J -8.0 Hz),
4.06 (bs, 1 H), 3.84 (m, 1 H), 3.20 (s, 3 H), 3.10 (s, 3 H), 2.30 (s, 3 H), 1.69-1.62 (m, 8 H), 1.50 (m,
2H), 1.01 (m,2H).
Example 2622
2-[3^-bis(Trifluoromethyl)phenyl]-A'-(c«-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)-2-methylpropanamide trifluoroacetate
Step A: Synthesis of 2-[3,5-bis(trifluoromethyl)phenyl]-iV-(cis-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yl]amino}cyclohexyI)-2-methylpropanamide trifluoroacetate.
Using the procedure of Example 2619, the title compound was obtained.
ESI MS m/e 532 M + H+; 'H NMR (400 MHz, CDC13) 5 13.8 (bs, 1 H), 8.80 (d, 1 H, J = 8.4 Hz),
7.79 (s, 2 H), 7.72 (s, 1 H), 6.20 (d, 1 H, J = 8.4 Hz), 5.70 (s, 1 H), 4.24 (bs, 1 H), 3.94 (bm, 1 H),
3.22 (s, 3 H), 3.10 (s, 3 H), 2.30 (s, 3 H), 1.79-1.60 (m, 8 H), 1.61 (s, 6 H).
Example 2623
2-(3,4-difluorophenyl)-A'-(c/5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)-2-hydroxyacetamide hydrochloride

547
Step A: 2-(3,4-difluorophenyI)-Ar-(c/5-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-hydroxyacetamide hydrochloride.
To a solution of ds-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-l-
aminocyclohexane (43 mg, 0.17 mmol), 3,4-difluoro mandelic acid (34 mg, 1 eq.) in DC1-5 (2 mL)
was added HATU (68 mg, 1.1 eq.) and followed by Et3N (50 jiL, 2 eq.). The reaction was stirred at
room temperature for 4 h and quenched. After removal of the volatile solvent, the residue was
purified by column chromatography (DC1-5 : MeOH = 100 : 0 to 94 : 6). 28 mg (39 %) of the
product was isolated and converted into HC1 salt.
ESI MS m/e 420 M + H+; *H NMR (400 MHz, CDC13) 8 8.48 (d, 1 H, J = 8.0 Hz), 7.39-7.20 (m, 3
H), 7.04 (m, 1H), 5.05 (s, 1 H), 4.08 (bs, 1 H), 3.89 (bs, 1 H), 3.26 (s, 6 H), 2.22 (s, 3 H), 1.78-1.60
(m, 8 H), two exchangeable protons (-NH- and -OH) were not detected.
Example 2624
Ar-(c/$-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-hydroxy-2-[3~
(trifluoromethyl)phenyljacetamide
Step A: Synthesis of A^cw-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyc!ohexyl)-2-hydroxy-2-[3-(trifluoromethyl)phenyl]acetainide.
Using the procedure of Example 2623, the title compound was obtained.
ESI MS m/e 452 M + tT; ]H NMR (400 MHz, CDC13) 6 7.83 (bs, 1 H), 7.22 (s, 1 H), 7.65 (d, 1 H,
J= 8.0 Hz), 7.51 (d, 1 H, J= 8.0 Hz), 7.42 (t, 1 H, J = 8.0 Hz), 7.22 (s, 1 H), 7.00 (d, 1 H, J= 8.0
Hz), 5.10 (s, 1 H), 4.04 (bs, 1 H), 3.89 (bs, 1 H), 3.20 (s, 6 H), 2.18 (s, 3 H), 1.78-1.64 (m, 8 H),
one exchangeable proton (-OH) was not detected.
Example 2625

548
iV-(ci5-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-hydroxy-2-(4-
methoxyphenyl)acetamide
Step A: Synthesis of Ar-(cw-4-{I4-(dimethylamino)-5-methylpyriinidin-2-yl]amino}-
cyclohexyl)-2-hydroxy-2-(4-niethoxyphenyl)acetamide.
Using the procedure of Example 2623, the title compound was obtained.
ESI MS m/e 414 M + H+; *H NMR (400 MHz, CDC13) 5 8.72 (d, 1 H, J= 6.8 Hz), 7.31 (d, 2 H, J=
8.4 Hz), 7.22 (s, 1 H), 6.83 (d, 2 H, J= 8.4 Hz), 6.78 (d, 1 H, J= 7.6 Hz), 4.98 (s, 1 H), 4.06 (bs, 1
H), 3.90 (bs, 1 H), 3.76 (s, 3 H), 3.25 (s, 6 H), 2.20 (s, 3 H), 1.78-1.64 (m, 8 H.
Example 2626
2-(3-Chlorophenyl)-Ar-(c/$-4-{[4-(diiiiethylainino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-
2-hydroxyacetamide
Step A: Synthesis of 2-(3-chlorophenyl)-7V-(m-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-hydroxyacetamide.
Using the procedure of Example 2623, the title compound was obtained.
ESI MS m/e 418 M + H+; *H NMR (400 MHz, CDC13) 5 8.63 (bs, 1 H), 7.44 (s, 1 H), 7.33 (m, 1 H),
7.21 (m, 2 H), 7.12 (bs, 1 H), 5.03 (s, 1 H), 4.08 (bs, 1 H), 3.88 (bs, 1 H), 3.24 (s, 6 H), 2.19 (s, 3
H), 1.78-1.63 (m, 8 H).
Example 2627
2-(23-Difluorophenyl)-Ar-(c/s-4-{|4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-hydroxyacetamide

549
Step A: Synthesis of 2-(2r5-difluorophenyl)-7V-(cw-4-{[4-(dimethylamino)-5-methylpyrimidin-
2-yl]amino}cyclohexyl)-2-hydroxyacetamide.
Using the procedure of Example 2623, the title compound was obtained.
ESI MS m/e 420 M + H+; 'H NMR (400 MHz, CDC13) 5 7.26 (s, 1 H), 7.14 (m, 1H), 7.06 (m, 2 H),
6.73 (d, 1 H, J= 8.0 Hz), 5.32 (s, 1 H), 4.06 (bs, 1 H), 3.93 (bs, 1 H), 3.22 (s, 6 H), 2.20 (s, 3 H),
1.78-1.64 (m, 8 H).
Example 2628
Ar-(cw-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-
(trifluoromethyl)benzenesulfonamide hydrochloride
Step A: Synthesis of iV-(c«-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyC1-5hexyl)-2-(trifluoromethyI)benzenesulfon amide hydrochloride.
To a solution of c/5-4-(4-dimethyIamino-5-methyl-pyrimidin-2-ylamino)-l-
aminocyclohexane (45 mg, 0.18 mmol) in IPA (2 mL) was added 2-trifluoromethyl
benzenesulfonyl chloride (44 mg, 1 eq.) and followed by DIEA (50 (iL, 2 eq.). The reaction was
stirred at room temperature for 1.5 h under an inert atmosphere, and the progress of the reaction
was monitored by ESI MS. The reaction was diluted with DC1-5 (7 mL), washed with saturated
NaHCO3 (1x5 mL) and water (1x5 mL), and concentrated. The crude product was purified by
column chromatography (DC1-5 : MeOH = 100 : 0 to 95 : 5). 31 mg (38 %) of the product was
isolated and converted into HCI salt.
ESI MS m/e 458 M + H+; lH NMR (400 MHz, DMSO-J6) 5 12.2 (bs, 1 H), 8.13 (m, 2 H), 8.06 (d,
1 H, J = 6.0 Hz), 7.93 (d, 1 H, J= 8.0 Hz), 7.87 (t, 1 H, J= 7.6 Hz), 7.79 (t, 1 H, J= 7.6 Hz), 7.62
(bs, 1 H), 3.78 (bs, 1 H), 3.22 (s, 6 H), 3.21 (bs, 1 H), 2.20 (s, 3 H), 1.78-1.54 (m, 8 H).
Example 2629

550
4-Chloro-Ar-(c«-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-
benzenesulfonamide hydrochloride
Step A: Synthesis of 4-chloro-Ar-(m-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzenesulfonamide hydrochloride.
Using the procedure of Example 2628, the title compound was obtained.
ESI MS m/e 424 M + H+; 'H NMR (400 MHz, DMSO-J6) 5 11.9 (bs, 1 H), 7.92 (bs, 1 H), 7.83 (s,
I H, overlapped with the doublet of 7.81 ppm), 7.81 (d, 2 H, J= 8.4 Hz), 7.64 (d, 2 H, J= 8.4 Hz),
7.58 (bs, 1 H), 3.74 (bs, 1 H), 3.21 (s, 6 H), 3.08 (bs, 1 H), 2.20 (s, 3 H), 1.70-1.44 (m, 8 H).
Example 2630
2-Bromo-Ar-(c«-4-{I4-(dimethylamino)-5-inethylpyrimidin-2-yl]amino}cyclohexyl)-
benzenesulfonamide hydrochloride
Step A: Synthesis of 2-bromo-Ar-(ds-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
y 1]aminojcyclohexyl)benzenesulfonamide hydrochloride.
Using the procedure of Example 2628, the title compound was obtained.
ESI MS m/e 468 M + H+; ]H NMR (400 MHz, DMSO-tf6) 5 11.9 (bs, 1 H), 8.00 (d, 1 H, J= 7.2
Hz), 7.92 (bs, 1 H), 7.82 (d, 2 H, J= 7.6 Hz), 7.59-7.48 (m, 3 H), 3.73 (bs, 1 H), 3.21 (s, 6 H), 3.20
(bs, 1 H), 2.20 (s, 3 H), 1.72 (m, 2 H), 1.58 (m, 6 H).
Example 2631
Ar-(c«-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)thiophene-2-
sulfonamide hydrochloride

551
Step A: Synthesis of ^-(^-^{[^(dimethylaminoJ-S-methylpyrimidin-l-ylJamino}-
cyC1-5hexyI)thiophene-2-suIfonamide hydrochloride.
Using the procedure of Example 2628, the title compound was obtained.
ESI MS m/e 396 M + H+; lH NMR (400 MHz, DMSO-rf6) 5 12.1 (bs, 1 H), 7.99 (bs, 1 H), 7.92 (bs,
1 H), 7.88 (d, 1 H, J= 4.8 Hz), 7.60 (bs, 1 H), 7.57 (d, 1 H, J= 2.8 Hz), 7.14 (t, 1 H, J= 4.8 Hz),
3.75 (bs, 1 H),3.22(s, 6H),3.17(bs, 1 H), 2.20 (s, 3 H), 1.70-1.51 (m, 8 H).
Example 2632
A^jA^jS-Trimethyl-A^^cry-^IP-ttrifluoromethy^benzylJaminolcyclohexy^pyrimidine^^-
diamine bistrifluoroacetate
Step A: Synthesis of iV^/V^S-tri methyl- 7V2-(c/s-4-{[3-(trifluoromethyl)benzyllamino}-
cyclohexyl)pyrimidine-2,4-diamine bistrifluoroacetate.
A solution of cw-4-(4-dimethylamino-5-methyl-pyrimidin-2-yIamino)-l-
aminocyclohexane (31 mg, 0.12 mmol) and 3-trifluoromethyl benzaldehyde (22 mg, 1 eq.) in
MeOH (1.5 mL) was stirred at room temperature for 4 h. NaBH(OAc)3 (85 mg, ~ 4 eq.) was added
into the reaction, and the reaction was stirred overnight. The reaction was quenched with water,
extracted with DC1-5, concentrated, and purified by prep-HPLC. 35 mg (54 %) of N*,N*,5-
trimethyI-Ar2-(c/5-4-{[3-(trifluoromethyl)benzyI]amino} cyclohexyI)pyrimidine-2,4-diamine
bistrifluoroacetate was isolated as a white powder.
ESI MS m/e 408 M + H+; !H NMR (400 MHz, CDCI3) 5 13.7 (bs, 1 H), 9.70 (bs, 2 H), 8.60 (d, 1 H,
J= 8.8 Hz), 7.70 (m, 2 H), 7.59 (d, 1 H, J= 8.0 Hz), 7.48 (t, 1 H, J= 8.4 Hz), 4.31 (m, 1 H), 4.23
(s, 2 H), 3.30 (m, 1 H), 3.29 (s, 6 H), 2.25 (s, 3 H), 2.05 (m, 2 H), 1.93 (m, 4 H), 1.64 (m, 2 H).
Example 2633
iV2-(ciy-4-{[4-(Difluoromethoxy)benzyl]amino}cyclohexyl)-V^V4,5-trimethylpyrimidine-2,4-

552
diamine bistrifluoroacetate
Step A: Synthesis of A^2-(cK-4-{[4-(difluoromethoxy)benzyI]amino}cyclohexyI)-A'4,A'4,5-
trimethylpyrimidine-2,4-diamine bistrifluoroacetate.
Using the procedure of Example 2632, the title compound was obtained.
ESI MS m/e 406 M + H+; lH NMR (400 MHz, CDC13) 5 13.8 (bs, 1 H), 9.60 (bs, 1 H), 8.60 (d, 1 H,
J= 8.8 Hz), 7.46 (d, 2 H, J= 8.8 Hz), 7.24 (s, 1 H), 7.07 ( d, 2 H, J= 8.8 Hz), 6.48 (t, 1 H, JF.H =
73.6 Hz), 4.31 (m, 1 H), 4.15 (s, 2 H), 3.40 (bs, 1 H), 3.29 (s, 6 H), 2.24 (s, 3 H), 2.05 (m, 2 H),
1.90 (m, 4 H), 1.63 (m, 2 H).
Example 2634
Ar-{c/5-4-[(3-Bromo-4-methoxybenzyl)amino]cyclohexyl}-A4^V4,5-trimethylpyrimidine-2,4-
diamine bistrifluoroacetate
Step A: Synthesis of Ar2-{c/$-4-[(3-bromo-4-methoxybenzyl)amino]cyC1-5hexyl}-Ar*^V4,5-
trimethylpyrimidine-2,4-diamine bistrifluoroacetate.
Using the procedure of Example 2632, the title compound was obtained.
ESI MS m/e 448 M + H4"; 'H NMR (400 MHz, CDC13) 5 13.8 (bs, 1 H), 9.44 (bs, 1 H), 8.57 (d, 1 H,
J= 8.0 Hz), 7.58 (d, 1 H, J= 2.4 Hz), 7.41 (dd, 1 H, J= 8.8 and 2.0 Hz), 7.24 (s, 1 H), 6.86 ( d, 1 H,
J= 8.0 Hz), 4.29 (m, 1 H), 4.07 (s, 2 H), 3.86 (s, 3 H), 3.28 (s, 6 H), 3.25 (bs, 1 H), 2.24 (s, 3 H),
2.05-1.85 (m, 6 H), 1.64 (m, 2 H).
Example 2635
7V2-(3,4-Dichlorophenyl)-7V-(c75-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-/V2-methylglycinamide bistrifluoroacetate

553
Step A: Synthesis of 2-bromo-Af-[4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexyl]-acetamide.
czj-[4-(4-dimethylamino-5-methyl-pyrimidm-2-ylamino) cyclohexyl]-carbamic acid tert-
butyl ester (3.5 g, 14.0 mmol) was dissolved in 20 mL of methylene chloride, and cooled to 0°C in
an ice bath. Bromo-acetyl bromide (1.26 mL, 14.0 mmol) was added dropwise into the stirring
solution over the ice bath. The reaction mixture was stirred at room temperature for 10 minutes.
Methylene chloride was evaporated off to yield 2-bromo-JV-[4-(4-dimethylarnino-5-methyl-
pyrimidin-2-yIamino)-cyclohexyI]-acetamide as a pinkish crude solid. (6.1g, 95%).
ESI MS m/z 370.1 (M + ¥t) ; *HNMR(400 MHz, CDC13) 5 12.20 (s, 1H), 8.21 (d, 7= 7.2 Hz,
1H), 6.85 (d, J= 6.8 Hz, 1H), 4.15 (s, 1H), 3.97-3.89 (m, 3H), 3.31 (s, 6H), 2.27 (s, 3H), 1.93-1.72
(m, 8H).
Step B: Synthesis of Ar2-(3,4-dichlorophenyI)-Ar-(cw-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)-7V-inethyIglycinamide bistrifluoroacetate.
2-Bromo-A/-[4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyC1-5hexyl]-acetamide
(50 mg, 0.135 mmol) and (3,4-dichioro-phenyl)-methyl-amine (48 mg, 0.270 mmol) were
dissolved in 0.8 mL of DMF. The reaction mixture was heated via Smith Synthesizer at 180°C for
50 minutes. The crude was purified by HPLC to give A^2-(3,4-dichlorophenyl)-Ar-(c/5-4-{[4-
(dimethylamino^S-methylpyrimidin^-y^aminoJcyclohexy^-A^-methylglycinamide
bistrifluoroacetate as a white solid. (12.8 mg, 18%)
ESI MS m/z 465.3 (M + H*) ; !H NMR (400 MHz, CDC13) 6 8.75 (d, J= 6.0 Hz, 1H), 6.80 (d, J =
2.8 Hz, 1H), 6.67-6.65 (m, 1H), 6.57 (dd, J= 9.0, 3.0 Hz, 1H), 4.13 (s, 1H), 3.98 (s, 1H), 3.86 (s,
2H), 3.29 (s, 6H), 3.06 (s, 3H), 2.25 (s, 3H), 1.73-1.62 (m, 8H).
Example 2636
Ar-[((lJ?r31y)-3-{[4-(Dimethylaniino)-5-niethylpyrimidin-2-yI]ainino}cyclopeiityl)methyl]-2-(4-
fluorophenoxy)nicotinamide trifluoroacetate

554
Step A: Synthesis of (3-{[(2-Chloro-pyridine-3-carbonyI)-amino]-methyl}-cyclopentyl)-
carbamic acid tert-butyl ester.
(3-Aminomethyl-cyclopentyl)-carbamic acid tert-butyl ester (0.050 g, 0.23 mmol), 2-
chloronicotinoyl chloride (0.041 g, 0.23 mmol), and diisopropylethylamine (0.061 mL, 0.34 mmol)
were combined in dichloromethane (2.00 mL) at ambient temperature and stirred 18 hrs. The
mixture was concentrated and purified by flash silica chromatography (5% methanol in ethyl
acetate) to give (3-{[(2-chloro-pyridine-3-carbonyl)-amino]-methyl}-cyclopentyl)-carbamic acid
tert-butyl ester (0.035 g, 43%) as a solid.
ESI MS m/e 354, M + H+; 'H NMR (400 MHz, CDC13) 5 8.47 (dd, Jaa = 1.5 Hz, Jab = 4.7 Hz, 1
H), 8.11 (dd, Jaa = 1.5 Hz, Jab = 7.6 Hz, 1 H), 7.35 (dq, Jaa = 1.2 Hz, Jab = 4.8 Hz, Jac = 7.6 Hz,
1 H), 6.56 (bs, 1 H), 4.59 (bs, 1 H), 3.97 (m, 1 H), 3.48 (m, 2 H), 2.27 (m, 2 H), 1.94 (m, 2 H), 1.49
(m, 1 H), 1.44 (s, 9 H), 1.25 (m, 2 H).
Step B: Synthesis of AL(3-Amino-cyclopentylmethyl)-2-(4-fluoro-phenoxy)-nicotinamide.
(3-{[(2-Chloro-pyridine-3-carbonyI)-amino]-methyl}-cyclopentyl)-carbamic acid tert-butyl
ester (0.23 mmol), 4-fluorophenoI (0.026 g, 0.23 mmol), cesium carbonate (0.152 g, 0.46 mmol),
and dioxane (2.00 mL) were combined and heated to 180°C for 1 hr. utilizing a SmithSynthesizer
microwave apparatus. Trifluoroacetic acid (3.00 mL) was added and the mixture stirred 18 hrs.
Then it was concentrated, neutralized with saturated aqueous NaHCO3, extracted with
dichloromethane, and concentrated to giveJV-(3-amino-cyclopentylmethyl)-2-(4-fluoro-phenoxy)-
nicotinamide as the crude product.
ESI MS m/e 330, M + H"; lH NMR (400 MHz, CDC13) 5 8.52 (dd, Jaa = 1.0 Hz, Jab = 7.6 Hz, 1 H),
8.19 (dd, Jaa = 1.9 Hz, Jab = 3.9 Hz, I H), 8.06 (t, J= 5.8 Hz, 1 Hz), 6.91 (t, J= 8.2 Hz, 1 H), 6.77
(dd, Jaa = 3.6 Hz, Jab = 3.2 Hz, I H), 3.62 (m, 2 H), 2.26 (m, 2 H), 2.05 (m, 1 H), 1.81 (m, 2 H),
1.62 (m, 1H), 1.48 (m, 2 H).
Step C: Synthesis of Ar-[((l^^1S)-3-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]-

555
uminoj cyclopentyl) methyl]-2-(4-fluorophenoxy)nicotinamide trifiuoroacetate.
5-Methyl-4-dimethylamino-2-chloropyrimidine (0.040 g, 0.23 mmol), iV-(3-amino-
cyclopentylmethyl)-2-(4-fluoro-phenoxy)-nicotinamide (0.23 mmol), diisopropyl-ethylamine
(0.061 mL, 0.34 mmol), and isopropanol (2.00 mL) were combined and heated to 180°C for 2 hrs.
utilizing a SmithSynthesizer microwave apparatus. The mixture was then purified by prep LC1-5S
(gradient: 15-95% acetonitrile-water with 0.05% TFA) to give iV-[((lJ?,3S)-3-{[4-(dimethylamino)-
5-methyIpyrimidin-2-yl]amino} cyclopentyl) methyl]-2-(4-fluorophenbxy)nicotinamide
trifluoroacetate as a white solid (0.018 g, 13.5% over two steps).
ESI MS m/e 465, M + HVH NMR (400 MHz, DMSO-d6) 6 11.63 (bs, 1 H), 8.44 (t, 7= 5.7 Hz, 1
H), 8.16 (dd, Jaa = 1.9 Hz, Jab = 4.8 Hz, 1 H), 8.04 (dd, Jaa = 1.8 Hz, Jab = 7.4 Hz, 1 H), 7.98 (bs,
1 H), 7.53 (s, 1 H), 7.25-7.19 (m, 2 H), 4.08 (bs, 1 H), 3.22 (s, 6 H), 2.53 (s, 3 H), 2.19 (m, 2 H),
1.95 (m, 1 H), 1.71 (m, 1 H), 1.54 (m, 2 H), 1.46 (m, 2 H), 1.22 (m, 2 H).
Example 2637
Ar-[((l^,3iy)-3-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclopentyl)methyl]-6-(2-
methoxyphenoxy)nicotinamide trifluoroacetate
Step A: Synthesis of (3-{[(6-Chloro-pyridine-3-carbonyl)-amino]-methyI}-cyclopentyl)-
carbamic acid tert-butyl ester.
(3-Aminomethyl-cyclopentyl)-carbamic acid tert-butyl ester (0.050 g, 0.23 mmol), 6-
chloronicotinoyl chloride (0.041 g, 0.23 mmol), and diisopropylethylamine (0.061 mL, 0.34 mmol)
were combined in dichloromethane (2.00 mL) at ambient temperature and stirred 18 hrs. The
mixture was concentrated and purified by flash silica chromatography (5% methanol in ethyl
acetate) to give an orange gel.
ESI MS m/e 354, M + H+; ]H NMR (400 MHz, CDC13) 5 8.75 (d, J = 2.1 Hz, 1 H), 8.09 (dd, Jaa =
1.8 Hz, Jab = 8.3 Hz, 1 H), 7.41 (d, J= 8.3 Hz, 1 H), 6.48 (bs, 1 H), 4.65 (d, J= 8 Hz, 1 H), 3.92

556
(m, 1 H), 3.46 (m, 2 H), 2.25 (m, 2 H), 1.98 (m, 2 H), 1.81 (ra, 1 H), 1.47 (s, 9 H), 1.18 (m, 2 H).
Step B: Synthesis of A^-[((li?,35)-3-{[4-(dimethylamino)-5-methyIpyriniidin-2-
yl]amino}cyclopentyl)methyl]-6-(2-methoxyphenoxy)nicotinamide trifluoroacetate.
(3-{[(6-Chloro-pyridine-3-carbonyl)-amino]-methyl}-cyclopentyl)-carbamic acid tert-butyl
ester (0.23 mmol), 2-methoxyphenol (0.029 g, 0.23 mmol), cesium carbonate (0.152 g, 0.46 mmol),
and dioxane (2.00 mL) were combined and heated to 180°C for 1 hr. utilizing a Smith Synthesizer
microwave apparatus. Trifluoroacetic acid (3.00 mL) was added and the mixture stirred 18 hrs.
Then it was concentrated, neutralized with saturated aqueous NaHCO3, extracted with
dichloromethane, and concentrated to give a foam. 5-Methyl-4-dirnethylarnino-2-chloropyrimidine
(0.040 g, 0.23 mmol), diisopropylethylamine (0.061 mL, 0.34 mmol), and isopropanol (2.00 mL)
were added and the combined mixture was heated to 180 °C for 2 hrs utilizing a Smith synthesizer
microwave apparatus. The mixture was then purified by prep-LC1-5S (gradient: 15-95%
acetonitrile-water with 0.05% TFA) to give A^-[((l^,35)-3-{[4-(dimethylamino)-5-
methyIpyrimidin-2-yI]amino} cyclopenryl)methyl]-6-(2-methoxyphenoxy)nicotinamide
trifluoroacetate as a white solid (0.011 g, 8.1% over four steps).
ESI MS m/e 477, M + H*;1 H NMR (400 MHz, DMSO-d6) 5 9.05 (bs, 1 H), 8.63 (s, 1 H), 8.16 (dd,
Jaa - 2.2 Hz, Jab = 8.6 Hz, 1 H), 7.58 (bs, 1 H), 7.23 (s, 1 H), 7.19 (d, J = 6.2 Hz, 1 H), 7.16 (dd,
Jaa = 1.5 Hz, Jab = 7.7 Hz, 1 H), 7.00 (t, J= 8.8 Hz, 1 H), 6.91 (d, J= 12 Hz, 1 H), 4.25 (bs, 1 H),
3.75 (s, 3 H), 3.66 (m, 1 H), 3.29 (s, 6 H), 3.11 (m, 2 H), 2.52 (m, 2 H), 2.23 (s, 3 H), 2.10 (m, 2 H),
1.78 (m, 1H), 1.62 (m, 2 H).
Example 2638
Ar-(c/$-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-2-(3-
fluorophenoxy)acetamide
Step A: Synthesis of Ar-[c«-4-(4-dimethyIamino-5-methyl-pyrimidin-2-ylamino)-cyelohexyl]-

557
bromoacetamide.
To a solution of cw-4-(4-dimethylamino-5-methyl-pyrimidin-2-yIamino)-l-
aminocyclohexane (150 mg, 0.6 mmol) in DC1-5 (10 mL) was added dropwise bromacetylbromide
(120 mg, 1 eq.) at 0 °C under an inert atmosphere. After 5 min stirring, DIEA (0.1 mL, 1 eq.) was
added into the reaction. The reaction was stirred for an additional 3 h at below 15 °C, quenched,
and purified by column chromatography.
0.12 g (55 %) of the product was isolated.
Step B: Synthesis of A^c/s-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}-
cyclohexyl)-2-(3-fluorophenoxy)acetamide.
A sealed tube containing a heterogenous solution of N-[c/s-4-(4-dimethylamino-5-methyl-
pyrimidin-2-ylaraino)-cyC1-5hexyl]-bromoacetamide (30 mg, 0.08 mmol), 3-fluorophenol (27 mg, 3
eq.), and Cs3CO3 (30 mg, 1.1 eq.) in dioxane (-0.7 mL) was reacted in a Smith microwave
synthesizer for 3000 sec at 180 °C. The reaction was diluted with DC1-5, washed with sat-
NaHCO3 (2 x) and water (1 x), concentrated, and purified by column chromatography to give 11
mg (34 %) of the product.
ESI MS m/e 402 M + HT; 'H NMR (400 MHz, CDC13) 5 7.58 (s, 1 H), 7.26 (m, 1 H), 6.74-6.63 (m,
3H),6.51(d, 1H, .7=8.0 Hz), 5.15 (bs, 1 H), 4.45 (s, 2 H), 4.01 (m, 1 H),3.97(bs, lH),3.05(s,6
H), 2.15 (s, 3 H), 1.82-1.61 (m, 8 H).
Example 2639
2-[(5-Ch]oropyridin-3-yl)oxyI-7V-(C1-5-4-{l4-(dimethyiamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)acetamide
Step A: Synthesis of 2-[(5-chIoropyridin-3-yl)oxy]-Ar-(C1-5-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyI)acetamide.
Using the procedure of Example 2638, the title compound was obtained.

558
ESI MS m/e 419 M + H+; 'H NMR (400 MHz, CDCI3) 5 8.25 (m, 2 H), 7.53 (s, 1 H), 7.27 (t, 1 H, J
= 2.4 Hz), 6.56 (d, 1 H, J= 7.6 Hz), 5.57 (bs, 1 H), 4.50 (s, 2 H), 4.01 (bs, 2 H), 3.08 (s, 6 H), 2.16
(s,3H), 1.83-1.64 (m, 8 H).
Example 2640
jV-(c/s-4-{[4-(Dimethylamino)-5-ethyIpyrimidin-2-yI]amino}cyclohexyl)-3,4-
difluorobenzamide
Step A: Synthesis of 2,4-dichloro-5-ethylpyrimidine.
To a suspension of 5-ethyluracil (1 g, 7.1 mmol) in POC13 (4.5 mL) was slowly added N,N-
dimethylaniline (1 mL). The reaction was heated at reflux (-120 °C) for 5 h until the starting
material was completely dissolved and the entire solution turned a purple color. The mixture was
allowed to cool and poured very slowly into ice (~40 g). The resulting ppt was filtered and washed
with ice water. The ppt was dissolved with a minimal amount of DC1-5 and poured onto a short
column of silica gel, and the product (1.2 g, ~ 100 %) was obtained by column chromatography
with DC1-5.
'H NMR (400 MHz, CDC13) 5 8.42 (s, 1 H), 2.75 (q, 2H,J= 7.6 Hz), 1.29 (t, 3 H, J= 7.6 Hz).
Step B: Synthesis of A^(c«-4-{[4-(dimethylamino)-5-ethylpyrimidin-2-yl]amino}cyclohexyl)-
3,4-difluorobenzamide.
A solution of 2,4-dichloro-5-ethylpyrimidine (1.2 g, 6.8 mmol), in THF (15 mL) was
cooled to 5 °C in an ice bath, and 2M-dimethylamine (7 mL, 2 eq.) was slowly added. The reaction
was stirred for 2 h at around 10 °C, and the volatile solvent was removed. The residue was purified
by column chromatography (hexane:DC1-5 = 50:50 to 10:90) to give 0.89 g (70 %) of 2-chloro-4-
dimethylamino-5-ethylpyrimidine: ESI MS m/e = 186 M + H+.
A sealed tube containing 2-chloro-4-dimethylamino-5-ethy!pyrimidine (35 mg, 0.019
mmol), c/5-(4-amino-cyclohexyl)-3,4-difluoro-benzamide (48 mg, 1 eq.), DIEA (50 mg, 2 eq.), and

559
IPA (1 mL) was reacted in a Smith microwave synthesizer for 2 h at 180 °C. The reaction was
diluted with DC1-5, washed with 1-N HC1 and water, concentrated, and purified from column
chromatography (DC1-5:MeOH = 100:0 to 95:5) to give 11 mg (14 %) of the product.
ESI MS m/e 404 M + H+; !H NMR (400 MHz, CDC13) 5 7.68 (s, 1 H), 7.61 (m, 1 H), 7.48 (m, 1 H),
7.19 (m, 1H), 5.99 (d, 1 H, J= 12 Hz), 4.38 (d, 1 H, «/= 6.0 Hz), 4.20 (m, lH),4.12(m, 1 H),
3.10 (s, 6 H), 2.29 (q, 2 H, .7=7.2 Hz), 1.96-1.64 (m, 8 H), 1.18 (t, 3 H, J= 7.6 Hz).
Example 2641
A'-[c«-4-({4-[Ethyl(methyl)amino]-5-methylpyrimidin-2-yl}amino)cyclohexyl]-3,4-
difluorobenzamide hydrochloride
Step A: Synthesis of Ar-[c/sp-4-({4-[ethyl(methyl)amino]-5-methylpyrimidin-2-
yl}amino)cyclohexyl]-3,4-difluorobenzamide hydrochloride.
A solution of 2,4-dichloro-5-methylpyrimidine (2.6 g, 16 mmol) and ethyl methylamine
(2.7 mL, 2 eq.) in THF (20 mL) was stirred at the residue was purified by column chromatography. 1.3 g (45 %) of 2-chloro-4-(ethyl-methyl-
amino)-5-methylpyrimidine was isolated.
ESI MS m/e 186M + H+.
A sealed tube containing 2-chloro-4-(ethyl-methyl-amino)-5-methylpyrimidine (80 mg,
0.019 mmol), cw-(4-amino-cyc!ohexyl)-3,4-difluoro-benzamide (100 mg, 1 eq.), DIEA (0.14 mL, 2
eq.), and IPA (1 mL) was reacted in a Smith microwave synthesizer for 2 h at 180 °C. The reaction
was diluted with DC1-5, washed with 1-N HC1 and water, concentrated, and purified by column
chromatography (DC1-5:MeOH = 100:0 to 95:5) to give 35 mg (20 %) of the product, which was
converted to HC1 salt.
ESI MS m/e 404 M + H4"; !H NMR (400 MHz, DMSO-^) 5 12.0 (bs, 1 H), 8.36 (bs, 1 H), 7.97 (d,
1 H,J=6.0Hz), 7.90 (m, 1 H), 7.73 (m, 1 H), 7.63 (s, 1 H), 7.51 (m, 1 H), 3.85 (bm, 2 H), 3.65 (q,
2 H, J= 7.2 Hz), 3.25 (s, 3 H), 2.22 (s, 3 H), 1.84 (m, 2 H), 1.69 (m, 6 H), 1.18 (t, 3 H, J= 7.2 Hz).

560
Example 2642
A/-(c«-4-{[4-(Dimethylamino)-5-(trifluoromethyl)pyrimidiii-2-yl]amino}cyclohexyl)-3,5-
bis(trifluoromethyl)benzamide trifluoroacetate
Step A: Synthesis of 2-chloro-4-dimethylamino-5-trifluoromethylpyrimidine.
To a solution of 2,4-dichloro-5-trifluoromethylpyrimidine (1 g, 4.6 mmol) in THF (15 mL)
was added 2M-dimethylamine (4.6 mL, 2 eq.) at 0 °C. The reaction was stirred for an additional
1.5 h at 90:10:0 to 95:0:5). 0.49 g (47 %) of 2-chIoro-4-dimethylamino-5-trifluoromethylpyrimidine was
isolated.
ESI MS m/e 226 M + ¥t; 'HNMR (400 MHz, CDC13) 6 8.36 (s, 1 H), 3.21 (s, 6 H).
Step B: Synthesis of c/.s-[4-(4-Dimethylamino-5-trifluoromethyl-pyrimidin-2-ylamino)-
cyclohexylj-carbamic acid tert-butyl ester.
A sealed tube containing 2-chloro-4-dimethylamino-5-trifluoromethylpyrimidine (0.49 g,
2.0 mmol), c/s-(4-amino-cyclohexyI)-carbamic acid tert-butyl ester (0.47 g, 1 eq.), DIEA (0.7 mL,
2 eq.) in IPA (2.5 mL) was reacted in a Smith microwave synthesizer for 2 h at 175 °C. The
solution was concentrated and purified by column chromatography (DC1-5:MeOH = 100:0 to 96:4).
0.57 g (65 %) of c/j-[4-(4-dimethylamino-5-trifluoromethyl-pyrimidin-2-yIamino)-cyclohexyl]-
carbamic acid tert-butyl ester was isolated.
ESI MS m/e 404 M + IT; 'HNMR (400MHz, CDC13) 5 8.15 (s, 1 H), 5.10 (bs, 1 H), 4.53 (bs, 1
H), 3.94 (bs, 1 H), 3.61 (bs, 1 H), 3.09 (s, 6 H), 1.78-1.49 (m, 8 H), 1.44 (s, 9 H).
Step C: Synthesis of cw-Ar-(4-dimethy lam in o-5-trifluorom ethyl-py rim idin-2-yl)-cyclo hexane-
1,4-diamine.
To a solution of cw-[4-(4-dimethylamino-5-trifluoromethyl-pyrimidin-2-ylamino)-

561
cyclohexyij-carbamic acid tert-butyl ester (0.55g, 1.3 mmol) in DC1-5 (10 mL) was added TFA (7
mL). The reaction was stirred at room temperature for 2 h and concentrated. The residue was
neutralized with sat-NaOH, and the aqueous layer was extracted with DC1-5 (3 x). The combined
organic layers were washed with water, dried, and concentrated to give 0.25 g (65 %) of cis-N-(4-
dimethylamino-5-trifluoromethyl-pyrimidin-2-yl)-cyC1-5hexane-l,4-diamine.
ESI MS m/e 304 M + H+; *H NMR (400 MHz, CDC13) 5 8.16 (s, 1 H), 5.42 (bs, 1 H), 3.98 (bs, 1
H), 3.09 (s, 6 H), 2.87 (bs, 1 H), 1.81 (m, 2 H), 1.73-1.65 (m, 4 H), 1.43 (m, 4 H).
Step D: Synthesis of 7V-(cw-4-{[4-(dimethyIamino)-5-(trifluoromethyl)pyrimidin-2-
yl]amino}cyclohexyl)-3,5-bis(trifluoromethyl)benzaniide trifluoroacetate.
To a solution of C(5-Ar-(4-dimethylamino-5-trifluoromethyl-pyrimidin-2-yI)-cyclohexane-
1,4-diamine (30 mg, 0.01 mmol) in dry benzene (2 mL) was added 3,5-bistrifluoromethyl benzoyl
chloride (27 mg, 1 eq.) and followed by Et3N (20 j^L, 2.5 eq). The reaction was stirred overnight,
concentrated, and purified by prep-HPLC. 32 mg (49 %) of N-(cis-4-{[4-(dimethy\am'mo)-5-
(trifluoromethyl)pyrimidin-2-yI]amino} cyclohexyl)-3,5-bis(trifluoromethyl)benzamide
trifluoroacetate was isolated as a white powder.
ESI MS m/e 544 M + tT; lH NMR (400 MHz, CDC13) 6 9.35 (d, 1 H, J= 8.0 Hz), 8.47 (s, 1 H),
8.32 (s, 2 H), 8.07 (s, 1 H), 7.61 (d, 1 H, J= 8.4 Hz), 4.31(bs, 1 H), 4.20 (bs, 1 H), 3.33 (s, 6 H),
1.93-1.79 (m, 8 H.
Example 2643
Ar-(c/5-4-{[4-(Dimethylamino)-5-(trifluoromethyl)pyrimidin-2-yIJamino}cyclohexyl)-4-
(trifluoromethoxy)benzamide trifluoroacetate
Step A: Synthesis of Ar-(c/y-4-{[4-(dimethylamino)-5-(trifluoromethyI)pyrimidin-2-
yl]amino}cyclohexyl)-4-{trifluoromethoxy)benzamide trifluoroacetate.
Using the procedure of Example 2642, the title compound was obtained.

562
ESI MS m/e 492 M + H+; lR NMR (400 MHz, CDC13) 8 9.45 (d, 1 H, J= 8.0 Hz), 8.05 (s, 1 H),
7.88 (d, 2H,;= 8.8 Hz), 7.24 (m, 2 H, overlapped with solvent), 7.04 (d, 1 H, J= 8.4 Hz), 4.27 (bs,
1 H), 4.18 (bs, 1 H), 3.31 (s, 6 H), 1.89-1.77 (m, 8 H).
Example 2644
JV-(ciV4-{[4-(DimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-{[3-
(trifluoroniethyl)phenyl]siilfinyl}acetamide hydrochloride
Step A: Synthesis of (3-trifluoromethyI-phenylsulfanyl)-acetic acid ethyl ester.
A solution of ethyl bromoacetate (0.65g, 3.2 mmol), 3-trifluoromethyl thiophenol (0.88 g,
1.5 eq.), and Et3N (1.5 mL) in THF (15 mL) was stirred for 2 h at 62 °C. The mixture was diluted
with DC1-5, washed with sat.-NaHCO3 (3x) and water, dried with MgSO4, and concentrated. The
crude product (0.73 g, 85 %) was used to next reaction without a further purification.
5H NMR (400 MHz, CDC13) 5 7.62 (s, I H), 7.55 (d, 1 H, J = 8.0 Hz), 7.46-7.37 (m, 2 H), 4.16 (q,
2H,/= 7.2 Hz), 3.66 (s, 2 H), 1.22 (t, 3 H, J= 12 Hz).
Step B: Synthesis of (3-trifluoromethyl-phenylsulfinyl)-acetic acid ethyl ester.
To a solution of (3-trifluoromethyl-phenylsulfanyl)-acetic acid ethyl ester (0.5 g, 1.9
mmol) in DC1-5 (10 mL) was added 77 %-MCPBA (0.42 g, 1 eq.) under Ar atmosphere at 0 °C.
The reaction was stirred for an additional 3 fv, diluted with DC1-5, washed with sat-NaHCO3 and
water, and concentrated. (3-trifluoromethyl-phenyIsulfinyl)-acetic acid ethyi ester (0.34 g, 64 %)
and (3-trifluoromethyl-phenylsulfonyl)-acetic acid ethyl ester (0.15 g, 27 %) were isolated by
column chromatography (hexane:EtOAc = 95:5 to 80:20).
(3-Trifluoromethyl-phenyIsulfinyl)-acetic acid ethyl ester:
'H NMR (400 MHz, CDCl3) 5 7.95 (s, 1 H), 7.87 (d, 1 H, J= 8.0 Hz), 7.78 (d, 1 H, J = 8.0 Hz),
7.67 (t, 1 H,/=8.0 Hz), 4.15(q,2H, 7=7.2 Hz),3.86(d, 1 H,J= 14.0 Hz), 3.70 (d, 1 R,J= 14.0
Hz), 1.22 (t, 3 H, .7=7.2 Hz).

563
(3-Trifluoromethyl-phenylsulfonyl)-acetic acid ethyl ester:
'H NMR (400 MHz, CDCI3) 6 8.20 (s, 1 H), 8.14 (d, 1 H, J= 7.6 Hz), 7.94 (d, 1 H, J= 7.6 Hz),
7.74 (t, 1 H, J= 7.6 Hz), 4.15 (s, 2 H), 4.14 (q, 2 H, J= 7.6 Hz), 1.20 (t, 3 H, J= 7.2 Hz).
Step C: Synthesis of (3-trifluoromethyl-phenylsulfinyl)-acetic acid.
To a heterogenous solution of (3-trifluoromethyl-phenyIsulfinyI)-acetic acid ethyl ester
(0.2 g, 0.7 mmol) in H2O (5 mL)/EtOH (0.5 mL) was added KOH (120 mg, 3 eq.). The reaction
was stirred for 2 h at 85 °C, concentrated to about half of the reaction volume, and acidified with
conc-HCl at an ice bath. (3-Trifiuoromethyl-phenyIsuIfinyl)-acetic acid (100 mg, 56 %) was
filtered and dried.
]H NMR (400 MHz, DMSO-t/5) 5 8.05 (s, 1 H), 8.01 (d, 1 H, J= 8.0 Hz), 7.92 (d, 1 H, J = 8.0 Hz),
7.81 (t, 1 H, J = 8.0 Hz), 4.16 (d, 1 H, J= 14.4 Hz), 3.87 (d, 1 H, J= 14.4 Hz).
Step D: Synthesis of A^(cw-4-{[4-(dimethylainino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyI)-2-{[3-(trif1uoromethyl)phenyI]suIfinyI}acetamide hydrochloride.
To a solution of c/5-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-l-
amtnocyclohexane (60 mg, 0.024 mmol) in DC1-5 (5 mL) was added (3-trifluoromethyl-
phenylsulfinyl)-acetic acid (60 mg, 1 eq.), followed by HATU (85 mg, 1.1 eq.), and Et3N (30 j^L).
The reaction was stirred for 16 h at room temperature and concentrated. The residue was purified
by column chromatography to give A^-(cz5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-{[3-(trifluoromethyl)phenyl]sulfinyI} acetamide (52 mg, 45%), which was
converted to HC1 salt with 4M-HC1 in dioxane.
ESI MS m/e 484 M + HVH NMR (400 MHz, DMSO-6) 5 11.7 (bs, 1 H), 8.08 (d, 1 H, J= 6.4
Hz), 7.99 (m, 2 H), 7.92 (d, 1 H, J= 8.0 Hz), 7.90 (bs, 1 H), 7.82 (t, 1 H, J= 8.0 Hz), 7.59 (s, 1 H),
3.94 (d, 1 H, J= 12.8 Hz), 3.86 (d, 1 H, J= 12.8 Hz), 3.80 (bs, 1 H), 3.68 (bs, 1 H), 3.25 (s, 6 H),
2.23 (s, 3 H), 1.70-1.50 (m, 8 H).

564
Example 2645
2-[(3,4-DichIoropheny1)sulfinyl]-7V-(m-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)acetamidehydrochloride
Step A: Synthesis of 2-I(3,4-dichlorophenyl)sulfinyl]-/V-(m-4-{[4-(dimethyl amino)-5-
methyIpyrimidin-2-yl]amino}cyC1-5hexyl)acetaniide hydrochloride.
Using the procedure of Example 2644, the title compound was obtained.
ESI MS m/e 484 M + H+; ]H NMR (400 MHz, DMSC1-5*) 6 11.9 (bs, 1 H), 8.13 (d, 1 H, J= 6.8
Hz), 7.98 (bs, lH),7.87(s, lH),7.86(d, 1 H, J-8.8 Hz), 7.65 (d, 1 H,7= 8.8 Hz), 7.61 (bs, 1 H),
3.93 (d, 1 H,J= 12.8 Hz), 3.87 (d, 1 H, /= 12.8 Hz), 3.81 (bs, 1 H),3.64(bs, 1 H), 3.25 (s, 6 H),
2.23 (s, 3 H), 1.70-1.50 (m, 8 H).
Example 2646
Ar-(cj5-4-{[4-(Dimethylamino)-S-methylpyrimidin-2-yl]amino}cyclohexyl)-2-{[3-
(trifluoromethyl)phenyl]sulfonyl}acetamide hydrochloride
Step A: Synthesis of A^-(c«-4-{I4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}-
cyclohexyI)-2-{[3-(trifluoromethyl)phenyI]sulfonyl}acetamide hydrochloride.
(3-trifluoromethyl-phenylsulfonyI)-acetic acid ethyl ester was obtained from step B in
Example 2644. The ester was hydrolyzed to (3-trifluoromethyI-phenylsulfonyl)-acetic acid using
the procedure of step C in Example 2644.
lHNMR(400MHz,DMSO-^)S8.22(d, 1H, 7= 8.0 Hz), 8.21 (s, 1 H), 8.14 (d, 1 H, 7= 8.0 Hz),
7.90 (t, 1 H, J= 8.0 Hz), 4.69 (s, 2 H).
To a solution of c/s-4-(4-dimethyIamino-5-methyl-pyrimidin-2-ylamino)-l-
aminocyclohexane (56 mg, 0.023 mmol) in DC1-5 (5 mL) was added (3-trifluoromethyi-
phenylsulfonyl)-acetic acid (60 mg, 1 eq.), followed by HATU (85 mg, 1.1 eq.), and Et3N (30 p.L).
The reaction was stirred for 16 h at room temperature and concentrated. The residue was purified

565
by column chromatography to give iV-(c/5-4-{[4-(dimethy]amino)-5-methyIpyrimidin-2-
yI]amino}cyclohexyl)-2-{[3-(trifluoromethyl)phenyl] sulfonyl}acetamide (50 mg, 45%), which
was converted to HCI salt with 4M HC1 in dioxane.
ESI MS m/e 500 M + H+; lH NMR (400 MHz, DMSO-40 5 11.6 (bs, 1 H), 8.22 (d, 1 H, J= 6.4
Hz), 8.17-8.12 (m, 3 H), 7.90 (t, 1 H, J= 7.6 Hz), 7.87 (bs, 1 H), 7.57 (s, 1 H), 4.45 (s, 2 H), 3.79
(bs, 1 H), 3.61 (bs, 1 H), 3.25 (s, 6 H), 2.23 (s, 3 H), 1.70-1.47 (m, 8 H).
Example 2647
7V-(c/5-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(4-
fluorophenoxy)nicotinamide hydrochloride
Step A: Synthesis of 2-chloro-7V-{c/s-4-(4-dimethylamino-5-methyI-pyrimidin-2-yIamino)-
cyclohexylj-nicotinamide.
To a solution of cw-4-(4-dimethylamino-5-methyl-pyrimidin-2-yIamino)-l-
aminocyclohexane (0.6 g, 2.4 mmol) in DC1-5 (20 mL) was added 2-chloronicotinoyl chloride (0.44
g, 1.01 eq.) and followed by DIEA (0.4 mL, -1.1 eq.). The reaction was stirred overnight at room
temperature, washed with sat-NaHCO3 (2x) and water (Ix), dried with MgSO4, and concentrated.
The crude residue was purified by column chromatography to give 2-chloro-iV-[c^4-(4-
dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-nicotinamide (0.57 g, 65 %).
ESI MS m/e 389 M + H+; !H NMR (400 MHz, CDC13) 5 8.72 (bs, 1 H), 8.47 (d, 1 H, J= 5.0 Hz),
7.98 (d, 1 H,J= 7.0 Hz), 7.32 (dd, 1 U,J= 8.0 and 5.0 Hz), 7.28 (s, 1 H), 6.88 (d, 1 H, /= 8.0 Hz),
4.18 (m, 2 H), 3.27 (s, 6 H), 2.23 (s, 3 H), 1.90-1.80 (m, 8 H).
Step B: Synthesis of A^ds-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
cyC1-5hexyl)-2-(4-fluorophenoxy)nicotinamide hydrochloride.
A sealed tube containing 2-chloro-7V-[c/5-4-(4-dimethylamino-5-methyl-pyrimidin-2-
ylamino)-cyclohexyl]-nicotinamide (0.35 g, 0.9 mmol), 4-fluorophenol (0.25 g, 2.5 eq.), Cs2CO3

566
(0.33 g, 1.1 eq.), and dioxane{3 mL) was reacted in a Smith microwave synthesizer for I h at 180
°C. The reaction was diluted with DC1-5, washed with sat-NaHCO3 (3x) and water (lx), dried, and
concentrated. The residue was purified by column chromatography (DC1-5:MeOH - 100:0 to 95:5)
to give Ar-[C1-5-4-(4-dimethylamino-5-methyI-pyrimidin-2-ylamino)-cyclohexyl]-2-(4-fluoro-
phenoxy)-nicotinamide (0.33 g, 80 %). The neutral compound was dissolved in DC1-5 (5 mL), and
4M-HCI (0.45 mL, 2.5 eq.) in dioxane was added. After 20 min stirring, removal of the volatile
solvent gave 7V-(c^-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-2-(4-
fluorophenoxy)nicotinamidehydrochloride.
ESI MS m/e 465 M + H+; !H NMR (400 MHz, DMSO Hz), 8.15 (dd, 1 H,J= 5.2 and 2.0 Hz), 8.06 (d, 1 H, J= 6.8 Hz), 8.01 (d, 1 H,J= 7.6 Hz), 7.63 (s,
1 H), 7.26-7.18 (m, 5 H), 3.94 (bs, 1 H), 3.88 (bs, 1 H), 3.25 (s, 6 H), 2.21 (s, 3 H), 1.72 (bs, 8 H).
Example 2648
2-(2-Bromophenoxy)-Ar-(C1-5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamidehydrochloride
Step A: Synthesis of 2-(2-bromophenoxy)-Ar-(c/5-4-{[4-(dimethylamino)-5-methylpyrimidin-
2-yl]amino}cyclohexyl)nicotinamide hydrochloride.
Using the procedure of Example 2647, the title compound was obtained.
ESI MS m/e 525 M + *T; !H NMR (400 MHz, DMSO-cfc) 5 11.8 (bs, 1 H), 8.20 (d, 1H,J= 7.6
Hz), 8.16-8.11 (m, 2 H), 7.96 (bs, 1 H), 7.70 (dd, 1 H, J= 8.0 and 1.6 Hz), 7.60 (s, 1 H), 7.47-7.38
(m, 2 H), 7.25-7.19 (m, 2 H), 3.97 (bs, 1 H), 3.89 (bs, 1 H), 3.24 (s, 6 H), 2.22 (s, 3 H), 1.74 (bs, 8
H).
Example 2649
2-(4-Bromophenoxy)-7V-(m-4-{[4-(dimethylamino)-5-methylpyrimidin-2-

567
yl]amino}cyclohexyl)nicotinamide hydrochloride
Step A: Synthesis of 2-(4-bromophenoxy)-A/-(ci.y-4-{[4-(dimethylamino)-5-methylpyriniidin-
2-yl]amino}cyclohexyl)nicotinamide hydrochloride.
Using the procedure of Example 2647, the title compound was obtained.
ESI MS m/e 525 M + HVH NMR (400 MHz, DMSO-afc) 5 11.9 (bs, 1 H), 8.28 (d, 1 H, J= 7.0
Hz), 8.12 (dd, 1 H,7 = 4.4 and 1.6 Hz), 7.97 (d, 1 H, J= 7.6 Hz), 7.91 (bs, 1 H), 7.56 (bs, 1 H),
7.54 (d, 2 H,/-8.8 Hz), 7.17 (m, 1 H), 7.14 (d, 2 H, J= 8.8 Hz), 3.87 (bs, 1 H), 3.81 (bs, 1 H),
3.19 (s, 6 H), 2.16 (s, 3 H), 1.65 (bs, 8 H).
Example 2650
2-(4-Chlorophenoxy)-iV-(C1-5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide hydrochloride
Step A: Synthesis of 2-(4^hlorophenoxy)-A^/s-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide hydrochloride.
Using the procedure of Example 2647, the title compound was obtained.
ESI MS m/e 481 M + fT; *H NMR (400 MHz, DMSO-6) 5 11.8 (bs, 1 H), 8.27 (d, 1 H, .7=6.6
Hz), 8.12 (dd, lH,y= 4.8 and 1.6 Hz), 7.97 (dd, lH,/= 7.0 and 1.6 Hz), 7.86 (bs, 1 H), 7.55 (s, 1
H), 7.41 (d, 2 H, J= 8.8 Hz), 7.20 (d, 2 H, J= 8.8 Hz), 7.17 (m, 1 H), 3.88 (bs, 1 H), 3.81 (bs, 1 H),
3.19 (s, 6 H), 2.16 (s, 3 H), 1.65 (bs, 8 H).
Example 2651
2-[(5-chloropyridin-3-yI)oxy]-Ar-(cw-4-{[4-(dimethylamino)-5-methyIpyrimidiii-2-
yl]amino}cyclohexyi)nicotinamide hydrochloride

568
Step A: Synthesis of 2-[(5-chloropyridin-3-yl)oxy]-Af-(c«-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)nicotinamide hydrochloride.
Using the procedure of Example 2647, the title compound was obtained.
ESI MS m/e 482 M + H+; 'H NMR (400 MHz, DMSO-^) 6 11.6 (bs, 1 H), 8.46 (s, 1 H), 8.31 (d, 1
H, J= 1.6 Hz), 8.01 (bin, 1 H), 7.83 (t, 1 H, J= 2.0 Hz), 7.56 (d, 1 H, J= 5.2 Hz), 7.49 (bm, 1 H),
7.25 (bs, 1 H), 6.07 (bs, 1 H), 5.74 (s, 1 H), 4.51 (bs, 1 H), 4.00 (bs, 1 H), 3.23 (s, 6 H), 2.19 (s, 3
H), 1.90 (m, 2 H), 1.75 (m, 4 H), 1.39 (m, 2 H).
Example 2652
2-(/er/-butylthio)-Ar-(ci5-4-{[4-(dimethylainino)-5-methylpyrimidin-2-yl]amino}-
cyclohexyl)nicotinamide hydrochloride
Step A: Synthesis of 2-(^rt-butylthio)-Ar-(ci5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide hydrochloride.
A sealed tube containing 2-chloro-A^-[cw-4-(4-dimethylamino-5-methyl-pyrimidin-2-
ylamino)-cyclohexyl]-nicotinamide (70 mg, 0.018 mmol), 2-methyl-2-propanethiol (80 mg, 5 eq.),
CS2CO3 (60 mg, 1.1 eq) in dioxane (0.8 mL) was reacted in a Smith microwave synthesizer for 1.5
h at 180 °C. The reaction was diluted with DC1-5, washed with sat-NaHCC>3 (3x) and water (Ix),
dried, and concentrated. The residue was purified by column chromatography (DC1-5:MeOH =
100:0 to 95:5) to give 2-(rer/-butylthio)-A'-(c/5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yijamino} cyclohexyl)nicotinamide (50 mg, 62 %), which was converted to HCI salt.
ESI MS m/e 443 M + H+; *H NMR (400 MHz, DMSO-cfe) 5 12.2 (bs, 1 H), 8.47 (dd, 1 H, J= 4.8
and 1.6 Hz), 8.40 (d, 1 H, J= 6.0 Hz), 8.00 (bm, 1 H), 7.62 (s, 1 H),7.56(dd, 1 H,J = 7.6and 1.6
Hz), 7.15 (m, 1 H), 3.90 (bs, 2 H), 3.25 (s, 6 H), 2.21 (s, 3 H), 1.80-1.65 (m, 8 H), 1.49 (s, 9 H).

569
Example 2653
iV-(C1-5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]aniino}cyclohexyl)-2-
(propylthio)nicotinamidehydrochloride
Step A: Synthesis of Ar-(cw-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-(propyIthio)nicotinamide hydrochloride.
Using the procedure of Example 2652, the title compound was obtained.
ESI MS m/e 429 M + H+; 'H NMR (400 MHz, DMSO-4,) 8 12.4 (bs, 1 H), 8.44 (m, 2 H), 8.04 (d,
1 H, J= 6.8 Hz), 7.63 (d, 2 H, J= 6.4 Hz), 7.12 (m, 1 H), 3.85 (bs, 2 H), 3.24 (s, 6 H), 3.06 (t,2H,
/== 6.8 Hz), 2.21 (s, 3 H), 1.83-1.65 (m, 8 H), 1.62 (m, 2 H), 0.95 (t, 3 H, J= 12 Hz).
Example 2654
A'-(cw-4-{[4-(DimethyIamino)-5-methylpyrimidin-2-yI]amino}cyclohexyI)-2-
(isopropylthio)nicotinamide hydrochloride
Step A: Synthesis of Af-(ci$-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}-
cyC1-5hexyl)-2-(isopropylthio)nicotinamide hydrochloride.
Using the procedure of Example 2652, the title compound was obtained.
ESI MS m/e 429 M + H+; !H NMR (400 MHz, DMSO-6) 5 12.2 (bs, 1 H), 8.46 (dd, 1 H, J= 4.8
and 1.6 Hz), 8.42 (bs, 1 H), 8.02 (d, \H,J= 6.4 Hz), 7.62 (m, 2 H), 7.12 (m, 1 H), 3.95 (sept, 1 H,
J= 6.4 Hz), 3.83 (bs, 2 H), 3.25 (s, 6H), 2.21 (s, 3 H), 1.82-1.65 (m, 8 H), 1.30 (d, 6 H,J= 6.8
Hz).
Example 2655
2-(/ert-Butylsulfinyl)-Ar-(cw-4-{I4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide

570
Step A: Synthesis of 2-(^r/-butylsuIfinyl)-A'-(c/y-4-{(4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide.
To a solution of Ar-[m-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyc]ohexyl]-2-
tert-buty\ sulfanyl-nicotinamide (30 mg, 0.07 mmol) in DC1-5 (5 mL) was added MCPBA (16 mg,
1.1 eq) at 0 °C. The reaction was stirred for an additional 2 h at progress by ESI MS. The reaction was diluted with DC1-5, washed with sat.-NaHCO3 (2x) and
water (Ix), dried, concentrated, and purified by column chromatography (DC1-5:MeOH = 100:0 to
94:6). 26 mg(85 %) of 2-(rer/-butylsulfinyl)-7Vr-(m-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide was isolated.
ESI MS m/e 459 M + rf; ]H NMR (400 MHz, CDC13) 5 8.71 (dd, 1 H, J = 4.8 and 1.6 Hz), 8.54 (d,
1 H, J = 6.8 Hz), 8.20 (d, 1 H, J= 8.0 Hz), 7.61 (s, 1 H), 7.43 (dd, 1 H, J= 8.0 and 4.0 Hz), 5.03 (d,
1 H, J= 6.0 Hz), 4.12 (bs, 1 H), 3.98 (bs, 1 H), 2.99 (s, 6 H), 2.12 (s, 3 H), 1.87-1.75 (m, 8 H),
1.23 (s, 9 H).
Example 2656
2-[(3,4-DifluorophenyI)sulfonylJ-Ar-(c/s-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide hydrochloride
Step A: Synthesis of A^[c/y-4-(4-dimethylamino-5-methyI-pyrimidin-2-ylamino)-cyclohexyl]-
2-(3,4-difluorophenyl)-suIfanyl-nicotinamide.
A sealed tube containing 2-chloro-A'-[c/5-4-(4-dimethylamino-5-methyl-pyrimidin-2-
ylamino)-cyclohexyl]-nicotinamide (100 mg, 0.025 mmol), 3,4-difluorothiophenoI (90 mg, 2.5 eq.),
Cs2CO3 (150 mg, 2 eq), and dioxane (2 mL) was reacted in a Smith microwave synthesizer for 1.0
h at 180 °C. The reaction was diluted with DC1-5, washed with sat-NaHCO3 (3x) and water (lx),
dried, and concentrated. The residue was purified by column chromatography (DC1-5:MeOH =
100:0 to 95:5) to give A^tc/s^-^-dimethylamino-S-methyl-pyrimidin^-ylaminoJ-cyC1-5hexyl]^-

571
(3,4-difluorophenyI)-sulfanyl-nicotinamide (70 mg, 55 %).
ESI MS m/e 499 M + H+; 'H NMR (400 MHz, CDC13) 5 8.34 (dd, 1H,J= 4.8 and 1.6 Hz), 7.79
(dd, 1 H, J= 12 and 2.0 Hz), 7.62 (s, 1 H), 7.35 (m, 1 H), 7.25 (m, 1 H), 7.16
(m, 1 H),7.08(dd, 1 H, J= 7.6 and 4.8 Hz), 6.28 (d, 1 H, J= 12 Hz), 4.71 (d, 1 H,J=7.2Hz),
4.18 (m, 1 H), 3.97 (m, 1 H), 3.02 (s, 6 H), 2.13 (s, 3 H), 1.92-1.85 (m, 4 H), 1.80-1.74 (m, 4 H).
Step B: Synthesis of 2-[(3,4-difluorophenyI)sulfonyl]-A^-(dj-4-{[4-(dimethylainino)-5-
methylpyrimidin-2-y]]amino}cyclohexyl)nicotinamide hydrochloride.
To a solution of A^-[ci5^-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
2-(3,4-difluorophenyl)-sulfanyI-nicotinamide (45 mg, 0.09 mmol) in DC1-5 (6 mL) was added
MCPBA (77 %, 31 mg, 2 eq.) at 0 °C under Ar atmosphere. The reaction was stirred overnight,
washed with sat.-NaHCO3 (2 x) and water, concentrated, and purified by column chromatography
(DC1-5:MeOH = 100:0 to 94:6). 25 mg (53 %) of 2-[(3,4-difluorophenyl)suIfonyl]-tf-(c«-4-{[4-
(dimethylamino)-5-methylpyrimidin-2-yI]amino} cyclohexyl)nicotinamide was isolated and
converted to its HC1 salt.
ESI MS m/e 531 M + ¥t; lH NMR (400 MHz, DMSC1-50 5 11.8 (bs, 1 H), 8.70 (m, 2 H), 8.04 (m,
1 H), 7.95 (dd, 1 H, J= 7.6 and 1.6 Hz), 7.89 (m, 1 H), 7.78-7.70 (m, 2 H), 7.60 (s, 1 H), 3.95 (bs,
1 H), 3.87 (bs, 1 H), 3.25 (s, 6 H), 2.22 (s, 3 H), 1.76 (bs, 8 H).
Example 2657
Ar-(3,4-Difluorophenyl)-ArT-(c/s-4-{(4-(dimethylamino)-5-methyIpyrimidin-2-
ylJamino}cyclohexyl)-iV-methylurea trifluoroacetate
Step A: Synthesis of ethyl 3,4-difluorophenylcarbamate.
3,4-Difluoroaniline (2.8 mL, 28 mmol) and 7V,Af'-diisopropylethylamine (5.4 mL, 31
mmol) were dissolved in 10 mL of anhydrous THF, and cooled to 0°C in an ice bath. Ethyl
chloroformate (5.4 mL, 31 mmol) was added slowly into the stirring solution over the ice bath.

572
The solution was allowed to warm up to room temperature and stir for 30 minutes. The solvent
was removed via vacuo and the crude solid was purified by column chromatography using ethyl
acetate and hexane mixture (3:97) to yield ethyl 3,4-difIuorophenylcarbamate as an off-white solid.
(5.59 g, 99%)
ESI MS m/z 202.1 (M + JT) ; 'HNMR(400MHz, DMSO-d6) 5 9.79 (s, 1H), 7.55-7.50 (m, 1H),
7.29-7.22 (m, 1H), 7.16-7.15 (m, 1H), 4.10 (q, J= 12 Hz, 2H), 1.22 (t,J= 7.2 Hz, 3H).
Step B: Synthesis of (3,4-difluoro-phenyl)-methyl-amine.
Lithium aluminum hydride (2.2 g, 56 mmol) was placed in a 500 mL round bottom flask.
THF (100 mL) was syringed into the flask under argon. The solution was cooled to 0°C in an ice
bath. To the ice-cold solution, 3,4-dtfluorophenylcarbamate (5.59 g, 28 mmol) was added slowly
into the flask. The solution was refluxed for 3 hours. After cooling the reaction mixture to 0°C,
H2O (3 mL), 1 N NaOH (3 mL), and then more H2O (15 mL) were added for quenching. The
precipitate was filtered off and THF was evaporated from the filtrate. The crude was dissolved in
150 mL of ethyl acetate, washed with water, and dried over Na2SO4. The organic solvent was
removed via vacuo to yield (3,4-difluoro-phenyl)-methyl-amine as a light brown oil. (2.86 g, 71%)
ESI MS m/z 144.2 (M + >f) ; !H NMR (400 MHz, CDC13) 5 7.04-6.97 (m, 1H), 6.45-6.39 (m,
1H), 6.32-6.28 (m, 1H), 3.69 (b, 1H), 2.86 (s, 3H).
Step C: Synthesis of Ar-(3,4-difluorophenyI)-iV-(c/$-4-{[4-(dimethylamino)-5-methyl-
pyrimidin-2-yl]amino}cyclohexyI)-iV-methyliirea trifluoroacetate.
cis-[4-(4-dimethIamino-5-methyl-pyrimidin-2-ylamino) cyclohexylj-carbamic acid tert-buty\ ester
(100 mg, 0.402 mmol) and 1,1 '-carbonyldiimidazole (78.1 mg, 0.482 mmol) were dissolved in 1
mL of methylene chloride and allowed to stir at room temperature overnight. To the vial, (3,4-
difluoro-phenyl)-methyl-amine (88 mg, 0.603 mmol) was added. The solution was heated via
Smith Synthesizer at 130°C for 15 minutes. The solvent was evaporated, and 1 mL of methanol
was added to the crude. The crude was purified by HPLC to yield ^-(S^-difluorophenyO-iV^cw-
4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-yV-methylurea trifluoroacetate

573
as a white solid. (47.8 mg, 22%)
ESI MS m/z 419.3 (M + H") ; !HNMR(400MHz, CDC13) 5 14.0 (s, 1H), 8.62 (d, J= 6.4 Hz,
1H), 7.29-7.21 (m,2H), 7.13-7.01 (m,2H),4.61 (bs, lH),4.10(m, lH),3.78(m, 1H), 3.46-3.29 (b,
3H), 3.24 (s, 6H)5 2.24 (s, 3H), 1.77-1.56 (m, 8H).
Example 2658
7V-[(c«-4-{[4-(Dimethylamino)-6-methylpyrimidin-2-yl]aniino}cyclohexyl)methyl]-3,5-
bis(trifluoromethyl)benzamide hydrochloride
Step A: Synthesis of ^-(m^-amino-cyclohexylmethyO-SjS-bistrifluoromethyl-benzamide
trifluoroacetate.
To a solution of c/5-(4-aminornethyl-cyclohexyl)-carbamic acid tert-butyl ester (1.1 g, 4.8
mmol) in dry benzene (15 mL) was added 3,5-bistrifluoromethyI benzoyl chloride (1.33 g, 1 eq.)
and followed by Et3N (~2 mL) at room temperature under N2. The reaction was stirred for an
additional 2 h at room temperature, washed with sat.-NaHCO3 (3x) and water (lx), dried with
MgSO4, and concentrated. The crude {c/s-{4-[(3,5-Bis-trifluoromethyl-benzoylamino)-methyl]-
cyclohexylj-carbamic acid tert-butyl ester was pure enough to use for the next deprotection
without a further purification.
{cj5-{4-[(3,5-Bis-trifIuoromethyi-benzoylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl
ester (2.1 g, 4,5 mmol) was dissolved in DC1-5 (10 mL), and TFA (5 mL) was added to the reaction.
After 1.5 h stirring at room temperature, removal of the volatile solvent gave crude 7Vr-(4-amino-
cyclohexylmethyl)-3,5-bis-trifluoromethyl-benzamide trifluoroacetate as a sticky oil. Addition of
water (~40 mL) to the crude product and shaking well for 5 ~ 10 min provided formation of
precipitates, and the ppts were filtered, washed with water, and dried; 1.40 (61 %) of yV-(4-amino-
cyclohexylmethyl)-3,5-bis-trifluoromethyI-benzamide trifluoroacetate was isolated as a white
powder.
ESI MS m/e 369 M + H+; 'H NMR (400 MHz, DMSO-d6) 5 8.97 (bs, 1 H), 8.47 (s, 2 H), 8.29 (s, 1

574
H), 7.78 H).
Step B: Synthesis of Ar-[(c«-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yIJamino}-
cyC1-5hexyl)methyl]-3,5-bis(trifluoromethyl)benzaniidehydrochloride.
A sealed tube containing 2-chloro-4-dimethylamino-6-methyIpyrimidine (0.21 g, 1.2 mmol), N-
(c«-4-amino-cyclohexylmethyl)-3,5-bistrifluoromethyl-benzamide trifluoroacetate (0.6 g, 1 eq.),
DIEA (0.45 mL, 2 eq.), and terf-BuOH (2.5 mL) was reacted for 1.6 h at 185 °C in a Smith
microwave synthesizer. The reaction was diluted with DC1-5, washed with diluted-HCl and water,
dried, and concentrated. The crude product was purified by column chromatography (silica gel;
DC1-5iMeOH = 100:0 to 95:5). 0.3 g (50 %) of A"-[(cw-4-{[4-(dimethylamino)-6-methylpyrimidin-
2-yl]amino}cyclohexyl) methyl]-3,5-bis(trifluoromethyl)benzamide was isolated and converted to
HCl-salt.
ESI MS m/e 504 M + H+; ]H NMR (400 MHz, CDC13) 5 12.8 (bs, 1 H), 8.72 (d, 1 H, J= 8.0 Hz),
8.39 (s, 2 H), 7.93 (s, 1 H), 7.43 (bs, 1 H), 5.70 (s, 1 H), 4.24 (bm, 1 H), 3.49 (t, 2 H, J= 4.4 Hz),
3.22 (s, 3 H), 3.11 (s, 3 H), 2.31 (s, 3 H), 1.91-1.79 (m, 5 H), 1.64-1.56 (m, 4 H).
Example 2659
7V2-{c/$-4-({6-[(3,4-DifluorophenyI)sulfinylJpyrazin-2-yl}amino)cyclohexyl]-Ar4^V4,5-
trimethyIpyrimidine-2,4-diamine
Step A: Synthesis of C1-5-[l-(6-chloro-pyrazin-2-ylamino)-4-(4-dimethyIamino-5-methyl-
pyrimidin-2-ylaimno)]-cyclohexane.
A sealed tube containing c/5-4-(4-dimethylamino~5-methyI~pyrimidin-2-ylamino)-l-
aminocyclohexane hydrochloride (0.2 g, 0.7 mmol), 2,6-dichloropyrazine (0.1 g, 1 eq.), DIEA (0.3
mL, 2 eq.), and IPA (2 mL) was reacted for 1.5 h at 170 °C in a Smith microwave synthesizer. The
reaction was diluted with DC1-5, washed with 1N-HC1 and water, concentrated, and purified by

575
column chromatography (DC1-5:MeOH= 100:0 to 96:4). 0.15 g (61 %)ofc«-[l-(6-chloro-
pyrazin-2-ylamino)-4-(4-dimethylamino-5-methyl-pyrimidin'2-ylamino)]-cyC1-5hexane was
isolated.
ESI MS m/e 362 M + H+; *H NMR (400 MHz, CDC13) 5 8.70 (bs, 1 H), 7.76 (s, 1 H), 7.71 (s, 1 H),
7.29 (s, I H), 5.32 (bs, 1 H), 4.11 (bs, 1 H), 4.00 (bs, 1 H), 3.27 (s, 6 H), 2.23 (s, 3 H), 1.80 (m, 8
H).
Step B: Synthesis of cw-{l-[6-(3,4-difluoro-phenylsulfanyl)-pyrazin-2-ylamino]-4-(4-
dimethylamino-5-methyI-pyrimidin-2-yIamino)}-cyclohexane.
A sealed tube containing c/5-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-l-(6-
chioro-pyrazin-2-ylamino)-cyclohexane (0.1 g, 0.27 mmol), 3,4-difluorothiophenoI (0.1 g, 2.5 eq.),
CS2CO3 (0.15 g, 2 eq.), and dioxane (2 mL) was reacted for 1 h at 180 °C in a Smith microwave
synthesizer. The reaction was diluted with DC1-5, washed with sat-NaHCO3 (3x) and water,
concentrated, and purified by column chromatography to give 85 mg (65 %) of c«-{l-[6-(3,4-
difluoro-phenylsuIfanyl)-pyrazin-2-yIamino]-4-(4-dimethyIamino-5-methyUpyrimidin-2-
ylamino)}-cyclohexane.
ESI MS m/e 472 M + H+; 'H NMR (400 MHz, CDCI3) 5 7.60 (s, 1 H), 7.48 (s, 1 H), 7.42 (m, 2 H),
7.29 (m, 1 H), 7.15 (m, 1 H), 6.70 (bs, 1 H), 5.15 (d, 1 H, J= 7.6 Hz), 4.03 (bs, 1 H), 3.67 (bm, 1
H), 3.16 (s, 6 H), 2.19 (s, 3 H), 1.81-1.61 (m, 8 H).
Step C: Synthesis of jVz-[ci.$-4-({6-[(3,4-difluorophenyl)sulfinyl]pyrazin-2-yl}amino)-
cyC1-5hexyl]-A^^,5-trimethylpyrimidine~2,4-diamine.
To a solution of cw-4-(4-dimethylamino-5-methyI-pyrimidin-2-ylamino)-l-[6-(3,4-
difluoro-phenylsulfanyI)-pyrazin-2-ylamino]-cyclohexane (35 mg, 0.07 mmol) in DC1-5 (5 mL)
was added MCPBA (33 mg, 2 eq.) at room temperature under an Ar atmosphere. The reaction was
stirred overnight, washed with sat-NaHCOj (2x) and water, concentrated, and purified by column
chromatography (DC1-5:MeOH = 100:0 to 95:5). 12 mg (33 %) of JV2-[cz"s-4-({6-[(3,4-
difluorophenyl)sulfinyl]pyrazin-2-yl}amino)cyC1-5hexyl]-7V4,JV4,5-trimethylpyrimidine-2,4-diamine

576
was isolated.
ESI MS m/e 488 M + H+; 'H NMR (400 MHz, CDC13) 5 8.25 (s, 1 H), 7.87 (s, 1 H), 7.63 (m, 1 H),
7.57 (s, I H), 7.53 (m, 1 H), 7.26 (m, 1 H), 5.36 (bs, 1 H), 5.14 (d, 1 H, J= 6.8 Hz), 4.01 (bs, 1 H),
3.82 (bm, 1 H), 3.06 (s, 6 H), 2.15 (s, 3 H), 1.87-1.60 (m, 8 H).
Example 2660
c/5-Ar-[l-(4-Bromophenyl)ethyl]-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide hydrochloride
Step A: Synthesis of cw-Ar-[l-(4-bromophenyl)ethyI]-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyC1-5hexanecarboxamide hydrochloride.
To a solution of c/5-4-(4-dimethyIamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexanecarboxylic acid obtained from step B of Example 2594 (24 mg, 0.08 mmot) in DC1-5 (3
mL) was added l-(4-bromophenyi)-ethyIamine (18 mg, 1 eq.), and followed by HATU (36 mg, 1.1
eq.) and Et3N (20 JUL). The reaction was stirred overnight, concentrated, and purified by column
chromatography (DC1-5:MeOH = 100:0 to 95:5). 16 mg (41 %) of cw-#-[l-(4-bromophenyl)ethyl]-
4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexanecarboxamide was isolated and
converted to HC1 salt.
ESI MS m/e 460 M + H*"; lH NMR (400 MHz, DMSO-d6) 5 11.0 (bs, 1 H), 8.20 (d, 1 H, J = 7.6
Hz), 7.66 (bs, 1 H), 7.50 (s, 1 H), 7.43 (d, 2 H, J= 8.4 Hz), 7.18 (d, 2 H, J= 8.4 Hz), 4.79 (m, 1 H),
3.95 (bs, 1 H), 3.19 (s, 6 H), 2.23 (bs, I H), 2.16 (s, 3 H), 1.70-1.50 (m, 8 H), 1.24 (d, 3 H,/= 7.2
Hz).
Example 2661
iV-[(c/$-4-{[5-methyl-4-(methylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-3,5-
bis(trifluoromethyl)benzamidehydrochloride

577
Step A: Synthesis of (2-ChIoro-5-methyl-pyrimidin-4-yl)-methyl-amine.
2,4- Dichloro-5-methyIpyrimidine (3.8g, 23.4mmo]) in 20ml in CH2CI2 was added 2.0 M
methylamine in methyl alcohol (14.05ml, 28.1mmol) at 0 CC. The reaction mixture was stirred
overnight and then the excess solvent was evaporated off and the material subjected to
chromatography (50% hexanes in ethyl acetate) to yield (2-Chloro-5-methyl-pyrimidin-4-yl)-
methyl-amine (968.7mg, 6.17mmol, 26%) as a white solid.
ESI MS 158.0 M+H+; 'HNMR(400 MHZ, DMSO-d6) 5 7.86 (s, 1H), 7.39 (s, 1H), 2.93-2.92 (d, J
= 4Hz,3H),2.04(s,3H).
Step B: Synthesis of ^-[(^-^{[S-methyl-^methylaminoJpyrimidin^-ylJamino}-
cyC1-5hexyl)methyl]-3,5-bis(trifluoromethyl)benzamidehydrochloride.
To a solution of (2-Chloro-5-methyl-pyrimidin-4-yl)-methyl-amine (200mg, 1.27mmol) in lmL 2-
propanol was added cw-A^-(4-amino-cyclohexylmethyI)-3,5-bis-trifluoromethyI-benzamide in TFA
salt (736mg, 1.52mmol) and DIEA (2.54mmol). The mixture was heated in a microwave
synthesizer at 180°C for 2 hours. The solvent was evaporated and the material subjected to
chromatography (70 ~ 95% ethyl acetate/ hexanes) The combined compound was dissolved in
CH2C12 and was added 2 M HC1 in diethyl ether (5.6ml, 1.42mmol) to yield iV-[(cw-4-{[5-methyI-
4-(methylamino)pyrimidin-2-yl]amino} cyclohexyl)methyl]-3,5-
bis(trifluoromethyl)benzamidehydrochloride (443mg, 0.84mmol, 66%) as a white solid.
ESI MS 490.4 M+H+ ; 'H NMR (400 MHz, DMSO-d6) 5 11.5 (s, 1H), 8.86-8.83 (t, J= 4 Hz, 8 Hz,
1H), 8.32 (s, 2H), 8.11 (s, 1H), 8.03 (bs, 1H), 7.97 (bs, 1H), 7.40 (s, 1H), 3.90 (bs, 1H), 3.24 (s,
3H), 3.06-3.04 (d, J= 8 Hz, 2H), 2.72-2.71 (d, J= 4 Hz, 3H), 1.54 (bs, 4H), 1.42 (m, 4H), 1.20
(2H).
Example 2662
c/s-4-{[4-(DimethyIamino)-5-niethylpyrimidin-2-yl]aniino}-Ar-[(lif)-l-(3-

578
methoxyphenyl)ethyljcyclohexanecarboxamide hydrochloride
Step A: Synthesis of c/5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]ainino}-A/L[(l/f)-l-(3-
methoxyphenyl)ethyl]cyclohexanecarboxamide hydrochloride.
Using the procedure of Example 2660, the title compound was obtained.
ESI MS m/e 412 M + H+; lH NMR (400 MHz, DMSO-^) 5 10.9 (bs, 1 H), 7.98 (d, 1 H, J= 8.0
Hz), 7.53 (bs, 1 H), 6.98 (t, 1 H, J= 8.0 Hz), 6.63 (d, 1 H, J= 7.4 Hz), 6.62 (s, 1 H), 6.54 (d, 2 H, J
= 8.0 Hz), 4.64 (m, 1 H), 3.79 (bs, 1 H), 3.50 (s, 3 H), 3.03 (s, 6 H), 2.08 (bs, 1 H), 1.97 (s, 3 H),
1.60-1.30 (m, 8 H), 1.10 (d, 3 H, J= 6.8 Hz).
Example 2663
m-4-{[4-(Dimethylamino)-5-methylpyrimidiii-2-yl]amino}-Ar-[(lJ?)-l-(l-
naphthyl)ethyljcyclohexanecarboxamide hydrochloride
Step A: Synthesis of m-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yI]amino}-Ar-[(17f)-l-(l-
naphthyl)ethyl]cyclohexanecarboxamide hydrochloride.
Using the procedure of Example 2660, the title compound was obtained.
ESI MS m/e 432 M + H+; ]H NMR (400 MHz, DMSO-d6) 5 11.1 (bs, 1 H), 8.39 (d, 1 H, J = 8.0
Hz), 8.09 (d, 1 H, J= 8.0 Hz), 7.94 (m, I H), 7.82 (d, 1 H, J=> 8.0 Hz), 7.73 (bs, 1 H), 7.56-7.49
(m, 5 H), 5.69 (m, 1 H), 4.01 (bs, 1 H), 3.25 (s, 6 H), 2.33 (bs, 1 H), 2.23 (s, 3 H), 1.85-1.55 (m, 8
H), 1.49 (d, 3 H, 7=6.8 Hz).
Example 2664
Ar-(cw-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-3-methylbenzamide
hydrochloride

579
Step A: Synthesis of/V-(m-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yIJamino}-
cyclohe\yl)-3-niethylbenzamidehydrochloride.
Using the procedure of example 2523, the title compound was obtained.
ESI MS m/e 368 M + H+; lH NMR (400 MHz, DMSO-rf6) 5 12.2 (bs, 1 H), 8.28 (bs, 1 H), 7.98 (bd,
1 H,/ = 6.0 Hz), 7.64 (m, 3 H), 7.31 (s, 1 H), 7.30 (s, 1 H), 3.91 (bs, 1 H), 3.85 (bs, 1 H), 3.25 (s, 6
H), 2.35 (s, 3 H), 2.22 (s, 3 H), 1.85 (bs, 2 H), 1.70 (bs, 6 H).
Example 2665
Ar-{C1-5-4-[(4-Methylquinolin-2-yl)amino]cyclohexyl}-3,5-bis(trifluoromethyl)benzamide
hydrochloride
Step A: Synthesis of c/WV-^-amino-cyclohexyO-S^S-bisttrifluoromethyl^benzamide.
To a solution of as-(4-amino-cyC1-5hexyI)-carbamic acid ter/-butyl ester (3.2 g, 0.015 mol)
in CH2C12 (50 mL) was added DIEA (3.9 mL, 0.022 mol). The mixture was cooled on an ice bath
and 3,5-bis(trifluormethyl)benzoyI chloride (2.9 mL, 0.015 mol) was slowly added. The mixture
was brought to room temperature and stirred for 1 hour. After this time, the solvent and excess
DIEA was evaporated in vacuo. The resulting oil was re-dissolved in CH?C12 (30 mL) and
extracted with H?O (30 mL), 1M NaOH (30 mL), and brine (30 mL). The brine layer was twice
back extracted with CH2CI2 and the organic layers were combined, dried over MgSC>4, and
concentrated. The resulting precipitate was re-dissolved in CH2CI2 (50 mL) and TFA (4.6 mL,
0.060 mol) was added. The solution was stirred at room temperature for 4 hours (or until the
reaction was complete as judged by TLC). The excess solvent was evaporated off and the resulting
oil was dissolved in 30 mL CH?CI2. The organic layer was extracted with 30 mL of a dilute NaOH
(aq) / NaHCO3 (aq) solution (the aqueous layer was confirmed to remain basic during the
extraction using pH paper indicator). The aqueous layer was back extracted twice with CH2CI2
and the organic layers combined, dried overMgSO4, and concentrated. A precipitate formed that
was subsequently filtered and washed with a cold 50% ether in hexanes solution to yield cis-N-(4-

580
amino-cyclohexyl)-3,5-bis(trifluoromethyl)-benzamide (4.0 g, 0.011 mol, 77%) as a white solid.
ESI MS 355.0 M+H+ ; 'HNMR (400 MHz, CD3OD) 5 8.44 (s, 2H), 8.18 (s, 1H), 4.04 (m, 1H),
3.00 (m, 1H), 1.89-1.84 (m,2H), 1.79-1.74 (m, 4H), 1.74-1.64 (m, 2H).
Step B Synthesis of A^-{c«-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}-3,5-
bis(trifluoromethyl)benzamide hydrochloride.
To a solution of 2-chloro-4-methyI-quinoline (326 mg, 1.84 mmol) in 2 mL f-BuOH was added
DIEA (369 uL, 2.12 mmol) and c/5-Ar-(4-amino-cyclohexyl)-3,5-bis(trifluoromethyl)-benzamide
(500 mg, 1.41 mmol). The mixture was then heated in a microwave at 180 °C for 12 hours. The
reaction mixture was cooled and concentrated and the resulting oil was purified by column ( MeOH in CH2C1?). The organic solvents were evaporated and the resulting oil was re-dissolved
into 4 mL CH2CI2 and HC1 (1.4 mL, 2.82 mol) was added. The reaction was stirred for 30 minutes
and the solvent was removed. A precipitate formed that was subsequently filtered and washed with
a cold 50% ether in hexanes solution to yield A'-{c/5-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}-
3,5-bis(trifIuoromethyI)benzamide hydrochloride (620 mg, 1.17 mmol, 83%).
ESI MS 496.4 M+H+ ; 'H NMR (400 MHz, CD3OD) 6 8.47 (s, 2H), 8.21 (s, 1H), 8.05 (d, 1H, J =
8.0 Hz), 7.93 (bs, 1H), 7.82 (t, 1H, J= 7.8 Hz), 7.59 (t, 1H, J= 8.2 Hz), 7.09 (bs, 1H), 4.17 (m, 1H),
4.15 (m, 1H), 2.73 (s, 3H), 2.08-1.95 (m, 8H).
Example 2666
A^cis-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-3-
(trifluoromethoxy)benzamide hydrochloride
Step A: Synthesis of Ar-(C1-5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyI)-3-(trifluoromethoxy)benzamide hydrochloride.
Using the procedure of example 2523, the title compound was obtained.
ESI MS m/e 438 M + W; 'H NMR (400 MHz, CDC13) 5 12.9 (bs, 1 H), 8.59 (bd, 1 H, J= 6.8 Hz),

581
7.69 (s, I H), 7.68 (d, 1 H, J= 8.4 Hz), 7.43 (t, 1 H, J= 8.0 Hz), 7.30 (d, 1 H, J= 7.6 Hz), 7.20 (d,
1 H,y= 5.2 Hz), 6.55 (d, 1 H, J= 8.0 Hz), 4.17 (bs, 1 H), 4.10 (bs, 1 H), 3.29 (s, 6 H), 2.24 (s, 3 H),
1.98-1.83 (m, 6 H), 1.73 (m, 2 H).
Example 2667
7V-(c/5-4-{[4-(Dimethylamino)-5-methyIpyrimidin-2-yl]aminoJcyclohexyl)-4-
(trifluoromethoxy)benzamide hydrochloride
Step A: Synthesis of Ar-(c/y-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-4-(trifluoromethoxy)benzamide hydrochloride.
Using the procedure of example 2523, the title compound was obtained.
ESI MS m/e 438 M + H+; 'H NMR (400 MHz, CDC13) 5 12.3 (bs, 1 H), 8.54 (bd, 1 H, J= 6.8 Hz),
7.86(d,2H,J=8.8Hz), 7.22(d,2H,J=8.8Hz), 7.21 (s, 1 H), 6.68 (d, 1 H,J= 8.0 Hz), 4.17 (bs,
1 H), 4.10 (bs, 1 H), 3.28 (s, 6 H), 2.24 (s, 3 H), 1.95-1.85 (m, 6 H), 1.72 (m, 2 H).
Example 2668
3-Chloro-Ar-(c/s-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
(trifluoromethoxy)benzamide hydrochloride
Step A: Synthesis of 3-chloro-iV-(c/s-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-4-(trifluoromethoxy)benzamide hydrochloride.
Using the procedure of example 2523, the title compound was obtained.
ESIMSm/e472M + HVHNMR(400MHz,CDCl3)5 12.5 (bs, 1 H), 8.37 (bd, 1 H, .7=7.2 Hz),
8.06 (s, 1 H), 7.86 (d, 1 H, J= 8.4 Hz), 7.51 (d, 1 H, J= 8.4 Hz), 7.30 (d, 1 H, J= 8.0 Hz), 7.24 (s,
1 H), 4.17 (bs, 1 H), 4.08 (bm, 1 H), 3.28 (s, 6 H), 2.23 (s, 3 H), 1.92-1.85 (m, 6 H), 1.71 (m, 2 H).

582
Example 2669
4-ChIoro-Ar-(cw-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethyl)benzamide hydrochloride
Step A: Synthesis of 4-chloro-7V-(cw-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-3-(trifluoromethyl)benzamide hydrochloride.
Using the procedure of example 2523, the title compound was obtained.
ESIMSm/e456M + H+;IHNMR(400MHz, CDCI3) 8 12.8 (bs, 1 H), 8.58 (bd, 1 H,J=6.8Hz),
8.19 (s, 1 H), 7.90 (d, 1 H, J= 8.4 Hz), 7.54 (d, 1 H, J= 8.4 Hz), 7.19 (bd, 1 H, J= 5.2 Hz), 6.76 (d,
1 H, J= 8.4 Hz), 4.19 (bs, 1 H), 4.10 (bm, 1 H), 3.29 (s, 6 H), 2.24 (s, 3 H), 1.94-1.83 (m, 6 H),
1.72 (m, 2 H).
Example 2670
3,5-Dichloro-yV-(c/y-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}eyclohexyl)benzamide hydrochloride
Step A: Synthesis of 3^-dichloro-A'-(c/5-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide hydrochloride.
Using the procedure of example 2523, the title compound was obtained.
ESI MS m/e 422 M + H+; ]H NMR (400 MHz, DMSO-^) 5 12.1 (bs, 1 H), 8.50 (bs, 1 H), 8.02 (bd,
1 H,J=5.2Hz),7.86(d,2H,J= 1.6 Hz), 7.77 (t, 1 H, J= 1.6 Hz), 7.63 (s, 1 H),3.90(bs, 1 H),
3.85 (bs, 1 H), 3.25 (s, 6 H), 2.22 (s, 3 H), 1.85 (bs, 2 H), 1.70 (bs, 6 H).
Example 2671
S^-Dichloro-A^^w^-l^-fdimethylamino^S-methylpyrimidin^yljaminoJcyclohexyl)-

583
benzamide hydrochloride
Step A: Synthesis of 3,4-dichloro-Ar-(c/y-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yl]amino}cyclohexyl)benzamide hydrochloride.
Using the procedure of example 2523, the title compound was obtained.
ESI MS m/e 422 M + H+; !H NMR (400 MHz, DM$O-d6) 5 12.2 (bs, 1 H), 8.47 (bs, 1 H), 8.09 (d5
1 H, ,7=2.0 Hz), 8.05 (d, 1 H, 7-6.4 Hz), 7.82 (dd, 1 H, 7=8.0 and 1.6 Hz), 7.71 (d, 1 H, .7=8.4
Hz), 7.63 (s, 1 H),3.90(bs, 1 H),3.85(bs, 1 H), 3.25 (s, 6 H), 2.22 (s, 3 H), 1.85 (bs, 2 H), 1.70 (bs,
6H).
Example 2672
5-Bromo-Ar-(c/5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-2-
furamide
Step A: Synthesis of 5-bromo-/V-(C1-5-4-{[4-(dimethyIamino)-5-niethylpyriniidin-2-
yl]amino}cyclohexyl)-2-furamide.
Using the procedure of example 2523, the title compound was obtained.
ESI MS m/e 422 M + H+; lH NMR (400 MHz, CDC13) 5 7.64 (s, 1 H), 7.02 (d, 1 H, J= 3.6 Hz),
6.41 (d, 1 H, J= 3.6 Hz), 6.23 (bs, 1 H), 4.77 (bs, 1 H), 4.08 (bs, 1 H), 3.96 (bs, 1 H), 3.02 (s, 6 H),
2.14 (s, 3 H), 1.88-1.60 (m, 8 H).
Example 2673
Ar-(c/j-4-{[4-(Dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyC1-5hexyl)-2-
(m ethyls ulfonyl) benzamide

584
Step A: Synthesis of 7V-(c/5-4-{(4-(dimethylamino)-5-methyIpyrimidin-2-
yl]amino}cyclohexyl)-2-(methylsulfonyl)benzamide.
Using the procedure of example 2523, the title compound was obtained.
ESI MS m/e 432 M + H+; !H NMR (400 MHz, CDC13) 5 8.02 (d, 1 H, J = 7.6 Hz), 7.69 (t, 1 H, J =
8.0 Hz), 7.59 (t, 2 H, J= 7.6 Hz), 6.39 (d, \ H, J= 8.0 Hz), 6.34 (bs, 1 H), 4.10 (bs, 2 H), 3.33 (s, 3
H), 3.25 (s, 6 H), 2.25 (s, 3 H), 1.93-1.71 (m, 8 H) .
Example 2674
7V-(m-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
(m ethyls ulfonyl)benzamide
Step A: Synthesis of Ar-(c/s-4-{[4-(dimethylamino)-5~methylpyrimidin-2-
yl]amino}eydohexyl)-3-(methyIsulfonyI)benzamide.
Using the procedure of example 2523, the title compound was obtained.
ESI MS m/e 432 M + H4"; !H NMR (400 MHz, CDC13) 8 8.40 (s, 1 H), 8.18 (d, 1 H, J= 7.6 Hz),
8.08 (d, I H, J= 7.6 Hz), 7.67 (t, 1 H, J = 7.6 Hz), 7.34 (s, 1 H), 6.99 (d, 1 H, J= 8.0 Hz), 6.57 (bd,
1 H, J= 6.4 Hz), 4.17 (bm, 2 H), 3.32 (s, 6 H), 3.16 (s, 3 H), 2.27 (s, 3 H), 1.90-1.71 (m, 8 H).
Example 2675
Ar-(ci5-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
(methylsulfonyl)benzamide
Step A: Synthesis of Ar-(C1-5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyl)-4-(methylsulfonyI)benzamide.
Using the procedure of example 2523, the title compound was obtained.
ESI MS m/e 432 M + H+; 'H NMR (400 MHz, CDC13) 5 8.04 (d, 2 H, J = 8.4 Hz), 7.98 (d, 2 H, J =

585
8.4 Hz), 7.28 (s, 1 H),6.86(d, 1 H, 7= 8.4 Hz), 6.41 (d, 1 H, J= 7.6 Hz), 4.14 (bm, 2 H), 3.32 (s, 6
H), 3.07 (s, 3 H), 2.27 (s, 3 H), 1.90-1.71 (m, 8 H).
Example 2676
Methyl 2-{I(cw-4-{[4-(dimethylamino)~5-methylpyrimidin-2-yl]amino}cyclohexyl)-
amino]carbonyl}benzoate
Step A: Synthesis of methyl 2-{[(as-4-{[4-(dimethylamino)-5-methyIpyriinidin-2-
yl]amino}cyclohexyl)amino]carbonyl}benzoate.
Using the procedure of example 2523, the title compound was obtained.
ESI MS m/e 428 M + H+; *H NMR (400 MHz, CDC13) 5 8.10 (bs, 1 H), 7.87 (d, 1 H, J= 7.6 Hz),
7.52 (t, 1 H, J= 7.6 Hz), 7.46 (m, 2 H), 7.30 (s, 1 H), 6.56 (d, 1 H, J= 8.0 Hz), 4.13 (bra, 2 H),
3.87 (s, 3 H), 3.24 (s, 6 H), 2.22 (s, 3 H), 1.93-1.75 (m, 8 H).
Example 2677
Methyl 3-{[(c«-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-
amino]carbonyl}benzoate
Step A: Synthesis of methyl 3-{[(cw-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)amino]carbonyl}benzoate.
Using the procedure of example 2523, the title compound was obtained.
ESI MS m/e 428 M + H^ 'H NMR (400 MHz, CDC13) 5 8.48 (s, lH),8.17(bs, 1 H), 8.14 (d, 1 H,
J= 7.6 Hz), 8.08 (d, 1 H, J= 7.6 Hz), 7.51 (t, 1 H, J= 8.0 Hz), 7.31 (s, 1 H), 7.16 (d, 1 U,J= 7.6
Hz), 4.14 (bm, 2 H), 3.94 (s, 3 H), 3.26 (s, 6 H), 2.23 (s, 3 H), 1.93-1.73 (m, 8 H).

586
Example 2678
2-{[(C1-5-4-{[4-(Dimethylamino)-5-methyIpyrimidin-2-yI]amino}cyclohexyl)-
aminojcarbonyl}benzoic acid hydrochtoride
Step A: Synthesis of 2-{[(m-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)amino]carbonyl}benzoic acid hydrochloride.
Using the procedure of example 2523, the title compound was obtained.
ESI MS tn/e 398 M + H+; 'H NMR (400 MHz, DMSO-d6) 5 12.5 (bs, 2 H), 8.32 (bs, 1 H), 8.04 (d,
lH,J = 6.4Hz),7.80(d, lH,y = 7.6Hz), 7.68 (s, 1 H), 7.58 (m, 1 H), 7.51 (t, 1 U,J= 7.6 Hz),
7.39 (d, 1 H, J= 7.6 Hz), 3.89 (bs, 2 H), 3.28 (s, 6 H), 2.25 (s, 3 H), 1.85-1.70 (m, 8 H).
Example 2679
3-{[(cis-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-
aminojcarbonyljbenzoic acid hydrochloride
Step A: Synthesis of 3-{[(cw-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)amino]carbonyl}benzoic acid hydrochloride.
Using the procedure of example 2523, the title compound was obtained.
ESI MS m/e 398 M + H+; *HNMR (400 MHz, DMSO-fifc) 5 13.2 (bs, 1 H), 12.3 (bs, 1 H), 8.59 (bs,
1 H), 8.47 (m, 1 H), 8.16-8.11 (m, 3 H), 7.72 (s, 1 H), 7.64 (t, 1 H,J= 8.0 Hz), 3.95 (bs, 2 H), 3.32
(s, 6 H), 2.29 (s, 3 H), 1.93 (bs, 2 H), 1.78 (bs, 6 H).
Example 2680
Ar-(c/s-4-{[4-(Dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3,4-
difluorobenzamide hydrochloride

587
Step A: Synthesis of A^C1-5-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}-
cyclohexyl)-3,4-difluorobenzamide hydrochloride.
Using the procedure of example 2526, the title compound was obtained.
ESI MS m/e 390 M + H+; *H NMR (400 MHz, DMSO-cfc) 5 12.7 (bs, 1 H), 8.37 (bs, 1 H),
7.93-7.88 (m, 2 H), 7.73 (m, 1 H), 7.51 (dd, 1 H, J= 18.8 and 8.4 Hz), 6.26 (s, 1 H), 3.96 (bs, 1 H),
3.84 (bs, 1 H), 3.17 (s, 3 H), 3.13 (s, 3 H), 2.25 (s, 3 H), 1.85 (bm, 2 H), 1.70 (bs, 6 H).
Example 2681
7V-(c/s-4-{[4-(Dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
bis(trifluoromethyl)benzamide hydrochloric acid
Step A: Synthesis of A'-(c/y-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}-
cyclohexyl)-3,5-bis(trifluoromethyl)benzamide hydrochloric acid.
To a solution of (2-chIoro-6-methyl-pyrimidin-4-yl)-dimethyl-amine (242 mg, 1.41
mmol) in 2 mL /-BuOH was added DIEA (369 uL, 2.12 mmol) and cis-N-(4-am\no-cyclohexyl)-
3,5-bis(trifluoromethyl)-benzamide (500 mg, 1.41 mmol). The mixture was then heated in a
microwave at 180 °C for 1.7 hours. The reaction mixture was cooled and concentrated and the
resulting oil was purified by column ( evaporated and the resulting oil was re-dissolved into 4 mL CH2C12 and HCI (1.4 mL, 2.82 mol)
was added. The reaction was stirred for 30 minutes and the solvent was removed. A precipitate
formed that was subsequently filtered and washed with a cold 50% ether in hexanes solution to
yield ^-(^^-{^-(dimethylamino^-methylpyrimidin^-yljaminojcyclohexyl)^^-
bis(trifluoromethyl)benzamide hydrochloric acid (653 mg, 1.24 mmol, 88%).
ESI MS 490.4 M+H"; 'HNMR (400 MHz, CD3OD) 5 12.58 (bs, 1H), 8.81 (d, 1H, J = 6.4 Hz),
8.50 (s, 2H), 8.30 (s, lH),7.89(bs, 1H), 6.28 (s, 1H), 4.00 (m, lH),3.90(m, 1H), 3.18 (s, 3H),
3.12 (s, 3H), 2.25 (s, 3H), 1.87-1.71 (m, 8H).

588
Example 2682
A^c/s-4-{[4-(Dimethylamino)-6-methylpyrimidin-2-yI]amino}cyC1-5hexyI)-4-
(trifluoromethoxy)benzamide hydrochloride
Step A: Synthesis of iV-(cw-4-{[4-(d i methyl am ino)-6-m ethyIpyrimidin-2 -
yl]amino}cyclohexyl)-4-(trifluoromethoxy)benzamide hydrochloride.
Using the procedure of example 2526, the title compound was obtained.
ESI MS m/e 438 M + H+; *H NMR (400 MHz, CDC13) 5 13.0 (bs, 1 H), 8.52 (bd, 1 H, J= 7.6 Hz),
7.87 (d, 2 H, J= 8.8 Hz), 7.23 (d, 2 H, J = 8.8 Hz), 6.84 (d, 1 H, J= 8.0 Hz), 5.72 (s, 1 H), 4.22
(bm, 1 H),4.11(bm, 1 H), 3.24 (s, 3 H), 3.12 (s, 3 H), 2.34 (s, 3 H), 1.95-1.85 (m, 6 H), 1.72 (m, 2
H).
Example 2683
3-Chloro-A'-(C1-5-4-{[4-(dimethylamino)-6-methylpyrimidiii-2~y1]amino}cyclohexyl)-4-
(trifluoromethoxy)benzamide hydrochloride
Step A: Synthesis of 3-chloro-Af-(c«-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyC1-5hexyI)-4-(trifluoromethoxy)benzamide hydrochloride.
Using the procedure of example 2526, the title compound was obtained.
ESI MS m/e 472 M + H+; 'H NMR (400 MHz, CDC13) 5 12.9 (bs, 1 H), 8.52 (d, 1 H, J= 7.6 Hz),
7.96 (d, 1 H, J= 2.4 Hz), 7.73 (dd, 1 H, J= 8.8 and 2.0 Hz), 7.34 (d, 1 H, J= 8.4 Hz), 6.59 (d, 1 H,
J= 8.0 Hz), 5.72 (s, I H), 4.22 (bm, 1 H), 4.10 (bm, 1 H), 3.24 (s, 3 H), 3.12 (s, 3 H), 2.34 (s, 3 H),
1.95-1.83 (m, 6 H), 1.72 (m, 2 H).
Example 2684

589
4-Chloro-Ar-(m-4-{[4-(dimethylamiino)-6-methylpyriinidin-2-yl]amino}cyclohexyl)-
benzamide hydrochloride
Step A: Synthesis of 4-chloro-iV-(as-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yljamino}cyc)ohexyl)benzamide hydrochloride.
Using the procedure of example 2526, the title compound was obtained.
ESI MS m/e 388 M + H4"; lH NMR (400 MHz, CDCI3) 5 13.1 (bs, 1 H), 8.57 (bd, 1 H, J= 8.0 Hz),
7.73 (d, 2 H, J= 8.4 Hz), 7.37 (d, 2 H,J= 8.4 Hz), 6.46 (d, 1 H, J= 6.0 Hz), 5.71 (s, 1 H), 4.20 (bs,
1 H), 4.10 (bs, 1 H), 3.24 (s, 3 H), 3.12 (s, 3 H), 2.34 (s, 3 H), 1.94-1.82 (m, 6 H), 1.73 (m, 2 H).
Example 2685
3,4-Dichloro-Ar-(c«-4-{[4-(dimethylamino)-6-inethylpyrimidin-2yl]ainino}cyclohexyl)-
benzamide hydrochloride
Step A: Synthesis of 3,4-dichloro-7V-(c«-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide hydrochloride.
Using the procedure of example 2526, the title compound was obtained.
ESI MS m/e 422 M + H+; *H NMR (400 MHz, CDC13) 5 13.0 (bs, 1 H), 8.51 (d, 1 H, y = 7.6 Hz),
7.94 (d, 1 H, 7= 2.0 Hz), 7.64 (dd, 1 H, J= 8.4 and 2.0 Hz), 7.47 (d, 1 H, y= 8.4 Hz), 6.88 (d, 1 H,
J= 8.8 Hz), 5.72 (s, 1 H), 4.22 (bm, 1 H), 4.09 (bm, I H), 3.24 (s, 3 H), 3.13 (s, 3 H), 2.34 (s, 3 H),
1.94-1.82 (m, 6 H), 1.72 (m, 2 H).
Example 2686
AL(C1-5-4-{[4-(Dimethylamino)-6-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-3,5-
dimethoxy benzamide

590
Step A: Synthesis of 7V-(C1-5-4-{[4-(dimethylamino)-6-methylpyriinidin-2-yl]aniino}-
yclohexyl)-3,5-dimethoxybenzamide.
Using the procedure of example 2526, the title compound was obtained.
ESI MS m/e 414 M + H+; 'H NMR (400 MHz, CDC13) 5 6.88 (d, 2 H, J= 2.0 Hz), 6.57 (t, 1 H, J=
2.0 Hz), 6.15 (d, 1 H, J= 7.6 Hz), 5.69 (s, 1 H), 5.10 (bs, 1 H), 4.06 (bm, 2 H), 3.82 (s, 6 H), 3.04
(s, 6 H), 2.21 fs, 3 H), 1.90-1.81 (m, 6 H), 1.67 (m, 2 H).
Example 2687
5-Bromo-7V-(C1-5-4-{[4-(dimethylamino)-5-methylpyriinidin-2-yl]ainino}cyclohexyl)-
nicotinamide hydrochloride
Step A: Synthesis of 5-bromo-A^-(c«-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
y]]amino}cyclohexyl)nicotinamide hydrochloride.
Using the procedure of example 2526, the title compound was obtained.
ESI MS 433.2 M+H+ ; 'H NMR (400 MHz, DMSO-d6) 6 12.2 (s, 1H), 8.85 (d, J= 4 Hz,lH), 8.73
(d, J=4 Hz, 1H), 8.51 (bs, 1H), 8.34-8.33 (m, 1H)5 7.55 (bs, 1H), 3.76 (bs, 2H), 3.14 (bs, 6H), 2.10
(s, 3H), 1.74-1.59 (m,8H).
Example 2688
Ar-(c/5-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-[2,2,2-trifluoro-l-
hydroxy-l-(trifluoromethyl)ethyl]benzamide hydrochloride
Step A: Synthesis of Ar-(c/y-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yI]amino}-
cyclohexyl)-4-[2,2,2-trifluoro-l-hydroxy-l-(trifluoromethyl)ethyl]benzamide hydrochloride.
Using the procedure of example 2526, the title compound was obtained.
ESI MS 520.4 M+H+ ; 'H NMR (400 MHz, DMSO-d6) 5 12.0 (s, 1H), 8.84 (s, 1H), 8.36 (bs, 1H),

591
7.91 (bs, 1H), 7.88 (d, J= 8 Hz, 2H), 7.73-7.71 (d, J= 8 Hz, 2H), 7.60 (s, 1H), 3.85 (bs, 2H), 3,23
(s, 6H), 2.20 (s, 3H), 1.82 (m, 2H), 1.68 (m, 6H).
Example 2689
3-Bromo-4-chloro-/V-(C1-5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide hydrochloride
Step A: Synthesis of 3-bromo-4-chloro-Ar-(c/y-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide hydrochloride.
Using the procedure of example 2526, the title compound was obtained.
ESI MS 466.0 M+}f ; lH NMR (400 MHz, DMSO-d6) 5 12.0 (s, 1H), 8.32-8.31 (d, J= 4 Hz, 1H),
8.08-8.07 (d,J= 2 Hz, 1H), 7.88-7.86 (d,J= 8 Hz, 1H), 7.73-7.70 (dd, J1 = 4 Hz, J2 = 4 Hz, 1H),
7.57-7.55 (d, J= 8 Hz, 1H ), 7.49 (s, 1H), 3.76-3.69 (m, 2H), 3.16 (s, 6H), 2.07 (s, 3H), 1.70 (bs,
2H), 1.55(bs,6H).
Examples 2690-2711
Compounds 2690 to 2711 were prepared in a similar manner as described in Example 2590
using the appropriate acid chloride and amine intermediate from Step B.
Examples 2712-2731
Compounds 2712 to 2731 were prepared in a similar manner as described in Example 2591
using the appropriate acid chloride and amine intermediate from Step A.
Examples 2732-2750
Compounds 2732 to 2750 were prepared in a similar manner as described in Example 2592
using the appropriate acid chloride and amine intermediate from Step A.

592
Examples 2751-2770
Compounds 2751 to 2770 were prepared in a similar manner as described in Example 2593
using the appropriate acid chloride and amine intermediate from Step B.
Examples 2771-2794
Compounds 2771 to 2794 were prepared in a similar manner as described in Example 2594
using the appropriate amine and the carboxylic acid intermediate from Step B.
Examples 2795-2823
Compounds 2795 to 2823 were prepared in a similar manner as described in Example 2527
using the appropriate amine and the carboxylic acid intermediate from Step B.
Examples 2824-2864
Compounds 2824 to 2864 were prepared in a similar manner as described in Example 2607
using the appropriate acid chloride and the amine intermediate from Step D.
Examples 2865-2866
Compounds 2865 and 2866 were prepared in a similar manner as described in Example
2611 using the appropriate benzaldehyde and the amine from Step A.
Examples 2867-2869
Compounds 2867 to 2869 were prepared in a similar manner as described in Example 2613
using the appropriate isocyanate and the amine from Step A.
Examples 2870-2875
Compounds 2870 to 2875 were prepared in a similar manner as described in Example 2615
using the appropriate carboxylic acid and the amine from Step A.

593
Example 2876
Compound 2876 was prepared in a similar manner as described in Example 2623 using the
appropriate 4-chloro mandelic acid and the amine of Step A.
Examples 2877-2879
Compounds 2877 to 2879 were prepared in a similar manner as described in Example 2638
using the appropriate phenol and the bromoacetamide intermediate of Step B.
Examples 2880-2884
Compounds 2880 to 2884 were prepared in a similar manner as described in Example 2644
using the appropriate thiophenol.
Examples 2885-2895
Compounds 2885 to 2895 were prepared in a similar manner as described in Example 2647
using the appropriate phenol and the chloropyridyl intermediate of Step A.
Examples 2896-2940
Compounds 2896 to 2940 were prepared in a similar manner as described in Example 2523
using the appropriate acid chloride and the amine of Step C.
Examples 2941-2948
Compounds 2941 to 2948 were prepared in a similar manner as described in Example 2635
using the appropriate iV-methylaniline and the bromoacetamide intermediate from step A.
Examples 2949-2950
Compounds 2949 and 2950 were prepared in a similar manner as described in Example
2619 using the appropriate carboxylic acid and the amine of Step A.

594
Examples 2951-2994
Compounds 2951 to 2994 were prepared in a similar manner as described in Example 2526
using the appropriate acid chloride and the amine of Step C.
Example 2995
Compound 2995 was prepared in a similar manner as described in Example 2628 using
phenylsulfonyl chloride and the amine of Step A.
Examples 2996-3004
Compounds 2996 to 3004 were prepared in a similar manner as described in Example 2632
using the appropriate benzaldehyde and the amine of Step A.
Example 3005
Compound 3005 was prepared in a similar manner as described in Example 2632 using 3-
trifluoromethoxy benzaldehyde and the amine from step C of Example 2526.
Example 3006
Compound 3006 was prepared in a similar manner as described in Example 2642 using
3,4-difluorobenzoyl chloride and the amine from Step C.
Examples 3007-3011
Compounds 3007 to 3011 were prepared in a similar manner as described in Example 2637
using the appropriate phenol and the chloropyridyl intermediate from Step A.
Examples 3012-3020
Compounds 3012 to 3020 were prepared in a similar manner as described in Example 2636
using the appropriate phenol and the chloropyridyl intermediate of Step A.

595
Examples 3021-3029
Compounds 3021 to 3029 were prepared in a similar manner as described in Example 2657
using the appropriate jV-methylaniline and the intermediate prepared in Step C.
Example 3030
Compound 3030 was prepared in a similar manner as described in Example 2595 using
3,4-dichlorobenzoyl chloride and the amine of Step A.
Specific compounds as shown in the Examples and in the Tables herein are represented as
a mono or di-salt, for example, trifluoroacetate, hydrochloride, and the like; or as a free base. It is
understood that these specific representations of the compounds in no way limit the scope of the
invention to the respective salt or free base. For example, a trifluoroacetate salt can be readily
converted to the corresponding free amine by treatment with a sufficient amount of base and if
desired converted to another salt, for example, a pharmaceutically acceptable salt as described
herein.
It is understood that the present invention embraces compounds, as disclosed herein, as
free bases, inorganic salts, and organic salts; and as solvates, and hydrates thereof.
Compounds in the subsequent table are listed specifically as the free base and may have
been specifically isolated as a trifluoroacetate, hydrochloride, or like salt as dictated by the specific
synthetic procedure.

596

Ex. No. compound name MS class
2690 N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino)cyclohexYl)methyl]benzamide 368 (M + H) ">
2691 N-[(cis-4- {[4-(dimethy lamino)-5-methylpyrimidin-2-
yIlamino)cyclohexyl)methyll-4-methvlbenzamide 382 (M + H) ■■>
2692 N-[(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yllamino}cyclohexyI)methyil-3,4-difluorobenzamide 404 (M + H) 2
2693 N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cvC1-5hexyl)methyIl-4-methoxvbenzamide 398 (M + H) 3
2694 N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)methvn-3,5-dimethoxybenzamide 428 (M + H) 1
2695 N- [(c i s-4- {[4-(d i methy lam i no)-5 -methy lpyrim idin-2-
yllamino}cyclohexyl)methyll-3-fluoro-4-methylbenzamide 400 (M + H) 2
2696 N-[(cis-4- {[4-(dimethylamino)-5-methy lpyrimidin-2-
ynamino}cvclohexyI)methyl1-4-fluoro-3-methvlbenzamide 400 (M + H) 2
2697 N-[(cis-4-{[4-fdimethylamino)-5-methylpyrimidin-2-
vl]amino}cyclohexy!)methyn-3-ftrifluoromethyI)benzamide 436 (M + H) 1
2698 N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
ynamino>cyclohexy0methyn-4-(trifIuoromethvI)benzamide 436 (M + H) 3
2699 N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cvclohexyl)methyn-3-(trifluoromethoxy)benzamide 452 (M + H) 2
2700 N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yIlamino}cyclohexyl)methyIM-(trifIuoromethoxy)benzamide 452 (M + H) 2
2701 4-cyano-N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cvclohexyl)methvllbenzamide 393 (M + H) 2
2702 4-bromo-N-[(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yl]amino)cyclohexyl)methyllbenzamide 446 (M + H) 1
2703 4-bromo-N-[(cis-4-{[4-(din)ethylamino)-5-methylpyrimidin-2-
ynamino}cyC1-5hexyI)methyll-3-methvlbenzamide 460 (M + H) 1
2704 3-chloro-N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyl)methyl]-4-fluorobenzamide 420 (M + H) 1
2705 N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyi)methyl]-3-fluoro-4-
(trifluoromethvl>benzamide 454 (M + H) 2
2706 3,5-dichloro-N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyl)methyl]benzamide 436 (M + H) 1
2707 3,4-dichloro-N-[(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yllamino}cyC1-5hexyl)methynbenzamide 436 (M + H) 1
2708 N-[(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino} cyclohexy l)methyl]-2,2-difluoro-1,3-benzodioxole-5-
carboxamide 448 (M + H) 2
2709 N-[(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yllamino}cvclohexyI)methyllbiphenvI-4-carboxamide 444 (M + H) 3
2710 4-chloro-N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
vl]amino}cyclohexyl)methyllbenzamide 402 (M + H) 2
2711 N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)methyll-3,5-dimethoxybenzamide 428 (M + H) 2
2712 N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}methyt)cyclohexvllbenzamide 368 (M + H) 3

597

Ex. No. compound name MS class
2713 N-[cis-4-( {[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}methyl)cyclohexyll-4-methylbenzamide 382 (M + H)
2714 N-[cis-4-( {[4-(dimethylamino)-5-methyipyrimidin-2-
yllamino}methyI)cyclohexyl]-3,4-difluorobenzamide 404 (M + H) 3
2715 N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}methyl)cyclohexyl]-4-methoxybenzamide 398 (M + H) -i
2716 N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}methyl)cyclohexyIl-3,5-dimethoxybenzamide 428 (M + H) 2
2717 N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-
vllamino}methyl)cyclohexyl]-3-fluoro-4-methylbenzamide 400 (M + H)
2718 N-[cis-4-( {[4-(dimethy]amino)-5-methyIpyrimidin-2-
yl]amino}methyl)cyclohexyll-4-fluoro-3-methvlbenzamide 400 (M + H) 2
2719 N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}methyl)cyc]ohexyll-3-(trifluoromethyl)benzamide 436 (M + H) 3
2720 N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}methyl)cyclohexyll-4-(trifluoroniethvl)benzamide 436 (M + H) 3
2721 N-[cis-4-( {[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}methyl)cyclohexvll-3-(trifluoromethoxy)benzamide 452 (M + H) 3
2722 N-[cis-4-( {[4-(dimethy lamino)-5-methylpyrimidin-2-
yl]amino}methyl)cyclohexvIl-4-ftrifluoromethoxy)benzamide 452 (M + H) 3
2723 4-cyano-N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino)methyl)cyclohexyl]benzamide 393 (M + H)
2724 4-bromo-N-[cis-4-( {[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}methyl)cyclohexyl]benzamide 446 (M + H) 3
2725 4-bromo-N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin'2-
yllamino}methyl)cyclohexvI]-3-methylbenzamide 460 (M + H) 2
2726 3-chloro-N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}methyI)cyC1-5hexyll-4-fluorobenzamide 420 (M + H) 2
2727 N-[cis-4-( {[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}methyl)cyclohexyl]-3-fluoro-4-(trifluoromethyl)-
benzamide 454 (M + H) 3
2728 '3,5-dichIoro-N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-
2-yi]amino}methyI)cyC1-5hexyllbenzamide 436 (M + H) 2
2729 3,4-dichloro-N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}methyl)cyclohexyl1benzamide 436 (M + H) 3
2730 N-[cis-4-( {[4-(dimethy lamino)-5-methylpyrimidin-2-
yl]amino}methyl)cyclohexyl]-2,2-difluoro-l,3-benzodioxole-5-
carboxamide 448 (M + H) ">
2731 N-[cis-4'({[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}methyl)cyC1-5hexvn-3,5-bis(trifluoromethyl)benzamide 504 (M + H) 2
2732 N-[cis-4-({[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}methyl)cyclohexyllbenzamide 368 (M + H) i
2733 N-[cis-4-( {[4-(dimethy lamino)-6-methy lpyrimidin-2-
yllamino)methyl)cyC1-5hexvl1-4-methylbenzamide 382 (M + H)
2734 N-[cis-4-({[4-(dimethyiamino)-6-methyIpyrimidin-2-
yllamino}methyl)cyclohexyll-3,4-difluorobenzamide 404 (M + H) 3
2735 N-[cis-4-({[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}methyl)cyC1-5hexyIl-4-methoxybenzamide 398 (M + H) 3

598

Ex. No. compound name MS class
2736 N-[cis-4-({[4-(dimethylamino)-6-methyIpyrimidin-2-
vnamino}methyI)cyclohexyl]-3,5-dimethoxybenzamide 428 (M + H)
2737 N-[cis-4-({[4-(dimethylamino)-6-methylpyrimidin-2-
yIlamino}methyl)cyclohexyn-3-fluoro-4-methy]benzamide 400 (M + H) *■>
2738 N-[cis-4-{ {[4-(dimethylamino)-6-methylpyrimidm-2-
yllamino}methvl)cyC1-5hexylV4-fluoro-3-methylbenzamide 400 (M + H) 3
2739 N-[cis-4-({[4-(dimethylamino)-6-methylpyrimidin-2-
yflamino}methyI)cyC1-5hexyl]-3-(trifluoromethyl)benzamide 436 (M + H)
2740 N-[cis-4-({[4-(dimethylamino)-6-methylpyrimidin-2-
yIlamino}methyl)cyC1-5hexvll-4-(trifluoromethvl)benzamide 436 (M + H)
2741 N-[cis-4-({[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}methyl)cyclohexyll-3-(trifIuoromethoxv)benzamide 452 (M + H) 3
2742 N-[cis-4-({[4-(dimethylamino)-6-methylpyrimidin-2-
vllamino}methyl)cyC1-5hexyI]-4-(trifluoromethoxv)benzamide 452 (M + H) ->
2743 4-cyano-N-[cis-4-({[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}methyl)cyclohexyl]benzamide 393 (M + H) 3
2744 4-bromo-N-[cis-4-( {[4-(dimethyIamino)-6-methylpyrimidin-2-
yl]amino)methyl)cvclohexyl]benzamide 446 (M + H) 2
2745 4-bromo-N-[cis-4-( {[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}methyl)cyclohexyl]-3-methyIbenzamide 460 (M + H) 2
2746 3-chloro-N-[cis-4-( {[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}methy0cyclohexyll-4-fluorobenzamide 420 (M + H)
2747 N-[cis-4-( {[4-(dimethyiamino)-6-methy lpyrimidin-2-
yl]amino}methyI)cyclohexyl]-3-fluoro-4-(trifluoromethyl)-
benzamide 454 (M + H)
2748 3,5-dichloro-N-[cis-4-({[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}methyl)cyclohexyllbenzamide 436 (M + H) 2
2749 3,4-dichloro-N-[cis-4-({[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}methyl)cyclohexyllbenzamide 436 (M + H) 2
2750 N-[cis-4-({[4-(dimethylamino)-6-methy!pyrimidin'2-
yl]amino}methyl)cyclohexyl]-2,2-difluoro-l,3-benzodioxole-5-
carboxamide 448 (M + H)
2751 N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}cyclohexyl)methvllbenzamide 368 (M+H)
2752 N-[(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)methyl]-4-methylbenzarnide 382 (M + H)
2753 N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}cyclohexyl)methyIl-3,4-difluorobenzamide 404 (M + H)
2754 N-[(cis-4-{[4-(diraethylamino)-6-methyIpyrimidin-2-
yllamino}cyclohexyl)methyll-4-methoxybenzamide 398 (M + H) ">
2755 N-[fcis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)methyl]-3-fIuoro-4-methvlbenzamide 400 (M + H) 2
2756 N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yI]amino}cyC1-5hexyl)methyn-4-fluoro-3-methylbenzamide 400 (M + H) 3
2757 N-[(cis-4-{[4-(dimethyiamino)-6-methylpyrimidin-2-
yllamino}cyclohexyl)methyl]-3-(trifluoromethy])benzamide 436 (M + H) -i
2758 N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}cyC1-5hexvl)methyn-4-(trifluoromethyl)benzamide 436 (M + H) 2

599

Ex. No. compound name MS class
2759 N-[(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-
vllamino}cvclohexvl)methvl]-3-ftrifluoromethoxv)ben2amide 452 (M + H) *■>
2760 N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyC1-5hexy])methyll-4-(trifluoromethoxv)benzamide 452 (M + H) ">
2761 4-cyano-N-[(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-
yllamino}cyclohexyl)methyllbenzamide 393 (M + H)
2762 4-bromo-N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
vllamino}cyclohexyl)methyl]benzamide 446 (M + H) 1
2763 4-bromo-N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}cvclohexvl)methyl]-3-methylbenzamide 460 (M + H) 1
2764 3-chloro-N-[tcis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-
yllamino}cvclohexyI)methyll-4-fluorobenzamide 420 (M + H) 1
2765 N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)methyl]-3-fluoro-4-(trifIuoromethyl)-
benzamide 454 (M + H) 2
2766 3,5-dichloro-N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yflamino}cyC1-5hexyl)methyllbenzamide 436 (M + H) 2
2767 3,4-dichloro-N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}cyclohexy!)methyllbenzamide 436 (M + H) 2
2768 N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)methyl]-2,2-difluoro-l,3-benzodioxole-5-
carboxamide 448 (M + H)
2769 N-[(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-
yIlamino}cyclohexyI)methyllbiphenyI-4-carboxamide 444 (M + H)
2770 4-chloro-N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}cyclohexyl)methy!lbenzamide 402 (M + H) 2
2771 cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-
f( 1 R)-l -pheny lethyllcyC1-5hexanecarboxamide 382 (M + H) 2
2772 cis-4- {[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino} -N-
r(lS)-l-(4-methylphenyI)ethyIlcyC1-5hexanecarboxamide 396 (M + H) 1
2773 cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-N-
[(1 R> 1 -f 4-fIuorophenyl)ethyllcyclohexanecarboxamide 400 (M + H) 1
2774 cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-
[(lS)-l-(4-fluorophenyI)ethyl]cvclohexanecarboxamide 400 (M + H) 2
2775 cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-yl]amino}-N-
[(1R)-1 -(3-methoxvpheny Oethyllcyclohexanecarboxamide 412 (M + H) 1
2776 cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2~yl]amino}-N-
[f 1S)-1 -(3-methoxyphenyl)ethy l]cyclohexanecarboxamide 412 (M + H) 1
2777 cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-y l]amino} -N-
\( 1S)-1 -(4-methoxyphenyl)ethyl]cyclohexanecarboxamide 412 (M + H) 1
2778 cis-N-[(lR)-l-(4-chlorophenyl)ethyl]-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yllamino)cyC1-5hexanecarboxamide 416 (M + H) 1
2779 cis-N-[ 1 -(4-bromophenyI)ethyl]-4- {[4-(dimethyl am ino)-5-
methyIpyrimidin-2-yl]amino)cyC1-5hexanecarboxamide 460 (M + H) 1
2780 cis-4-{[4-(dimethyiarnino)-5-methylpyrimidin-2-yl]amino}-N-
[flR)-l-(4-nitrophenyl)ethyllcyclohexanecarboxamide 427 (M + H) 1
2781 cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2'y!]amino}-N-
r(lS)-l-(4-nitrophenyl)ethyilcyC1-5hexanecarboxamide 427 (M + H) 2

600

Ex. No. compound name MS class
2782 cis-4-{[4-tdimethy!amino)-5-methylpyrimidin-2-yl]amino}-N-
[(1 R)-l -(1 -naphthyl)ethyl]cyclohexanecarboxamide 432 (M + H) 1
2783 cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-
[(1S)-1 -(1 -naphthyl)ethyllcyclohexanecarboxamide 432 (M + H) 1
2784 cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-N-(3-
fluorophenyl)cvclohexanecarboxamide 372 (M + H) 2
2785 cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}-N-(4-
propylphenyl)cyclohexanecarboxamide 396 (M + H) 2
2786 cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-N-(4-
methoxvphenyl)cvclohexanecarboxamide 384 (M + H)
2787 cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-(3-
methoxyphenyl)cyclohexanecarboxamide 384 (M + H) 1
2788 cis-N-(3-chlorophenyl)-4-{[4-(dimethyIamino)-5-
methylpyrimidin-2-yl]amino)cyclohexanecarboxamide 388 (M + H) 1
2789 cis-N-(2-bromophenyI)-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yIlamino}cyC1-5hexanecarboxamide 432 (M + H) 3
2790 cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}-N-
r(lS,2RV2-phenylcvclopropvllcyc!ohexanecarboxamide 394 (M + H) 1
2791 cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}-N-[4-
(trifluoromethyl)phenyllcyclohexanecarboxamide 422 (M + H) 1
2792 cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-N-[2-
(methylthio)pheny!]cyclohexanecarboxamide 400 (M + H) 2
2793 N2-[cis-4-(3,4-dihydroisoquinolin-2(lH)-yicarbonyl)cyclohexyl]-
N4,N4,5-trimethvlpyrimidine-2,4-diamine 394 (M + H) ->
2794 cis-N-(4-chlorophenyl)-4-{[4-(dimethylamino)-5-
methyIpyrimidin-2-yl]amino}-N-methyIcyclohexanecarboxamide 402 (M + H)
2795 cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}-N-
!"(1 S)-l -(4-methvIphenyl')ethyncyclohexanecarboxamide 396 (M + H) 1
2796 cis-4- {[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino} -N-
fflR)-l-(3-methoxyphenyl)ethyncyclohexanecarboxamide 412 (M + H) 2
2797 cis-N-[( 1S)-1 -(4-chlorophenyl)ethyI]-4-{ [4-(dimethyl am ino)-6-
methylpyrimidin-2-yllamino}cyclohexanecarboxamide 416 (M + H) 1
2798 cis-N-benzy 1-4- {[4-( dimethyl amino)-6-methylpyri mid in-2-
yf~|amino}cyclohexanecarboxamide 368 (M + H) 2
2799 cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yI]amino}-N-(4-
fluorobenzyi)cyclohexanecarboxamide 386 (M + H) 2
2800 cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}-N-(2-
fl uoroben zy l)cyc I ohexanecarboxamide 386 (M + H) 2
2801 cis-N-(3,4-difluorobenzyi)-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yllamino}cyclohexanecarboxamide 404 (M + H) 1
2802 cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-
T( 1 S)-l -(4-methoxyphenyl)ethvllcyC1-5hexanecarboxamide 412 (M + H) 1
2803 cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-
f(lS)-l-(3-methoxyphenyl)ethyl]cyclohexanecarboxamide 412 (M + H) 1
2804 cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}-N-
[(lR)-l-(4-fIuorophenyl)ethvI]cyclohexanecarboxamide 400 (M + H) 2
2805 cis-N-[(lR)-l-(4-chlorophenyI)ethyi]-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yllamino)cyclohexanecarboxamide 416 (M + H) 1

601

Ex. No. compound name MS class
2806 cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-(3-
iodobenryl)cYclohexanecarboxamide 494 (M + H) 1
2807 cis-N-(2,4-dichlorobenzyI)-4-{[4-(dimethylamino)-6-
methylpvrimidin-2-ynamino)cvC1-5hexanecarboxamide 436 (M + H) 1
2808 cis-N-(2,5-dichlorobenzyI)-4-{[4-(dimethylamino)-6-
methylpvrimidin-2-yIlamino}cyclohexanecarboxamide 436 (M + H) 1
2809 cis-4- {[4-(dimethy lamino)-6-methylpyrimidin-2-y ljamino} -N-(4-
methylbenzyl)cyclohexanecarboxamide 382 (M + H) 1
2810 cis-N-(3,5-dichlorobenzyl)-4-{[4-(dtmethyIamino)-6-
methylpyrimidin-2-yllamino}cyclohexanecarboxamide 436 (M + H) 1
2811 cis-N-(3,5-dimethoxybenzyI)-4-{[4-(dimethylamino)-6-
methylpvrimidin-2-yl]amino}cvclohexanecarboxamide 428 (M + H) 1
2812 cis-N-(3-chlorobenzyl)-4-{[4-(dimethyIamino)-6-
methylpyrimidin-2-vllamino}cyclohexanecarboxamide 402 (M + H) 1
2813 cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}-N-[3-
(trifluoromethyl)benzyllcyclohexanecarboxamide 436 (M + H) 2
2814 cis-N-[3,5-bis(trifluoromethyl)benzyl]-4-{[4-(dimethylamino)-6-
methyIpyrimidin-2-yllamino}cyclohexanecarboxamide 504 (M + H) 1
2815 cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-(3-
methoxybenzvDcyC1-5hexanecarboxamide 398 (M + H) 1
2816 cis-N-(4-chlorobenzyl)-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yllamino}cyC1-5hexanecarboxamide 402 (M + H) 1
2817 cis-N-(3,4-dichIorobenzyI)-4- {[4-(dimethylamino)-6-
methyIpyrimidin-2-yllamino}cyclohexanecarboxamide 436 (M + H) 1
2818 cis-N-(2,4-dif!uorobenzyl)-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yllamino}cyclohexanecarboxamide 404 (M + H) 1
2819 cis-N-(2,5-difluorobenzyl)-4- {[4-(dimethylamino)-6-
methylpvrimidin-2-yllamino}cyclohexanecarboxamide 404 (M + H) 1
2820 cis-N-(2,3-difluorobenzyl)-4- {[4-(dimethylamino)-6-
methylpyrimidin-2-vllamino}cyclohexanecarboxamide 404 (M + H) 1
2821 cis-N-(4-bromo-2-fluoroben2yl)^-{[4-(dimethylamino)-6-
methylpyrimidin-2-yllamino}cyclohexanecarboxamide 464 (M + H) 1
2822 cis-4-{[4-(dtmethylamino)-6-methylpyrimidin-2-yl]amino}-N-t3-
methylbenzyl)cyclohexanecarboxamide 382 (M + H) 1
2823 cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}-N-[2-
(trifluoromethoxy)benzyllcyclohexanecarboxamide 452 (M + H) 1
2824 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yI]amino)cyclohexyl)-3-methoxybenzamide 398 (M + H) 1
2825 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino)cyclohexyl)-2,6-dihydroxyisonicotinamide 401 (M + H) -i
2826 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yllamino)cyC1-5hexyI)pyrazine-2-carboxamide 370 (M + H) 3
2827 N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyritnidin-2-
yllaminoicyclohexyI)-6-hydroxynicotinamide 385 (M + H) J
2828 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yllamino}cyclohexyl)-5-methylisoxazole-3-carboxamide 373 (M + H) 2
2829 2-(3,5-difluorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6-
dimethylpyrimidin-2-yllamino}cyclohexyl)-2-hvdroxyacetamide 434 (M + H) 2

602

Ex. No. compound name MS class
2830 N-tcis-4-{[4-(dimethyIamino)-5,6-dimethy]pyrimidin-2-
yllamino)cvclohexvI)-2-methyl-l,3-oxazole-4-carboxamide 373 (M + H) 2
2831 N-(cis-4-{[4-(dimethylamino)-5,6-dimethy!pyrimidin-2-
yllamino}cyc!ohexyI)-2-methylnicotinamide 383 (M + H)
2832 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino)cvclohexyI)-2.6-dimethoxvnicotinamide 429 (M + H) 1
2833 3-amino-N-(cis-4-{[4-(dimethylamino)-5,6-dimethy]pyrimidin-2-
yl]amino}cyclohexyl)pyrazine-2-carboxamide 385 (M + H) 2
2834 N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-
yl]amino)cyclohexylV2-ethoxvnicotinamide 413 (M + H) -i
2835 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yllamino}cyclohexvl)pyridine-2-carboxamide 369 (M + H) -i
2836 3-cyano-N-(cis-4-{[4-(dimethyIammo)-5,6-dimethylpyrimidin-2-
vllamino}cyclohexyl)benzamide 393 (M + H) 1
2837 N-(cis-4- {[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yllamino}cyC1-5hexyI)-3-methvlbenzamide 382 (M + H) 1
2838 3-chloro-N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-
ynaminojcyclohexvObenzamide 402 (M + H) 1
2839 3-bromo-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino}cvclohexyl)benzamide 446 (M + H) 1
2840 N-(cis-4-{[4-(dimethy]amino)-5,6-dimethylpyrirnidin-2-
vl]amino}cvclohexylV3,5-dimethoxybenzamide 428 (M + H) 1
2841 N-(cis-4-{[4-(dimethylamino)-5,6-dimethyIpyrimidin-2-
yl]amino}cvclohexy!)-3,5-bis(trifluoromethyl)benzamide 504 (M + H) 1
2842 3,4-dichloro-N-(cis-4-{[4-(dimethylamino)-5,6-
dimethylpyrimidin-2-yllamino}cyclohexyl)benzamide 436 (M + H) 1
2843 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yllamino)cyclohexyI)-4-(trifIuoromethoxy)benzamide 452 (M + H) 2
2844 4-cyano-N-(cis-4- {[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yllamino}cyclohexyl)benzamide 393 (M + H) 1
2845 N-(cis-4- {^-(dimethylamino^S^-dimethylpyrimidin^-
ynamino}cvclohexyl)-4-methylben2amide 382 (M + H) 1
2846 N-(cis-4- {[4-(dimethylamino)-5,6-dimethyIpyrimidin'2-
ynamino}cyclohexvlV4-fIuorobenzamide 386 (M + H) 1
2847 4-chloro-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
vllamino}cyclohexvl)benzamide 402 (M + H) 1
2848 N-(cis-4- {[4-(dimethylamino)-5,6-dimethyIpyrirnidin-2-
yllamino}cyclohexyl)-2-methoxybenzamide 398 (M + H) 2
2849 4-brorao-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
vllamino)cyclohexyl)benzamide 446 (M + H) 1
2850 N-(cis-4-{[4-{dimethylamino)-5,6-dimethylpyrimidin-2-
yllamino)cyclohexyI)-4-(trifluoromethyl)benzamide 436 (M + H) 1
2851 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yllamino)cyclohexyI)-4-ethoxybenzamide 412 (M + H) i
2852 4-bromo-N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-
yllamino)cyclohexyI)-3-methylbenzamide 460 (M + H) 1
2853 N-(cis-4- {[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino}cyclohexyI)-3-fluoro-4-methyIbenzamide 400 (M + H) 1

6o:

Ex. No. compound name MS class
2854 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrim)din-2-
yllamino}cyclohexyl)-4-f]uoro--3-methylbenzamide 400 (M + H) 1
2855 N-tcis-4-{[4-(dimethylamino)-5,6-dimethyIpyrimidin-2-
yilamino}cyclohexyl)-3-ethylbenzamide 396 (M + H) 2
2856 N-{cis-4-{[4-(dimethy]amino)-5,6-dimethylpyrimidin-2-
yllamino)cvclohexyl)-3-(trifIuorornethoxy)benzamide 452 (M + H) 1
2857 5-bromo-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
vllamino}cyclohexvl)nicotinamide 447 (M + H) 1
2858 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino)cyclohexyl)-5-methvlthiophene-2-carboxamide 388 (M + H) 1
2859 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino}cyclohexyl)-6-(trifluoromethyl)nicotinamide 437 (M + H) 2
2860 N-(cis-4-{[4-(dimethylamino)-5,6-dimethyIpyrimidin-2-
vllamino}cyC1-5hexyI)-3,5-diethoxvbenzamide 456 (M + H) 1
2861 N-(cis-4- {[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-
yIlamino)cyclohexyl)-3-ethoxybenzamide 412 (M + H) 1
2862 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yllamino}cyclohexyl)-3-isopropoxybenzamide 426 (M + H) 1
2863 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yllamino}cyclohexyl)-6-hydroxypvridine-2-carboxamide 385 (M + H)
2864 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yllamino}cyclohexyl)-3,4-difluorobenzamide 404 (M + H) 1
2865 N4,N4,5,6-tetramethyl-N2-(cis-4-{[3-
(trifluororaethoxy)benzyl]amino}cyclohexyl)pyrimidine-
2,4-diamine 438 (M + H) *>
2866 N2-{cis-4-[(3,4-difluorobenzyl)amino]cyclohexyl}-N4,N4,5,6-
tetramethylpyrimidine-2,4-diamine 390 (M + H) 2
2867 N-(3,4-dimethoxyphenyI)-N'-(cis-4-{[4-(dimethyIamino)-5,6-
dimethylpyrimidin-2-yllamino)cyclohexyl)urea 433 (M + H) 1
2868 N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
ynamino}cyclohexyl)-N'-(2-ethoxyphenyl)urea 427 (M + H) 1
2869 N-[4-tbenzyIoxy)phenyl]-N'-(cis-4-{[4-(dimethylamino)-5,6-
dimethylpyrimidin-2-ynamino}cyclohexyl)urea 489 (M + H) 3
2870 1 -(4-chlorophenyl)-N-(cis-4- {[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)-
cy c lo propan ec arboxam ide 428 (M + H) 1
2871 l-(2,4-dichlorophenyI)-N-(cis-4-{[4-(diraethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)-
cy c lop ropan ecarboxam i d e 462 (M + H) 1
2872 2-(4-chIorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yllamino}cyC1-5hexy0acetamide 402 (M + H) 1
2873 N-(c i s-4- {[4-( d i methy lam i no)- 5 -methy Ipy rim i d i n-2 -
yl]amino}cyclohexyl)-l-(4-methylphenyl)-
cy c loprop an ecarboxam ide 408 (M + H) 1
2874 2-(4-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-y]lamino}cyclohexyl)propanamide 416 (M + H) 1

604

Ex. No. compound name MS class
2875 N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-
yI]amino}cyclohexyl)-l-(4-methoxyphenyl)-
cyclopropanecarboxamide 424 (M + H) 1
2876 2-(4-chlorophenyl)-N-(cis-4- {[4-(dimethylamino)-5-
methyIpyrimidin-2-yllamino}cyC1-5hexyiy2-hydroxyacetamide 418 (M + H) 1
2877 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl1amino}cyclohexyI)-2-(3-methoxvphenoxy)acetamide 414 (M + H) 1
2878 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyl)-2-f3-(trifluoromethyl)phenoxylacetamide 452 (M + H) 1
2879 2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)acetamide 418 (M + H) 1
2880 N-(cis-4- {[4-(dimethylamino)-5-methy lpyrimidin-2-
yl]amino} cyclohexy I)-2- {[2-(trifluoromethyl)pheny 1]-
sulfinvH acetamide 484 (M + H) 1
2881 2-[(2-chlorophenyl)sulfinyl]-N-(cis-4-{[4-(dimethylamino)-5-
methyipyrimidin-2-yllamino)cyclohexyi)acetamide 450 (M + H) 1
2882 2-[(3-bromophenyl)sulfmyl]-N-(cis-4-{[4-(dimethyIamino)-5-
methylpyrimidin-2-yllamino}cyC1-5hexyl)acetamide 494 (M + H) 1
2883 2-[(3,4-difluorophenyl)suIfinyl]-N-(cis-4-{[4-(dimethylamino)-5-
methvlpvrimidin^-yllaminolcyclohexyDacetamide 452 (M + H) 2
2884 2-[(3,4-difluorophenyl)sulfonyl]-N-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yI]amino}cyclohexyl)acetamide 468 (M + H)
2885 N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yilamino}cyclohexyi)-2-(3-methylphenoxy)nicotinamide 461 (M + H) 1
2886 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
vI]amino}cyclohexyl)-2-(3-fluorophenoxy)nicotinamide 465 (M + H) 1
2887 N-(cis-4-{[4-(dimethylamino)-5-methyipyrimidin-2-
yllamino}cyclohexvl)-2-(3-methoxyphenoxy)nicotinamide 477 (M + H) 1
2888 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyl)-2-(4-methoxyphenoxy)nicotinamide 477 (M + H) 1
2889 N-(cis-4- {[4-(dimethylamino)-5-methy lpyrimidin-2-
yllamino}cyclohexyl)-2-(4-iodophenoxy)nicotinamide 573 (M + H) 1
2890 N-(cis-4-{[4-(dimethy!amino)-5-methy]pyrimidin-2-
yI]amino}cyC1-5hexyl)-2-(2-methoxyphenoxv)nicotinamide 477 (M + H) 1
2891 N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
vllamino}cyC1-5hexyl}-2-(2-fluorophenoxy)nicotinamide 465 (M + H) 1
2892 2-(2-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yllamino}cyclohexy])nicotinamide 481 (M + H) 1
2893 2-(3-chlorophenoxy)~N-(cis-4-{[4-(dimethylamino)-5-
methy]pyrimidin-2-yIlamino}cyC1-5hexyl)nicotinamide 481 (M + H) 1
2894 2-(3-bromophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-
methyIpyrimidin-2-yllamino}cycloh6xyl)nicotinamide 525 (M + H) 1
2895 N-(cis-4-{[4-{dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-[3-(trifluoromethyl)phenoxy]-
nicotinamide 515(M + H) 1
2896 N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yllamino}cyclohexyl)-3-(trifluoromethyl)benzamide 422 (M + H) 1

605

Ex. No. compound name MS class
2897 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyI)-3-fluorobenzamide 372 (M + H) 1
2898 3-bromo-N-(cis-4-{[4-(dimethy]amino)-5-methyIpyrimidin-2-
yllamino}cyc!ohexyl)benzamide 432 (M + H) 1
2899 N-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyC1-5hexyl)-4-fluorobenzamide 372 (M + H) 1
2900 N-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyI)-3,5-dimethoxybenzamide 414 (M + H) 1
2901 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
vllamino}cvclohexyl)-2,4-difluorobenzamide 390 (M + H) 1
2902 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyl)-2,5-difluorobenzamide 390 (M + H) 1
2903 N-(cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)-2.3,4-trifluorobenzamide 408 (M + H) 1
2904 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyl)benzamide 354 (M + H) 2
2905 4-tert-butyl-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyl)benzamide 410 (M + H) 1
2906 4-butyl-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino)cvclohexyl)benzamide 410 (M + H)
2907 4-chloro-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
ynamino}cyclohexyl)benzamide 388 (M + H) 1
2908 3-cyano-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexvl)benzamide 379 (M + H) 1
2909 4-cyano-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide 379 (M + H) 1
2910 N-(cis-4- {[4-(dimethy lamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-methoxybenzamide 384 (M + H) ->
2911 4-bromo-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino) cyclohexvl)benzamide 432 (M + H) 1
2912 N-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-
yI]amino}cyclohexyl)-4-(trifluoromethyl)benzamide 422 (M + H) 1
2913 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyI)-4-methoxybenzamide 384 (M + H) ->
2914 2-bromo-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyl)benzamide 432 (M + H) ->
2915 2-chloro-N-(cis-4- {[4-(dimethy lamino)-5-methylpyrimidin-2-
yllamino) cyclohexyl)benzamide 388 (M + H) 3
2916 N-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-fluorobenzamide 372 (M + H) ">
2917 N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yllamino)cyclohexyI)-2-methyIbenzamide 368 (M + H)
2918 N-(cis-4- {[4-(dimethy Iamino)-5-methylpyrimidin-2-
yllamino}cyC1-5hexyl)-2-(trifluoromethyI)benzamide 422 (M + H)
2919 N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yllamino)cyclohexyl)-4-fluoro-3-(trifluoromethyl)benzamide 440 (M + H) 1
2920 4-bromo-N-(cis-4-{[4-{dimethylamino)-5-methylpyrimidin-2-
yllamino)cyC1-5hexvl)-3-methylbenzamide 446 (M + H) 1

606

Ex. No. compound name MS class
2921 N-(cis-4- {[4-(dimethy lamino)-5-methylpyrimidin-2-
yllamino}cyclohexyl)-4-ethoxybenzamide 398 (M + H) 2
2922 3-(dimethylamino)-N-(cis-4-{[4-(dimethy]amino)-5-
methylpyrimidin-2-yilamino}cyC1-5hexyI)benzamide 397 (M + H)
2923 N-(cis-4- {[4-(dimethylamino)-5-methyIpyrimidin-2-
vIlamino}cvclohexvI)-4-fluoro-3-inethvlbenzamide 386 (M + H) 1
2924 N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
vllamino}cyclohexyI)-3-fluoro-4-methylbenzamide 386 (M + H) 1
2925 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
Yllamino}cyclohexyl)-3-ethvlbenzamide 382 (M + H) 1
2926 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yI]amino}cyclohexyl)-2,2-difluoro-l,3-benzodioxo!e-5-
carboxamide 434 (M + H) 1
2927 N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yl]amino}cyC1-5hexyl)-3-ethoxybenzamide 398 (M + H) 2
2928 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexvl)-3-isopropoxybenzamide 412 (M + H) 2
2929 N-(cis-4- {[4-(dimethy lamino)-5-methyIpyrimidin-2-
yllamino}cyclohexy])-3,5-diethoxybenzamide 442 (M + H) 1
2930 N-(cis-4- {[4-(dimethylamino)-5-methyIpyrimidin-2-
yl]amino}cyclohexyl)-3-fluoro-5-(trifluoromethyl)benzamide 440 (M + H) 1
2931 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yIlamino}cyC1-5hexyl)-3-fluoro-4-(trifluoromethyl)benzamide 440 (M + H) 3
2932 3-chloro-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino)cyclohexyI)-4-fIuorobenzamide 406 (M + H) 3
2933 3,5-dibromo-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cvclohexyl)benzamide 510 (M + H) 1
2934 N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yIlamino)cyclohexyl)-3,5-dimethyIbenzamide 382 (M + H) 1
2935 4-chIoro-N-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-3-methylbenzamide 402 (M + H) 1
2936 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
y!lamino)cyclohexyl)-4-methoxy-3-ftrifluoromethyl)benzamide 452 (M + H) 1
2937 N-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl>3-methylbenzamide 368 (M + H) 1
2938 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-3-methoxybenzamide 384 (M + H) 1
2939 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyl)-4-methvlbenzamide 368 (M + H) 1
2940 3-chloro-N-(cis-4'{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyllbenzamide 388 (M + H) 1
2941 N~2—(3-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yllamino}cyC1-5hexyl)-N2-methv]2lycinamide 431 (M + H) 1
2942 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-N2-methyl-N2-(3-methylphenyl)-
glycinamide 411 (M + H) 1

607

Ex. No. compound name MS class
2943 N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yl]amino}cyclohexyl)-N2-(3-fluorophenyl)-N2-
methylalycinamide 415 (M + H) 1
2944 N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-N2-(4-fluorophenyl)-N2-
methvlglycinamide 415 (M + H) 1
2945 N2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-
methyIpyrimidin-2-yI]amino}cyclohexvl)-N2-methvialvcinamide 431 (M + H) 1
2946 N2-(3,4-difluorophenyI)-N-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyC1-5hexyl)-N2-methyl£lvcinamide 433 (M + H) 1
2947 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-N2-(3-methoxyphenyl)-N2-
methylaivcinamide 427 (M + H) 1
2948 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-N2-(4-methoxyphenyl)-N2-
methylalycinamide 427 (M + H) 2
2949 2-(4-chIorophenyl)-N-(cis-4- {[4-(dimethyIamino)-6-
methylpyrimidin-2-yllamino}cyclohexyl)-2-methylpropanamide 430 (M + H) 1
2950 2-[3,5-bis(triftuoromethyl)phenyl]-N-(cis-4-{[4-(dimethylamino)-
6-methylpyrimidin-2-yllamino}cvclohexyI)acetamide 504 (M + H) 2
2951 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
y llamino) cyclohexyl)benzamide 354 (M + H) -t
2952 4-butyI-N-(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide 410 (M + H) 3
2953 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yllamtno}cyclohexyl)-3-fluorobenzamide 372 (M + H) 2
2954 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yIlamino}cyclohexyl)-3-(trifluoromethy])benzamide 422 (M + H) 1
2955 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yIlamino}cyclohexyl)-2-methoxybenzamide 384 (M + H) 3
2956 N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-
yllamino}cyclohexyl)-4-methoxybenzamide 384 (M + H) 3
2957 3-cyano-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
y llamino} cyclohexyl)benzamide 379 (M + H) 1
2958 4-cyano-N-(cis-4-{[4-(dimethyIatnino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide 379 (M + H) 1
2959 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
vIlamino}cyclohexyl)-3,5-dimethoxvbenzamide 414 (M + H) 1
2960 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}cyclohexyl)-3-fluoro-4-(trifluoromethyl)benzamide 440 (M + H) 2
2961 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino} cyclohexy l)-4-fluoro-3-(trifluoromethyl)benzamide 440 (M + H) 1
2962 N-(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-
yI]amino}cyclohexyi)-3-fluoro-5-(trifIuoromethyi)benzamide 440 (M + H) 1
2963 3-chloro-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino)cyclohexvl)-4-fluorobenzamide 406 (M + H) 1
2964 N-(cis-4- {[4-(dimethy lamino)-6-methyIpyrimidin-2-
yllamino}cyC1-5hexyI)-4-fluoro-3-methylbenzamide 386 (M + H) 1

608

Ex. No. compound name MS class
2965 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}cyclohexyl)-3-fluoro-4-methylbenzamide 386 (M + H) 1
2966 3,5-dichloro-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yllaminolcyclohexvDbenzamide 422 (M + H) 1
2967 N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-
vIlaniino}cyclohexyI)-3-ftrifIuoromethoxy)benzamide 438 (M + H) 1
2968 N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-
yI]amino}cyclohexyI)-3,5-difluorobenzamide 390 (M + H) 1
2969 4-bromo-N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-
Ynamino}cyclohexylV3-methylbenzamide 446 (M + H) 1
2970 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yi"|amino}cyclohexyl)-3-ethylbenzamide 382 (M + H) ■^
j
2971 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cvc!ohexyl)-4-ethoxvbenzamide 398 (M + H) 3
2972 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yIlamino)cvclohexyI)-4-ftrif]uoromethyl)benzamide 422 (M + H) 2
2973 4-bromo-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
ynamino}cyclohexyl)benzamide 432 (M + H) 1
2974 N-(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-
yl1amino}cyclohexyl)-4-ethylbenzamide 382 (M + H) 2
2975 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)-3,5-diethoxybenzamide 442 (M + H) 1
2976 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)-3-ethoxybenzamide 398 (M + H) 2
2977 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
ynamino}cyclohexyl)-3-isopropoxybenzamide 412 (M + H) 1
2978 5-bromo-N-(cis-4- {[4-(dimethy Iamino)-6-methylpyrimidin-2-
yllamino}cvclohexyl)nicotinamide 433 (M + H) 1
2979 5-bromo-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino) cyc!ohexyl)-2-fliramide 422 (M + H) 1
2980 5-chloro-N-(cis-4-{[4-(dimethylammo)-6-methylpyrimidin-2-
vl]amino}cyC1-5hexyI)-2-furamide 378 (M + H) 1
2981 N-(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-
vnamino)cyclohexy])-4-methoxy-3-(trifluoromethyl)benzamide 452 (M + H) 2
2982 4-chloro-N-(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-
yIlamino)cyclohexyl)-3-ftrifluoromethvI)benzamide 456 (M + H) 1
2983 N-(cis-4- {[4-(dimethy]amino)-6-methyIpyrimidin-2-
yllamino)cyclohexyl)-3-methyIbenzamide 368 (M + H) 1
2984 N-(cis-4-{[4-(dimethylamino)-6-methyipyrimidin-2-
yIlamino}cyclohexyl)-3-methoxybenzamide 384 (M + H) 1
2985 N-(cis-4-{[4-(dimethylamino)-6-methyipynmidin-2-
y!]amino)cyclohexyl)^4-methylbenzamide 368 (M + H) 1
2986 4-chIoro-N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-
yilamino}cyclohexyl)benzamide 388 (M + H) 1
2987 3-chloro-N-(cis-4-{[4-(dimethylamino)-6-methyipyrimidin-2-
v]lamino}cyclohexyl)benzamide 388 (M + H) 1
2988 N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-
yllamino} cyclohexyl)-3,4-difIuorobenzamide 390 (M + H) 1

609

Ex. No. compound name MS class
2989 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cvclohexvI)-4-(trifIuoromethoxv)benzamide 438 (M + H)
2990 N-(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyI)-4-fIuorobenzamide 372 (M + H) 1
2991 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino)cvC1-5hexvl)-3,4,5-trimethoxybenzamide 444 (M + H) 1
2992 N-(4-{[4-(dimethylamino)-6-methyIpyrimidin-2-
yl]amino}cyclohexyI)-3-nitrobenzamide 399 (M + H) 1
2993 N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-
yllamino}cyclohexyl>2.2-diphenylacetamide 444 (M + H) 1
2994 3,4-dichloro-N-(cis-4-{[4-(dimethylamino)-6-raethyIpyrimidin-2-
ynamino)cyclohexvl)benzamide 422 (M + H) 1
2995 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
ynamino)cyclohexyl)benzenesulfonamide 390 (M + H) 3
2996 N4,N4,5-trimethyl-N2-{cis-4-[(4-
methylbenzyl)amino]cyclohexyI}pyrimidine-2,4-diamine 354 (M + H) 3
2997 N2-{cis-4-[(3,4-difluorobenzyl)amino]cyclohexyI}-N4,N4,5-
trimethylpyrimidine-2,4-diamine 376 (M + H) 3
2998 N2-{cis-4-[(3-chlorobenzyl)amino]cyclohexyl}-N4,N4,5-
trimethylpyrimidine-2,4-diarnine 374 (M + H) 3
2999 N2-{cis-4-[(3-bromobenzyl)amino]cyclohexyl}-N4,N4,5-
trimethv1pyrimidine-2,4-diamine 418 (M + H) 3
3000 N2-{cis-4-[(3,5-dimethoxybenzyl)amino]cyclohexyl}-N4,N4,5-
trirnethyIpyrimidine-2,4-diamirie 400 (M + H) 2
3001 N2-{cis-4-[(3,5-dichIorobenzyl)amino]cyC1-5hexyl}-N4,N4,5-
trimethylpyrimidine-2,4-diamine 408 (M + H)
3002 N2-{cis-4-[(354-dichlorobenzyl)amino]cyclohexyl}-N4,N455-
trimethylpyrimidine-2,4-diamine 408 (M + H) 3
3003 N2-{cis-4-[(4-methoxy-3-methylbenzyI)amino]cyclohexyl}-
N4,N4,5-triniethylpyrimidine-2,4-diamine 384 (M + H)
3004 N4,N4,5-trimethyl-N2-(cis-4-{[3-
(trifluoromethoxy)benzyl]amino}cyclohexyl)pyrimidine-
2,4-diamine 424 (M + H)
3005 N4,N4,6-trimethyl-N2-(cis-4- {[3-
(trifluoromethoxy)benzyl]amino}cyclohexyl)pyrimidine-
2.4-diamine 424 (M + H) 3
3006 N-(cis-4-{[4-(dimethylamino)-5-ftrifluoromethyl)pyrimidin-2-
yl]amino}cyC1-5hexyl)-3,4-difIuorobenzamide 444 (M + H) ->
3007 N-[((lR,3S)-3-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino)cyC1-5pentyI)methyn-6-(3-fluorophenoxy)nicotinamide 465 (M + H)
3008 6-(3-chIorophenoxy)-N-[((IR,3S)-3-{[4-(dimethylamino)-5-
methylpyrimidin-2-yI]amino}cyclopentyl)methynnicotinamide 481 (M + H)
3009 N-[((lR,3S)-3-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclopentyI)methyI]-6-(3-methoxyphenoxy)-
nicotinamide 477 (M + H)
3010 N-[((lR,3S)-3-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclopentyl)methyl]-6-(2-methoxyphenoxy)-
nicotinamide 477 (M + H)

610

Ex. No. compound name MS class
3011 N-[((lR,3S)-3-{[4-(dimethy!amino)-5-methyipyrimidin-2-
vl]amino}cyclopentyl)methyIl-6-(2-fluorophenoxv)nicotinamide 465 (M + H)
3012 2-(4-bromophenoxy)-N-[((lR,3S)-3-{[4-(dimethylamino)-5-
methylpyrimidin-2-yI]amino}cyC1-5pentyl)methvl1nicotinamide 525 (M + H) 2
3013 N-[(( I R,3 S)-3- {[4-(dimethy Iamino)-5-methy lpyrimidin-2-
yl]amino}cyclopentyl)methyI]-2-(2-methoxyphenoxy)-
nicotinamide 477 (M + H) 1
3014 2-(2-bromophenoxy)-N-[({ 1 R,3 S)-3- {[4-(dimethylamino)-5-
methylpyrimidin-2-yllamino}cyclopentyl)methynnicotinamide 525 (M + H)
3015 N-[((lR,3S)-3-{[4-(dimethyiamino)-5-methylpyrimidin-2-
yl]amino}cyclopentyI)methyll-2-(2-fluorophenoxy)nicotinamide 465 (M + H) 1
3016 N-[((lR,3S)-3-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclopentyl)methyl]-2-(4-methoxyphenoxy)-
nicotinamide 477 (M + H)
3017 N-[(( 1 R,3 S)-3- {[4-(dimethy lamino>5-methylpyrimidin-2-
yllamino)cyclopentyl)methyll-2-(3-fluorophenoxy)nicotinamide 465 (M + H)
3018 2-(3-chIorophenoxy)-N-[(( 1 R,3 S)-3- {[4-(dimethylamino)-5-
methyIpvrimidin-2-yllamino}cyclopentyl)methyllnicotinamide 481 (M + H)
3019 2-(3-chloro-4-fluorophenoxy)-N-[((lR,3S)-3-{[4-
(dimethylamino)-5-methylpyrimidin-2-
yllamino)cyclopentvl)methyl]-nicotinamide 499 (M + H) 2
3020 2-(4-chloro-3-fluorophenoxy)-N-[((lR,3S)-3-{[4-
(dimethyIamino)-5-methyipyrimidin-2-
yilamino}cyclopentyl)methyl]-nicotinamide 499 (M + H) 3
3021 N-(3-chlorophenyI)-N'-(cis-4- {[4-(dimethylamino)-5-
methylpyrimidin-2-yllamino}cyclohexyl>N-methylurea 417 (M + H) 1
3022 N-(3,4-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-
methyIpyrimidin-2-yl]amino}cvclohexyl)-N-methylurea 451 (M + H) 1
3023 N'-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)-N-methyl-N-(3-methylphenvl)urea 397 (M + H) 1
3024 N'-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexy!)-N-methyl-N-(4-methylphenyl)urea 397 (M + H) 1
3025 N'-(cis-4- {[4-(dimethy lamino)-5-methylpyrimidin-2-
yI]amino}cyclohexyI)-N-(3-fluorophenyI)-N-methvlurea 401 (M + H) 1
3026 N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyC1-5hexyl)-N-(4-fluorophenyl)-N-methylurea 401 (M + H) 1
3027 N-(4-chIorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino)cyclohexyl)-N-methylurea 417 (M + H) 1
3028 N'-(cis-4-{[4-(dimethylamino)-5-niethylpyrimidin-2-
yl]amino}cyclohexyl)-N-(3-methoxyphenvl)-N-methykirea 413 (M + H) 1
3029 N'-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-
yI]amino)cyclohexyI)-N-(4-methoxyphenyl)-N-methylurea 413 (M + H) 1
3030 3,4-dichloro-N-(cis-4-{[5-metbyl-4-(methyIamino)pyriraidin-2-
yl]amino}cyclohexyl)benzamide 408 (M + H) 3

611
Example 3031
3,4-Difluoro-7V-[cw-4-(quinoHn-2-ylamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of (c/s-4-benzyloxycarbonylamino~cyC1-5hexyl)-carbamic acid benzyl ester.
To a suspension ofczs-cyclohexane-l,4-dicarboxylic acid (25.0 g, 145 mmol) in benzene (125
mL) were added phosphorazidic acid diphenyl ester (81.9 g, 298 mmol) and triethylamine (30.1 g, 297
mmol). The reaction mixture was stirred at reflux for 2.5 hr. Benzyl alcohol (32.2 g, 298 mmol) was
added and the mixture was stirred at reflux for 24 hr. The reaction mixture was concentrated and the
residue was dissolved in EtOAc and H2O. The organic layer was separated and the aqueous layer was
extracted with EtOAc (twice). The combined organic layer was washed with 1 M aqueous KHSO4,
saturated aqueous NaHCO3, and brine, dried over MgSO4, filtered, concentrated, and purified by flash
chromatography (silica gel, 33% EtOAc in hexane) to give (c/s-4-benzyloxycarbonylamino-
cyclohexyl)-carbamic acid benzyl ester (52.0 g, 94%) as a colorless oil.
ESI MS m/e 405, M + Na+; ]H NMR (300 MHz, CDC13) 8 7.15-7.40 (m, 10 H), 5.07 (s, 4 H),
4.70-5.00 (m, 2 H), 3.52-3.80 (m, 2 H), 1.60-1.80 (m, 4 H), 1.45-1.60 (m, 4 H).
Step B: Synthesis of (ctf-4-amino-cyclohexyl)-carbamic acid tert-butyl ester.
To a solution of (c«-4-benzyloxycarbonylamino-cyclohexyl)-carbamic acid benzyl ester
(91.7 g, 240 mmol) in MeOH (460 mL) was added 5% Pd/C (9.17 g). The reaction mixture was
stirred at ambient temperature under hydrogen atmosphere for 2.5 days, filtered through a pad of celite,
and concentrated to give a diamine as a colorless oil. To a solution of the diamine in MeOH (550 mL)
was added a solution of (Boc)2O (6.59 g, 30.2 mmol) in MeOH (80 mL) dropwise over 4 hr. The
reaction mixture was stirred at ambient temperature for 1.5 days and concentrated. After dissolution
with H2O, the aqueous layer was extracted with CHC13 (three times). The combined organic layer was
dried over MgSO4, filtered, and concentrated to give c/s-(4-amino-cyclohexyl)-carbamic acid
ter/-butyl ester (7.78 g, 15%, crude) as a colorless oil. The aqueous layer was concentrated and the
residue was dissolved in MeOH, dried over MgSO4, filtered, and concentrated to give a recovered
diamine (32.9 g) as a colorless oil. To a solution of the recovered diamine (32.9 g, 288 mmol) in

612
MeOH (660 mL) was added a solution of (Boc)2O (6.29 g, 28.8 mmol) in MeOH (80 mL) dropwise
over 5 hr. The reaction mixture was stirred at ambient temperature for 10 hr and concentrated. After
dissolution with H2O, the aqueous layer was extracted with CHCI3 (three times). The combined
organic layer was dried over MgSO4, filtered, and concentrated to give
cw-(4-amino-cyclohexyl)-carbamic acid tert-buty\ ester (8.16 g, 16%, crude) as a colorless oil. The
aqueous layer was concentrated and the residue was dissolved in MeOH, dried over MgSO4, filtered,
and concentrated to give a recovered diamine (23.1 g) as a colorless oil. To a solution of the recovered
diamine (23.1 g, 202 mmol) in MeOH (462 mL) was added a solution of (Boc)20 (4.42 g, 20.3 mmol)
in MeOH (56 mL) dropwise over 4 hr. The reaction mixture was stirred at ambient temperature for
3.5 days and concentrated. After dissolution with H2O, the aqueous layer was extracted with CHC13
(three times). The combined organic layer was dried over MgSO4, filtered, and concentrated to give
c/5-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester (5.01 g, 10% based on starting material) as a
colorless oil. The aqueous layer was concentrated and the residue was dissolved in MeOH, dried over
MgSO4, filtered, and concentrated to give a recovered diamine (16.0 g) as a colorless oil. To a
solution of the recovered diamine (16.0 g, 140 mmol) in MeOH (320 mL) was added a solution of
(Boc)2O (3.06 g, 14.0 mmol) in MeOH (40 mL) dropwise over 4 hr. The reaction mixture was stirred
at ambient temperature for 13 hr and concentrated. After dissolution with H2O, the aqueous layer was
extracted with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtered, and
concentrated to give c/s-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester (3.53 g, 7% based on the
starting material) as a colorless oil. The aqueous layer was concentrated and the residue was dissolved
in MeOH, dried over MgSO4, filtered, and concentrated to give a recovered diamine (11.1 g) as a
colorless oil.
ESI MS m/e 215, M + H+; *HNMR (300 MHz, CDC13) 5 4.30-4.82 (m, 1 H), 3.50-3.80 (m, 1 H),
2.78-2.95 (m, 1 H), 1.44 (s, 9H), 1.20-1.80 (m, 8 H).
Step C: Synthesis of (as-4-{[l-(3,4-dinuoro-phenyl)-methanoyl]-amino}-cyclohexyl)-
carbamic acid tert-butyl ester.
To a solution of 3,4-difluoro-benzoic acid (4.10 g, 25.9 mmol) and (cw-4-amino-cyC1-5hexyl)-

61:
carbamic acid tert-bnty\ ester (5.05 g, 23.6 mmol) in DMF (50 mL) were added Et3N (90 mL, 56.7
mmol), HOBt-H2O (5.41 g, 35.3 mmol), and EDC-HCI (4.97 g, 25.9 mmol). The reaction mixture
was stirred at ambient temperature for 17 hr. To the reaction mixture was added water (200 mL) and
the suspension was stirred at ambient temperature for 10 min. The precipitated was collected by
filtration, washed with H2O and EtOH, and dried at 80 °C under reduced pressure to give (cis-4-
{[l-(3,4-difIuoro-phenyl)-methanoyI]-amino}-cyC1-5hexyl)-carbamic acid tert-buty\ ester (5.20 g,
62.3%) as a white solid.
ESI MS m/e 377, M + Na+;'HNMR (300 MHz, CDCI3) 5 1.45 (s, 9 H), 1.53-1.95 (m, 8 H), 3.60-3.74
(m, 1 H), 4.00-4.16 (m, 1 H), 4.50-4.68 (m, 1 H), 5.95-6.09 (m, 1 H), 7.15-7.28 (m, 1 H), 7.43-7.68
(m, 2 H).
Step D: Synthesis of W-(cis-4-amino-cyclohexyl)-3,4-difluoro-benzamide.
A solution of (cw-4-{[l-(3,4-difluoro-phenyl)-methanoyl]-amino}-cyclohexyI)-
carbamic acid terf-butyl ester (5.20 g, 14.7 mmol) in EtOAc (52 mL) was cooled on an ice-bath and
4 M hydrogen chloride in EtOAc (104 mL) was added. The mixture was stirred at ambient
temperature for 1 hr and concentrated. The residue was dissolved in 1 M aqueous NaOH and the
aqueous layer was extracted with CHCI3 (three time). The combined organic layer was dried over
MgSO4, filtered, concentrated, and dried at 60 °C under reduced pressure to give N-(cis-4-am'mo-
cyclohexyi)-3,4-difluoro-benzamide (3.00 g, 80%) as a white solid.
ESI MS m/e 255, M + H+ ; ]H NMR (300 MHz, CDC13) 8 1.15-1.52 (m, 3 H), 1.59-1.89 (m, 5 H),
2.94-3.06 (m, 1 H), 4.06-4.20 (m, 1 H), 6.01-6.18 (m, 1 H), 7.13-7.26 (m, 1 H), 7.43-7.50 (m, 1 H),
7.57-7.67 (m, 1 H).
Step E: Synthesis of S^-difluoro-A^cw^-tquinoIin^-ylaminoJ-cyclohexylJ-benzamide
hydrochloride.
A mixture of 2-chloro-quinoline (200 mg, 1.22 mmol) and N-{cis~4-amino-
cyclohexyl)-3,4-difluoro-benzamide (342 mg, 1.34 mmol) in butanol (1 mL) was stirred at 130 °C for

614
60 hr in a sealed tube. The reaction mixture was poured into saturated aqueous NaHCO3 and the
aqueous layer was extracted with CHCI3 (three times). The combined organic layer was dried over
MgSO4, filtered, concentrated, and purified by medium-pressure liquid chromatography (NH-silica
gel, 20% to 50% EtOAc in hexane). To a solution of the above material in EtOAc (2 mL) was added
4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 1 hr
and concentrated. The residue was suspended in Et2O (20 mL) and the suspension was stirred at
ambient temperature for 2 hr. The precipitate was filtered, washed with Et2O, and dried at 80 °C under
reduced pressure to give 3,4-difluoro-Ar-[c/5-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide
hydrochloride (189 mg, 37%) as a white solid.
ESI MS m/e 382, M (free) + H+ ; 'H NMR (300 MHz, CDCI3) 5 1.80-2.09 (m, 8 H), 3.96-4.24 (m, 2
H), 6.90-7.03 (m, 2 H), 7.14-7.25 (m, 1 H), 7.41-7.48 (m, 1 H), 7.57-7.64 (m, 1 H), 7.69-7.79 (m, 4
H),8.18(d,y=9.6Hz, 1 H), 9.73-9.76 (m, 1 H).
Example 3032
2-Phenoxy-A^c/s-4-(quinolin-2-ylamino)-cyC1-5hexyl]-nicotinaniide hydrochloride
Step A: Synthesis of jV-(c/s-4-amino-cyclohexyl)-2-phenoxy-nicotinamide.
To a solution of (c/s-4-amino-cyC1-5hexyi)-carbamic acid tert-buty\ ester obtained in step B of
1 example 3031 (6.00 g, 27.8 mmol) in CHC13 (60 mL) was added ;-Pr2NEt (9.67 mL, 55.6 mmol). The
mixture was cooled on an ice-bath and 2-phenoxy-nicotinoyl chloride (6.50 g, 27.8 mmol) was added.
The mixture was stirred at ambient temperature for 17 hr. The reaction was quenched with saturated
aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (three times). The combined
organic layer was dried over MgSO,*, filtered, and concentrated. To a solution of the above material
> in EtOAc (100 mL) and CHCI3 (40 mL) was added 4 M hydrogen chloride in EtOAc (100 mL). The
mixture was stirred at ambient temperature for 1 hr and concentrated. The residue was dissolved in
1 M aqueous NaOH and the aqueous layer was extracted with CHC13 (three time). The combined
organic layer was dried over MgSO^ filtered, concentrated, and purified by medium-pressure liquid

615
chromatography (NH-silica gel, 0.2% to 1% MeOH in CHCI3) to give Ar-(c/5-4-amino-cyclohexyl)-
2-phenoxy-nicotinamide (3.51 g, 41%) as a pale yellow oil.
ESI MS m/e 312, M + H+ ; 'H NMR (300 MHz, CDCI3) 5 1.12-1.39 (m, 3 H), 1.65-1.94 (m, 5 H),
2.80-2.91 (m, 1 H), 4.18-4.30 (m, 1 H), 7.13-7.22 (m, 3 H), 7.25-7.33 (m, 1 H), 7.41-7.51 (m, 2 H),
8.04-8.14 (m, 1 H), 8.22 (dd, 7=4.7, 2.1 Hz, 1 H), 8.62 (dd, J= 7.6, 2.0 Hz, 1 H).
Step B: Synthesis of 2-phenoxy-Ar-[m-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide
hydrochloride.
A mixture of 2-chloro-quinoline (200 mg, 1.22 mmol) and cis-N-(4-am\no-
cyclohexyi)-2-phenoxy-nicotinamide(418mg, 1.34 mmol) in butanol (1 mL) was stirred at 130 °C for
6 days in a sealed tube. The reaction mixture was poured into saturated aqueous NaHCO3 and the
aqueous layer was extracted with CHCI3 (three times). The combined organic layer was dried over
MgSOd, filtered, concentrated, and purified by medium-pressure liquid chromatography (NH-silica
gel, 10% to 16% EtOAc in hexane). To a solution of the above material in EtOAc (10 mL) was added
4 M hydrogen chloride in EtOAc (0.2 mL). The mixture was stirred at ambient temperature for 1 hr,
and concentrated. The residue was suspended in Et2O (20 mL) and the suspension was stirred at
ambient temperature for 2 hr. The precipitate was collected by filtration, washed with Et2O, and dried
at 60 °C under reduced pressure to give 2-phenoxy-/V-[ci.s-4-(quinolin-2-ylamino)-
cyclohexyl]-nicotinamide hydrochloride (138 mg, 37%) as a white solid.
ESJ MS m/e 461, M (free) + Na+ ; ]H NMR (300 MHz, CDC13) 5 1.87-2.10 (m, 8 H), 3.83-3.97 (m,
1 H) 4.12-4.24 (m, 1 H), 6.90 (d, J= 9.5 Hz, 1 H), 7.12 (dd, J= 7.6, 4.5 Hz, 1 H), 7.20-7.32 (m, 3 H),
7.37-7.50 (m, 3 H), 7.66-7.80 (m, 3 H), 7.95 (d, J= 7.0 Hz, 1 H) 8.13 (d, J= 9.6 Hz, 1 H), 8.21 (dd,
J= 4.6, 2.2 Hz, 1 H), 8.53 (dd, J= 7.6, 1.9 Hz, I H), 9.77-9.92 (m, 1 H).
Example 3033
S-Methyl-yV-fcw^-fquinolin^-ylamino^cyclohexyll-benzamide hydrochloride

616
Step A: Synthesis of c/s-A^quinoIin-Z-yl-cyclohexane-M-diamine.
A mixture of 2-chloro-quinoline (16.0 g, 97.8 mol) and (m-4-amino-cyclohexyI)-carbamic
acid tert-buty\ ester obtained in step B of example 3031 (23.0 g, 107.5 mol) in butanol (16 mL) was
stirred at 130 °C for 3 days. The reaction mixture was poured into saturated aqueous NaHCO3 and the
aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over
MgSO4, filtered, concentrated, and purified by medium-pressure liquid chromatography (NH-silica
gel, 10% EtOAc in hexane) to give a pale yellow oil. To a solution of the above material in EtOAc
(160 mL) was added 4 M hydrogen chloride in EtOAc (80 mL). The mixture was stirred at ambient
temperature for 12 hr and concentrated. The residue was dissolved in 1 M aqueous NaOH and the
aqueous layer was extracted with CHC13 (three time). The combined organic layer was dried over
MgSO4, filtered, and purified by medium-pressure liquid chromatography (NH-silica gel, 2% to 5%
MeOH in CHC13) to give c^-7*/-quinolin-2-yl-cyclohexane-l,4-diamine (6.30 g, 27%) as pale yellow
solid.
ESI MS m/e 242, M + H+; ]HNMR (300 MHz, CDC13) 5 1.12-1.53 (m, 4 H), 1.65-1.93 (m, 6 H),
2.84-2.98 (m, 1 H), 4.04-4.16 (m, 1 H), 4.78-4.91 (m, 1 H), 6.61 (d,J=9.0Hz, 1 H), 7.17 (ddd, J =
8.05 6.9, 1.2 Hz, 1 H), 7.46-7.58 (m, 2 H), 7.61-7.66 (m, 1 H), 7.79 (d, J= 8.9 Hz, 1 H).
Step B: Synthesis of 3-methyl-JV-[m-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide
hydrochloride.
To a solution ofc/s-JV-quinoIin-2-yl-cyclohexane-l,4-diarnine (300 mg, 1.24 mmol) in CHC13
(2 mL) were added /-Pr2NEt (0.45 mL, 2.60 mmol) and 3-methyl-benzoyl chloride (210 mg, 1.36
mmol) in CHC13 (1 mL). The mixture was stirred at ambient temperature for 17 hr. The reaction was
quenched with saturated aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (three
times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica gel, 20% EtOAc in hexane) to give a colorless oil.
To a solution of the above material in EtOAc (10 mL) was added 4 M hydrogen chloride in EtOAc
(0.2 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated. The residue was
suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature for 2 hr. The

617
precipitate was collected by filtration, washed with Et2O, and dried at 60 °C under reduced pressure to
give 3-methyl-AL[cw-4-(quinoIin-2-ylamino)-cyC1-5hexyI]-benzamide hydrochloride (294 mg, 60%)
as a white solid.
ESI MS m/e 382, M (free) + Na+ ; 'H NMR (300 MHz, CDC13) 5 1.82-2.07 (m, 8 H), 2.40 (s, 3 H),
3.93-4.04 (m, 1 H), 4.08-4.26 (m, 1 H), 6.49-6.58 (m, 1 H), 6.94 (d, J= 9.5 Hz, 1 H), 7.25-7.32 (m,
2 H), 7.40-7.48 (m, 1 H), 7.56-7.66 (m, 2 H), 7.67-7.81 (m, 3 H) 8.17 (d, J= 9.5 Hz, 1 H), 9.74-9.87
(m, 1 H).
Example 3034
3-Methoxy-Ar-[m-4-(quinolin-2-yIamino)-cyC1-5hexyl]-benzamide hydrochloride
Step A: Synthesis of 3-methoxy-A^c«-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide
hydrochloride.
Using the procedure for the step B of example 3033, the title compound was obtained.
ESI MS m/e 398, M (free) + Na+ ; 'H NMR (300 MHz, CDC13) 5 1.78-2.09 (m, 8 H), 3.86 (s, 3 H),
3.94-4.06 (m, 1 H), 4.08-4.25 (m, 1 H), 6.63 (d, J= 8.6 Hz, 1 H), 6.91-7.05 (m, 2 H), 7.28-7.48 (m,
4H), 7.68-7.80 (m, 3 H), 8.17 (d,J= 9.3 Hz, I H), 9.75-9.84 (m, 1 H).
Example 3035
3-Chloro-A^-[c/y-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 3-chloro-Ar-[c/$-4-(quinolin-2-ylamino)-cyclohexyI]-benzamide
hydrochloride.
Using the procedure for the step B of example 3033, the title compound was obtained.
ESI MS m/e 402, M (free) + Na+ ; !H NMR (300 MHz, CDC13) 5 1.82-2.10 (ra, 8 H), 3.96-4.07 (m,
1 H), 4.09-4.26 (m, I H), 6.75 (d, J= 7.8 Hz, 1 H), 6.96 (d, J = 9.3 Hz, 1 H), 7.33-7.49 (m, 3 H),

618
7.66-7.79 (m, 4 H), 7.83-7.88 (m, 1 H), 8.19 (d, J= 9.3 Hz, 1 H), 9.80 (d, J= 8.5 Hz, I H).
Example 3036
5-Nitro-thiophene-3-carboxylic acid [cjs-4-(quinoIin-2-ylamino)-cyclohexyl]-
amide hydrochloride
Step A: Synthesis of 5-nitro-thiophene-3-carboxylic acid [c«--4-(quinolin-2-
ylamino)-cyclohexyl]-amide hydrochloride.
To a solution of 5-nitro-thiophene-3-carboxylic acid (516 mg, 2.98 mmol) and
c/5-Ar-quinoIin-2-yl-cyclohexane-l,4-diamine obtained in step A of example 3033 (600 mg, 2.48
mmol) in DMF (6 mL) were added Et3N (0.83 mL, 5.95 mmol), HOBt-H2O (570 mg, 3.72 mmol), and
EDC-HC1 (571 g, 2.98 mmol). The reaction mixture was stirred at ambient temperature for 12 hr. To
the reaction mixture was added water (20 mL) and the suspension was stirred at ambient temperature
for 30 min. The precipitated was collected by filtration, washed with H2O, and purified by
medium-pressure liquid chromatography (NH-silica gel, 33% to 50% EtOAc in hexane and silica gel,
2% to 5% MeOH in CHC13) to give a pale yellow oil. To a solution of the above material in EtOAc
(10 mL) was added 4 M hydrogen chloride in EtOAc (0.2 mL). The mixture was stirred at ambient
temperature for 1 hr and concentrated. The residue was suspended in Et2O (20 mL) and the
suspension was stirred at ambient temperature for 2 hr. The precipitate was collected by filtration,
washed with Et2O, and dried at 60 °C under reduced pressure to give 5-nitro-thiophene-3-carboxylic
acid [cw-4-(quinolin-2-ylamino)-cyclohexyl]-amide hydrochloride (329 mg, 60%) as a yellow solid.
ESI MS m/e 419, M (free) + Na+ ; !H NMR (300 MHz, CDC13) 5 1.80-2.18 (m, 8 H), 3.96-4.25 (m,
2 H), 6.97 (d, J= 9.3 Hz, 1 H), 7.39-7.53 (m, 2 H), 7.67-7.80 (m, 3 H), 8.20 (d, J= 9.4 Hz, 1 H),
8.26-8.30 (m, 1 H), 8.39-8.42 (m, I H), 9.59 (d, J= 8.6 Hz, I H).

619
Example 3037
2-Chloro-7V-[C1-5-4-(quinolin-2-ylamino)-cyC1-5hexyll-nicotinamide hydrochloride
Step A: Synthesis of 2-chloro-iV-[m-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide
hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 403, M (free) + Na+ ; lHNMR (300 MHz, CDCI3) 5 1.84-2.17 (m, 8 H), 3.93-4.05 (m,
1 H), 4.13-4.30 (m, 1 H), 6.89-7.02 (m, 2 H), 7.30-7.50 (m, 2 H), 7.67-7.81 (m, 3 H), 7.96 {d, J= 7.5
Hz, 1 H), 8.19 (d, J= 9.6 Hz, 1 H), 8.44-8.50 (m, 1 H), 9.73-9.87 (m, 1 H).
Example 3038
3-Chloro-4-fluoro-A^-[cw-4-(quinolin-2-ylamino)-cyclohexyI]-benzamide hydrochloride
Step A: Synthesis of 3-chloro-4-fluoro-7V-[ci5-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide
hydrochloride.
Using the procedure for the step B of example 3033, the title compound was obtained.
ESI MS m/e 420, M (free) + Na+ ; ]H NMR (300 MHz, CDC13) 5 1.78-2.08 (m, 8 H), 3.95-4.06 (m,
1 H), 4.07-4.23 (m, 1 H), 6.68-6.78 (m, 1 H), 6.95 (d, J= 9.6 Hz, 1 H), 7.18 (t, 7= 8.6 Hz, 1 H),
7.41-7.48 (m, 1 H), 7.68-7.79 (m, 4 H), 7.95 (dd, J= 7.0, 2.2 Hz, 1 H), 8.18 (d, J= 9.6 Hz, 1 H), 9.79
(d,/=8.4Hz, 1 H).
Example 3039
3,5-Dimethoxy--/V-[a5-4-(quinolin-2-yIamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 3,5-dimethoxy-iV-[c«-4-(quinolin-2-yIamino)-cyclohexyl]-benzamide
hydrochloride.

620
Using the procedure for the step B of example 3033, the title compound was obtained.
ESI MS m/e 428, M (free) + Na+ ; !HNMR (300 MHz, CDCI3) 5 1.80-2.14 (m, 8 H), 3.85 (s, 6 H),
3.95-4.26 (m, 2 H), 6.53-6.66 (m, 2 H), 6.89-7.01 (m, 3 H), 7.40-7.51 (m, 1 H), 7.68-7.82 (m, 3 H),
8.18 (d, 7=9.6 Hz, 1 H), 9.76-9.85 (m, 1 H).
Example 3040
3,4-Dichloro-iV-[c/s-4-(quinolin-2-y1ainino)-cyC1-5hexyll-benzamide hydrochloride
Step A: Synthesis of 3,4-dichIoro-A^c/y-4-(quinolin-2-ylamino)-cyclohexylJ-benzamide
hydrochloride.
Using the procedure for the step B of example 3033, the title compound was obtained.
ESI MS m/e 436, M(free) + Na+ ; !HNMR (300 MHz, CDCI3) 5 1.81-2.15 (m, 8 H), 3.98-4.25 (m,
2 H), 6.87-7.00 (m, 2 H), 7.42-7.52 (m, 2 H), 7.65-7.80 (m, 4 H), 7.98 (d, J= 2.0 Hz, 1 H), 8.19 (d,
J= 9.5 Hz, 1 H), 9.87 (d, J= 8.6 Hz, 1 H).
Example 3041
Benzo[2,l,3]oxadiazole-5-carboxyHc acid-[ew-4-(quinolin-2-ylamino)-cyclohexyl]-amide
hydrochloride
Step A: Synthesis of benzo[2,l,3]oxadiazoIe-5-carboxylic acid-[c/?-4-(quinolin-2-ylamino)-
cyclohexyl]-amide hydrochloride.
Using the procedure for the step B of example 3033, the title compound was obtained.
ESI MS m/e 388, M (free) + H+ ; 'HNMR (300 MHz, CDC13) 5 1.81-2.23 (m, 8 H), 3.98-4.31 (m, 2
H), 6.97 (d, J= 9.5 Hz, 1 H), 7.38-7.50 (m, 2 H), 7.70-7.78 (m, 3 H), 7.88 (ddd, J= 14.3, 9.3, 1.2 Hz,
2 H), 8.20 (d, J= 9.5 Hz, 1 H), 8.41 (t,J= 1.2 Hz, 1 H), 9.75 (d, J= 8.1 Hz, 1 H).

621
Example 3042
l-Methyl-4-nitro-l//-pyrrole-2-carboxylic acid [cis-4-(quinolin-2-ylamino)-cyclohexyl]-
amide hydrochloride
Step A: Synthesis of l-methyl-4-nitro-l//-pyrrole-2-carboxylic acid [cw-4-(quinolin-2-
ylamino)-cyclohexyl]-amide hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 394, M (free) + H+ ; ]H NMR (300 MHz, CDC13) 6 1.80-2.14 (m, 8 H), 3.91-4.15 (m, 5
H), 6.96 (d, 7-9.4 Hz, 1 H), 7.09 (d, J= 9.0 Hz, 1 H), 7.28-7.31 (m, 1 H), 7.41-7.54 (m, 2 H),
7.67-7.79 (m, 3 H), 8.19 (d, J= 9.6 Hz, 1 H), 9.66 (m, 1 H).
Example 3043
9//-Xanthene-9-carboxylic acid [cw-4-(qiiinolin-2-ylamino)~cyclohexyl]-amide hydrochloride
Step A: Synthesis of 9//-Xanthene-9-carboxylic acid [m-4-(quinolin-2-ylamino)-cyclohexyl]-
amide hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 472, M (free) + Na+ ; !H NMR (300 MHz, CDCI3) 8 1.65-1.89 (m, 8 H), 3.76-3.94 (m,
2 H), 5.99-6.09 (m, 1 H), 6.87 (d,J= 10.1 Hz, 1 H), 7.05-7.18 (m, 4 H), 7.24-7.47 (m, 5 H), 7.65-7.79
(m,3 H) 8.13 (d, .7=9.6 Hz, 1 H), 9.62 (d, J= 7.6 Hz, 1 H).
Example 3044
5-(4-Chloro-phenyl)-furan-2-carboxylicacid [m-4-(quinolin-2-ylamino)-cyclohexyI]-amide
hydrochloride

622
Step A: Synthesis of 5-(4-chloro-phenyl)-furan-2-carboxyIic acid[c/$-4-(quinolin-2-ylamino)-
cyclohexyl]-amide hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 468, M (free) + Na+ ; 'H NMR (300 MHz, CDC13) 5 1.77-2.13 (m, 8 H), 3.93-4.07 (m,
1 H), 4.10-4.28 (m, 1 H), 6.65-7.03 (m, 3 H), 7.12-7.23 (m, I H), 7.32-7.52 (m, 3 H), 7.63-7.85 (m,
5 H), 8.12-8.26 (m, 1 H), 9.74-9.94 (m, 1 H).
Example 3045
3-Nitro-7V-[c«-4-(quinolin-2-ylaniino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 3-nitro-7V-[ciA-4-(quinolin-2-ylamino)-cyclohexyl]-ben2amide
hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 413, M (free) + Na+ ; lHNMR (300 MHz, CDCI3) 5 1.83-2.30 (m, 8 H), 3.99-4.10 (m,
1 H), 4.13-4.31 (m, 1 H), 6.97 (d,J= 9.5 Hz, 1 H), 7.24-7.33 (m, 1 H), 7.42-7.51 (m, 1 H), 7.63 (t,
J= 1.9 Hz, 1 H), 7.70-7.79 (m, 3 H), 8.17-8.24 (m, 2 H), 8.30-8.35 (m, 1 H), 8.75-8.77 (m, 1 H), 9.76
(d,J=7.3Hz, 1H).
Example 3046
4-Fluoro-3-methyl-Ar-[cw-4-(quinolin-2-ylamino)-cyC1-5hexyl]-benzamide hydrochloride
Step A: Synthesis of 4-fluoro-3-methyl-iV-[c/$-4-(quinolin-2-ylamino)-cyclohexyl]-
benzamide hydrochloride.
To a solution of ci5-A/-quinolin-2-yl-cyclohexane-l,4-diamine obtained in step A of example
3033 (250 mg, 1.04 mmol) in CHCI3 (5 mL) were added Et3N (0.3 mL, 2.15 mmol) and
4-fluoro-3-methyI-benzoyl chloride (197 mg, 1.14 mmol). The mixture was stirred at ambient

623
temperature for 12 hr. The reaction was quenched with saturated aqueous NaHCO3 and the aqueous
layer was extracted with CHC13 (three times). The combined organic layer was dried over MgSOj,
filtered, concentrated, purified by medium-pressure liquid chromatography (NH-silica gel, 20% to
50% EtOAc in hexane). To a solution of the above material in EtOAc (2 mL) was added 4 M
hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 2 hr and
concentrated. The residue was suspended in Et2O (20 mL) and the suspension was stirred at ambient
temperature for 6 hr. The precipitate was collected by filtration, washed with Et?O, and dried at 80 °C
under reduced pressure to give 4-fluoro-3-methyl-Ar-[c/j-4-(quinolin-2-ylamino)-cyclohexyl]-
benzamide hydrochloride (363 mg, 85%) as a white solid.
ESI MS m/e 400, M (free) + Na+ ; *H NMR (300 MHz, CDC13) 5 1.82-2.10 (m, 8 H), 2.32 (d, J= 1.9
Hz, 3 H), 3.96-4.07 (m, 1 H), 4.09-4.27 (m, 1 H), 6.62-6.72 (m, 1 H), 6.96 (d, J= 9.5 Hz, 1 H), 7.04
(t,y=8.9Hz, 1 H), 7.40-7.51 (m, 1 H), 7.61-7.83 (m, 5 H) 8.19 (d,J= 9.6 Hz, 1 H), 9.71-9.85 (m,
1H).
Example 3047
3-Bromo-Ar-[cw-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of S-bromo-A^Ic&^-tquinolin^-ylaminoJ-cyclohexylJ-benzamide
hydrochloride.
Using the procedure for the step A of example 3046, the title compound was obtained.
ESI MS m/e 446, M(free) + Na+ ; 'HNMR (300 MHz, CDCI3) 5 1.81-2.13 (m, 8 H), 3.96-4.08 (m,
1 H), 4.09-4.27 (m, 1 H), 6.84 (d, ,/= 7.8 Hz, 1 H), 6.96 (d, J= 9.6 Hz, 1 H), 7.30 (t, J= 7.9 Hz, 1
H), 7.41-7.50 (m, 1 H), 7.57-7.64 (m, 1 H), 7.69-7.80 (m, 4 H), 8.01 (t, J= 1.6 Hz, 1 H), 8.19 (d, J
= 9.3 Hz, 1 H),9.7i (m, 1 H).
Example 3048

624
2-(2-Bromo-phenoxy)-Af-[ci5-4-(quinolin-2-ylamino)-cyclohexyl]-iiicotinamide hydrochloride
Step A: Synthesis of 2-(2-bromo-phenoxy)-Ar-[cis-4-(quinoliii-2-ylamino)-cyclohexyl]-
nicotinamide hydrochloride.
To a solution of 2-bromo-phenol (453 mg, 2.62 mmol) in DMA (4 mL) was added 60% NaH
in oil (210 mg, 5.24 mmol). The mixture was stirred at ambient temperature for 1 hr. To the mixture
was added 2-chloro-A^[c/5-4-(quinoIin-2-ylamino)-cyclohexyl]-nicotinamide obtained in step A of
example 3037 (1.00 g, 2.62 mmol) in DMA (2 mL). The mixture was stirred at 120 °C for 3 hr and the
reaction was quenched with water. The aqueous layer was extracted with CHCI3 (three times). The
combined organic layer was dried over MgSO4, filtered, concentrated, and purified by medium-
pressure liquid chromatography (NH-si!ica gel, 20% EtOAc in hexane and silica gel, 1% to 2%
MeOH in CHCI3) to give a colorless oil. To a solution of the above material in EtOAc (10 mL) was
added 4 M hydrogen chloride in EtOAc (0.2 mL). The mixture was stirred at ambient temperature for
1 hr and concentrated. The residue was suspended in Et2O (20 mL) and the suspension was stirred at
ambient temperature for 2 hr. The precipitate was collected by filtration, washed with Et2O, and dried
at 60 °C under reduced pressure to give 2-(2-bromo-phenoxy)-jV-[c/s-4-(qumolin-2-ylamino)-
cyclohexyl]-nicotinamide hydrochloride (262 mg, 18%) as a white solid.
ESI MS m/e 517, M (free) + H+ ; lHNMR(300 MHz, CDCI3) 5 1.89-2.17 (m, 8 H), 3.81-3.98 (m, 1
H), 4.14-4.30 (m, 1 H), 6.92 (d, J = 9.5 Hz, I H), 7.11-7.20 (m, 2 H), 7.34-7.47 (m, 3 H), 7.63-7.80
(m, 4 H), 7.92-8.00 (m, 1 H), 8.10-8.20 (m, 2 H), 8.54 (dd, J= 7.5, 2.0 Hz, 1 H), 9.71-9.88 (m, 1 H).
Example 3049
S-Cyano-A'-lcw^-tquinolin^-ylamino^cyclohexylJ-benzamide hydrochloride
Step A: Synthesis of 3-cyano-jV-[C1-5-4-(quinolin-2-ylamino)-cyC1-5hexyl]-benzamide
hydrochloride.
Using the procedure for the step A of example 3046, the title compound was obtained.

625
ESI MS m/e 393, M (free) + Na+ ; ]H NMR (300 MHz, CDCI3) 5 1.80-2.17 (m, 8 H), 3.98-4.30 (m,
2 H), 6.97 (d, 7=9.3 Hz, 1 H), 7.07-7.18 (m, 1 H), 7.42-7.50 (m, 1 H) 7.56 (t, J= 7.8 Hz, I H),
7.70-7.80 (m, 4 H), 8.08 (d, J= 7.9 Hz, 1 H), 8.17-8.25 (m, 2 H), 9.69-9,84 (m, 1 H).
Example 3050
iV-[m-4-(QuinoIin-2-ylamino)-cyclohexyl]-3-trifluoromethyl-benzamidehydrochloride
Step A: Synthesis of Ar-[C1-5-4-(quinolin-2-ylamino)-cyC1-5hexyl)-3-trifluoromethyl-benzamide
hydrochloride.
Using the procedure for the step A of example 3046, the title compound was obtained.
ESI MS m/e 436, M (free) + Na+ ; !HNMR (300 MHz, CDCI3) 5 1.77-2.13 (m, 8 H), 3.97-4.09 (m,
1 H), 4.12-4.33 (m, 1 H), 6.92-7.05 (m, 2 H), 7.41-7.50 (m, 1 H), 7.57 (t, J= 7.7 Hz, 1 H), 7.69-7.79
(m, 4 H), 8.02 (d, J= 8.1 Hz, 1 H), 8.13-8.26 (m, 2 H), 9.72-9.85 (m, 1 H).
Example 3051
Ar-[cw-4-(Quinolin-2-ylamino)-cyclohexyI]-2-/M-tolyloxy-acetamide hydrochloride
Step A: Synthesis of 7V-[c/y-4-(quinoHn-2-yIamino)-cyelohexyl]~2-/M-tolyloxy-
acetamide hydrochloride.
To a solution of m-tolyloxy-acetic acid (189 mg, 1.14 mmol) and cw-JV-quinolin-
2-yl-cyclohexane-l,4-diamine obtained instep A of example 3036 (250 mg, 1.04 mmol) in DMF(15
mL) were added Et3N (0.35 mL, 2.50 mmol), HOBt-H2O (238 mg, 1.56 mmol), and EDC-HC1 (219
g, 1.14 mmol). The reaction mixture was stirred at ambient temperature for 13 hr. To the reaction
mixture was added water (30 mL) and the aqueous layer was extracted with CHC13 (three times). The
combined organic layer was dried over MgSO4, filtered, concentrated, and purified by
medium-pressure liquid chromatography (silica gel, 1% to 5%MeOH in CHCI3) to give a colorless oil.

626
To a solution of the above material in EtOAc (10 mL) was added 4 M hydrogen chloride in EtOAc
(0.2 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated. The residue was
suspended in Et20 (20 mL) and the suspension was stirred at ambient temperature for 2 hr. The
precipitate was collected by filtration, washed with Et3O, and dried at 60 °C under reduced pressure to
give 7*/-[c/5-4-(quinolin-2-ylamino)-cyclohexyl]-2-m-tolyIoxy-acetamide hydrochloride (140 mg,
32%) as a white solid.
ESI MS m/e 412, M(free) + Na+ ; lHNMR (300 MHz, CDC13) 6 1.78-2.06 (m, 8 H), 2.33 (s, 3 H),
3.88-4.12 (m, 2 H), 4.44 (s, 2 H), 6.72-6.96 (m, 5 H), 7.18 (t, J= 8.0 Hz, 1 H), 7.39-7.47 (m, 1 H),
7.68-7.81 (m, 3 H), 8.17 (d, .7=9.3 Hz, 1 H), 9.72-9.89 (m, 1 H).
Example 3052
Z^-Diphenyl-A^m^-tquinolin^-ylamino^cyclohexylJ-acetamide hydrochloride
Step A: Synthesis of 2,2-diphenyl-7V-[c/s-4-(quinolin-2-ylamino)-cyC1-5hexyl]-
acetamide hydrochloride.
Using the procedure for the step A of example 3046, the title compound was obtained.
ESI MS m/e 458, M (free) + Na+ ; !HNMR (300 MHz, CDC13) 5 1.71-1.97 (m, 8 H), 3.84-4.10 (m,
2 H), 4.87 (s,lH), 6.16-6.25 (m, 1 H), 6.90 (d, 7= 9.5 Hz, 1 H), 7.20-7.36 (m, 10 H), 7.39-7.48 (m,
1 H), 7.67-7.79 (m, 3 H), 8.15 (d, J= 9.2 Hz, 1 H), 9.63-9.77 (m, 1 H).
Example 3053
5-Bromo-furan-2-carboxylic acid [c/s-4-(qiiinolin-2-ylamino)-cyclohexyl]-amide hydrochloride
Step A: Synthesis of 5-bromo-furan-2-carboxylic acid [m-4-(quinolin-2-ylamino)-cyclohexyl]-
amide hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.

627
ESI MS m/e 436, M (free) + Na+ ; 'H NMR (300 MHz, CDC13) 5 1.84-2.09 (m, 8 H), 3.92-4.18 (m,
2 H), 6.42 (d, 7= 3.5 Hz, 1 H), 6.61 (d, J= 8.6 Hz, 1 H), 6.95 (d, J= 8.2 Hz, 1 H), 7.05 (d, J = 3.5
Hz, 1 H), 7.42-7.48 (m, 1 H), 7.69-7.83 (m, 3 H), 8.19 (d,J= 9.5 Hz, 1 H), 9.85 (d,7= 8.6 Hz, 1 H).
Example 3054
2-(4-FIuoro-phenoxy)-AL[c/5-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide hydrochloride
Step A: 2-(4-fluoro-phenoxy)-nicotinic acid ethyl ester.
To a solution of 2-fluoro-phenol (3.02 g, 26.9 mmol) in DMA (20 mL) was added 60% NaH
in oil (1.08 mg, 26.9 mmol). The mixture was stirred at ambient temperature for 1.5 hr. To the
mixture was added 2-chloro-nicotinic acid ethyl ester (5.00 g, 26.9 mmol) in DMA (5 mL). The
mixture was stirred at 120 °C for 2 hr and the reaction was quenched with saturated aqueous NaHCO3.
The aqueous layer was extracted with CHCI3 (three times). The combined organic layer was dried
over MgSO4, filtered, and concentrated. The residue was suspended in 10% Et2O in hexane (50 mL)
and the suspension was stirred at ambient tempereture for 1 hr. The precipitate was collected by
filtration, washed with hexane, and dried at 70 °C under reduced pressure to give
2-(4-fluoro-phenoxy)-nicotinic acid ethyl ester (3.08 g, 44%) as a white solid.
ESI MS m/e 284, M + Na+ ; *H NMR (300 MHz, CDC13) 5 1.40 (td, J = 7.1, 1.6 Hz, 3 H), 4.41 (qd,
J= 7.1, 1.6 Hz, 2 H), 6.99-7.21 (m, 5 H), 8.23-8.29 (m, 2 H).
Step B: Synthesis of 2-(4-fluoro-phenoxy)-nicotinic acid.
To a solution of 2-(4-fluoro-phenoxy)-nicotinic acid ethyl ester (3.00 g, 11.5 mmol) in EtOH
(90 mL) was added 2 M aqueous NaOH (6 mL). The mixture was stirred at ambient temperature for
4 hr. To the mixture was added 1 M aqueous HC1 (pH=3) and concentrated. The residue was
dissolved in water and the aqueous layer was extracted with CHCI3 (three times). The combined
organic layer was dried over MgSO4, filtered, and concentrated. The residue was suspended in 10%
Et2O in hexane (80 mL) and the suspension was stirred at ambient tempereture for 1 hr. The

628
precipitate was collected by filtration, washed with hexane, and dried at 70 °C under reduced pressure
to give 2-(4-fluoro-phenoxy)-nicotinic acid (2.39 g, 89%) as a white solid.
ESI MS m/e 233, M+ ; !H NMR (300 MHz, CDC13) 5 7.05-7.25 (m, 5 H), 8.32 (dd, J= 4.8, 2.0 Hz,
1 H), 8.49 (dd, J= 7.6, 2.0 Hz, 1 H).
Step C: Synthesis of 2-(4-fluoro-phenoxy)-Ar-[c/s-4-(quinolin-2-ylamino)-cyC1-5hexyl]-
nicotinamide hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 479, M(free) +Na+ ; !HNMR (300 MHz, CDCi3) 6 1.83-2.14 (m, 8 H), 3.88-4.01 (m,
1 H), 4.13-4.30 (m, 1 H), 6.93 (d,J= 9.3 Hz, 1 H), 7.11-7.20 (m, 3 H), 7.25-7.31 (m, 2 H), 7.43 (t,
.7=7.9 Hz, 1 H), 7.67-7.81 (m, 3 H), 7.93 (d, 7= 7.2 Hz, 1 H), 8.16 (d, 7= 9.2 Hz, 1 H), 8.21 (dd, J
= 4.8, 2.0 Hz, 1 H), 8.54 (dd, 7=7.6,2.0 Hz, 1 H), 9.81-9.94 (m, 1 H).
Example 3055
2-(3,4-Difluoro-phenoxy)-Ar-[c/j-4-(quinoIin-2-yIamino)-cyC1-5hexyI]-nicotinamide
hydrochloride
Step A: Synthesis of 2-(3,4-difluoro-phenoxy)-nicotinic acid.
To a solution of 3,4-difluoro-phenol (3.77 g, 28.9 mmol) in DMA (20 mL) was added 60%
NaH in oil (1.16 mg, 28.9 mmol). The mixture was stirred at ambient temperature for 1 hr. To the
mixture was added 2-chloro-nicotinic acid ethyl ester (5.36 g, 28.9 mmol) in DMA (5 mL). The
mixture was stirred at 120 °C for 2.5 hr and the reaction was quenched with saturated aqueous
NaHCO3. The aqueous layer was extracted with CHC13 (three times). The combined organic layer
was dried over MgSO4, filtered, and concentrated. The residue was suspended in 10% Et2O in hexane
(150 mL) and the suspension was stirred at ambient tempereture for 1 hr. The precipitate was filtered,
washed with hexane, and dried at 70 °C under reduced pressure to give a white solid. To a solution
of the above material inEtOH(150mL) was added 2 M aqueous NaOH( 15.2 mL). The mixture was

629
stirred at ambient temperature for 12 hr. To the mixture was added 1 M aqueous HC1 (46 mL, pH=3)
and concentrated. The residue was dissolved in water and the aqueous layer was extracted with CHCI3
(three times). The combined organic layer was dried over MgSC>4, filtered, and concentrated. The
residue was suspended in 10% Et2O in hexane (150 mL) and the suspension was stirred at ambient
tempereture for 30 min. The precipitate was collected by filtration, washed with hexane, and dried at
70 °C under reduced pressure to give 2-(3,4-difluoro-phenoxy)-nicotinic acid (4.85 g, 67) as a white
solid.
ESI MS m/e 251, M+ ; ]H NMR (300 MHz, CDC13) 5 6.90-7.30 (m, 4 H), 8.30-8.35 (m, 1 H),
8.46-8.52 (m, 1 H).
Step B: Synthesis of 2-(3,4-difluoro-phenoxy)-Ar-[c«-4-(quinolin-2-ylamino)-cyclohexyl]-
nicotinamide hydrochloride
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 475, M(free) + H+ ; 'H NMR (300 MHz, CDCI3) 6 1.85-2.13 (m, 8 H), 3.91-4.03 (m, 1
H), 4.13-4.29 (m, 1 H), 6.94 (d, J = 9.6 Hz, 1 H), 7.11-7.34 (m, 4 H), 7.40-7.47 (m, 1 H), 7.67-7.85
(m,4H), 8.17 (d, .7=9.5 Hz, I H), 8.22 (dd, 7 = 4.8, 2.0 Hz, 1 H), 8.53 (dd, J= 1.6, 2.0 Hz, 1 H),
9.84-9.98 (m, 1 H).
Example 3056
7V-[c/5-4-(QuinoIin-2-ylamino)-cyC1-5hexyl]-2-/7-toIyloxy-nicotinainide hydrochloride
Step A: Synthesis of 2-/>-tolyloxy-nicotinic acid.
Using the procedure for the step A of example 3055, the title compound was obtained.
ESI MS m/e 229, M+ ; 'H NMR (300 MHz, CDC13) 5 2.40 (s, 3 H) 7.05-7.31 (m, 5 H), 8.30-8.35 (m,
1 H), 8.52-8.57 (m, 1 H).
Step B: Synthesis of iV-[m-4-(quinolin-2-ylamino)-cyclohexyl]-2-p-tolyloxy-nicotinamide

630
hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 475, M (free) + Na+; !H NMR (300 MHz, CDC13) 5 1.86-2.13 (m, 8 H), 2.36 (s, 3 H),
3.86-3.98 (m, 1 H), 4.11-4.29 (m, 1 H), 6.86-7.00 (m, 1 H), 7.07-7.31 (m, 5 H), 7.43 (t,J= 7.6 Hz,
1 H), 7.64-7.82 (m, 3 H), 7.92-8.28 (m, 3 H), 8.53 (d, J= 7.0 Hz, 1 H), 9.74-9.87 (m, 1 H).
Example 3057
2-(4-Chloro-phenoxy)-Ar-[cw-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide hydrochloride
Step A: Synthesis of 2-(4-chloro-phenoxy)-nicotinic acid.
Using the procedure for the step A of example 3055, the title compound was obtained.
ESI MS m/e 250, M+ H" ; lH NMR (300 MHz, CDC13) 5 7.10-7.21 (m, 3 H), 7.36-7.45 (m, 2 H),
8.30-8.36 (m, 1 H), 8.45-8.51 (m, 1 H).
Step B: Synthesis of 2-(4-chIoro-phenoxy)-7V-[c/s-4-(quinolin-2-ylamino)-
cyclohexylj-nicotinamide hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 473, M + H+ ; 'H NMR (300 MHz, CDCI3) 6 1.83-2.13 (m, 8 H), 3.87-4.04 (m, 1 H),
4.10-4.33 (m, 1 H), 6.87-7.01 (m, 1 H), 7.10-7.35 (m, 3 H), 7.38-7.50 (m, 3 H), 7.65-7.93 (m, 4 H),
8.10-8.26 (m, 2 H), 8.53 (d, J= 6.4 Hz, 1 H), 9.78-9.97 (m, 1 H).
Example 3058
2-(4-Bromo-phenoxy)-Ar-[cw-4-(quinolin-2-ylamino)-cyclohexyl]-
nico tin amide hydrochloride
Step A: 2-(4-bromo-phenoxy)-nicotinic aeid

631
Using the procedure for the step A of example 3055, the title compound was obtained.
ESI MS m/e 294, M + H+ ; 'HNMR (300 MHz, CDC13) 6 7.05-7.12 (m, 2 H), 7.18 (dd,7= 7.6, 4.8
Hz, 1 H), 7.52-7.62 (m, 2 H), 8.31-8.35 (m, 1 H), 8.48 (dd,J = 7.6, 2.0 Hz, 1 H).
Step B: Synthesis of 2-(4-bromo-phenoxy)-JV-[c/y-4-{qiiinoHn-2-ylamino)-
cyclohexylj-nicotinamide hydrochloride
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 517, M(free) + H+ ; 'H NMR (300 MHz, CDC13) 5 1.80-2.11 (m, 8 H), 3.87-4.02 (m, 1
H), 4.12-4.30 (m, 1 H), 6.86-7.01 (m, 1 H), 7.09-7.29 (m, 3 H), 7.38-7.48 (m, 1 H), 7.51-7.62 (m, 2
H), 7.64-7.93 (m, 4 H), 8.11-8.25 (m, 2 H), 8.53 (d,J= 7.6 Hz, 1 H), 9.78-9.96 (m, 1 H).
Example 3059
2-(4-Methoxy-phenoxy)-iV-[c/£-4-(qiiinolin-2-yIamMo)-cyclohexyl]-
nicotinamide hydrochloride
Step A: Synthesis of 2-(4-methoxy-phenoxy)-nicotinic acid.
Using the procedure for the step A of example 3055, the title compound was obtained.
ESI MS m/e 245, M+ ; lH NMR (300 MHz, CDC13) 5 6.94-7.01 (m, 2 H), 7.09-7.20 (m, 3 H),
8.31-8.35 (m, 1 H), 8.50-8.55 (m, 1 H).
Step B: Synthesis of 2-(4-methoxy-phenoxy)-iV-[cis-4-(quinolin-2-ylamino)-
cyclohexyl]-nicotinamide hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 491, M (free) + Na+ ; *H NMR (300 MHz, CDC13) 6 1.85-2.12 (m, 8 H), 3.81 {brs, 3 H),
3.86-3.99 (m, 1 H), 4.12-4.30 (m, 1 H), 6.84-7.29 (m, 6 H), 7.37-7.49 (m, 1 H), 7.64-7.82 (m, 3 H),
7.96-8.28 (m, 3 H), 8.48-8.60 (m, 1 H), 9.71-9.86 (m, 1 H).

632
Example 3060
2-(3-Chloro-4-fluoro-phenoxy)-7V-(C1-5-4-(quinolin-2-ylamino)-cyclohexyI]-
nicotinamide hydrochloride
Step A: Synthesis of 2-(3-chloro-4-fluoro-phenoxy)-nicotinic acid.
Using the procedure for the step A of example 3055, the title compound was obtained.
ESI MS m/e 268, M + H+ ; *H NMR (200 MHz, CDC13) 5 7.03-7.32 (m, 4 H), 8.29-8.37 (m, 1 H),
8.44-8.53 (m, 1 H).
Step B: Synthesis of 2-(3-chloro-4-fluoro-phenoxy)-Ar-[m-4-(quinolin-2-ylamino)-
cyclohexylj-nicotinamide hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 491, M(free) + H* ; lHNMR (300 MHz, CDC13) 5 1.83-2.10 (m, 8 H), 3.88-4.04 (m, 1
H), 4.11-4.27 (m, 1 H), 6.92 (d, J= 9.6 Hz, 1 H) 7.16 (dd, J= 1.6, 4.8 Hz, 1 H), 7.21-7.46 (m, 4 H),
7.67-7.81 (m,4H), 8.15 (d, J= 9.5 Hz, I H), 8.20 (dd5 J= 4.8, 2.0 Hz, 1 H), 8.52 (dd,J= 7.6, 2.0
Hz, 1 H), 9.83-9.95 (m, 1 H).
Example 3061
Ar-[as-4-(Quinolin-2-ylamiiio)-cyclohexyl]-2-/M-tolyloxy-nicotinaniide hydrochloride
Step A: Synthesis of 2-m-tolyloxy-nicotinic acid
Using the procedure for the step A of example 3055, the title compound was obtained.
ESI MS m/e 229, M+ ; lU NMR (200 MHz, CDC!3) 5 2.40 (s, 3 H), 6.95-7.41 (m, 5 H), 8.33 (dd, J
= 4.8, 1.8 Hz, 1 H), 8.54 (dd, 7=7.7, 1.9 Hz, 1 H).
Step B: Synthesis of Ar-[c/5-4-(quinolin-2-ylamino)-cyclohexyll-2-/M-tolyloxy-nicotinamide

633
hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 475, M + Na+ ; ]H NMR (300 MHz, CDC13) 5 1.87-2.07 (m, 8 H), 2.40 (s, 3 H), 3.85-3.98
(m, 1 H), 4.10-4.25 (m, I H), 6.88-6.99 (m, I H), 7.01-7.18 (m, 4 H), 7.33 (t, J= 7.8 Hz, 1 H), 7.42
(t, J= 7.5 Hz, I H), 7.66-7.81 (m, 3 H), 7.93-8.03 (m, 1 H), 8.12-8.20 (m, 1 H), 8.23 (dd, J= 4.7, 1.9
Hz, 1 H), 8.52 (dd,7= 7.5, 1.9 Hz, 1 H), 9.71-9.83 (m, 1 H).
Example 3062
2-(3-Methoxy-phenoxy)-AL[c/s-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide hydrochloride
Step A: Synthesis of (3-methoxy-phenoxy)-acetic acid ethyl ester.
To a solution of 3-methoxy-phenol (3.54 g, 28.5 mmol) in DMA (20 mL) was added 60%
NaH in oil (1.14 g, 28.5 mmol). The mixture was stirred at ambient temperature for 1.5 hr. To the
mixture was added bromo-acetic acid ethyl esterr (4.53 g, 28.5 mmol) in DMA (10 mL). The mixture
was stirred at ambient temperature for 1.5 hr and the reaction was quenched with saturated aqueous
NaHCC>3- The aqueous layer was extracted with CHCI3 (three times). The combined organic layer
was dried over MgSO4, filtered, concentrated, and purified by medium-pressure liquid
chromatography (silica gel, 20% EtOAc in hexane) to give (3-methoxy-phenoxy)-acetic acid ethyl
ester (5.19 g, 91%) as a colorless oil.
ESI MS m/e 233, M + Na+ ; !HNMR (300 MHz, CDC13) 5 1.30 (t, J= 7.1 Hz, 3 H), 3.79 (s, 3 H), 4.27
(q, J= 7.1 Hz, 2 H), 4.60 (s, 2 H), 6.44-6.61 (m, 3 H), 7.15-7.23 (m, 1 H).
Step B: Synthesis of (3-methoxy-phenoxy)-acetic acid.
To a solution of (3-methoxy-phenoxy)-acetic acid ethyl ester (5.06 g, 24.1 mmol) in EtOH
(100 mL) was added 1 M aqueous NaOH (25.3 mL). The mixture was stirred at ambient temperature
for 1 hr. To the mixture was added 1 M aqueous HC! (pH=3) and concentrated. The residue was
dissolved in water and the aqueous layer was extracted with CHC13 (three times). The combined

634
organic layer was dried over MgSC>4, filtered, and concentrated to give (3-methoxy-phenoxy)-acetic
acid (4.05 g, 92%) as a white solid.
ESI MS m/e 182, M+ ; 'H NMR (300 MHz, DMSO-d6) 5 3.73 (s, 3 H), 4.65 (s, 2 H), 6.45-6.57 (m,
3 H), 7.13-7.23 (m, 1 H), 12.97 (brs, 1 H).
Step C: Synthesis of 2-(3-methoxy-phenoxy)-A'-[c/y-4-(quinoHii-2-ylamino)-cyclohexyl]-
acetamide hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 406, M (free) + H+ ; lH NMR (300 MHz, CDC13) 5 1.79-2.05 (m, 8 H), 3.82 (s, 3 H),
3.90-4.11 (m, 2 H), 4.46 (s, 2 H), 6.52-6.61 (m, 3 H), 6.80-6.87 (m, 1 H), 6.93 (d, J= 9.5 Hz, 1 H),
7.16-7.24 (m, 1 H), 7.41-7.48 (m, 1 H), 7.69-7.82 (m, 3 H), 8.17 (d, J= 9.5 Hz, 1 H) 9.78-9.88 (m,
1H).
Example 3063
2-(3-Chloro-phenoxy)-Ar-[cw-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide hydrochloride
Step A: Synthesis of (3-chloro-phenoxy)-acetic acid ethyl ester.
Using the procedure for the step A of example 3062, the title compound was obtained.
ESI MS m/e 237, M +Na+ ; ]H NMR (300 MHz, CDC13) 5 1.30 (t, J= 7.2 Hz, 3 H), 4.28 (q, J= 7.2
Hz, 2 H), 4.60 (s, 2 H), 6.73-7.02 (m, 3 H), 7.14-7.30 (m, 1 H).
Step B: Synthesis of (3-chloro-phenoxy)-acetic acid.
Using the procedure for the step B of example 3062, the title compound was obtained.
ESI MS m/e 187, M + H+ ; ]HNMR (300 MHz, CDC13) 5 4.73 (d, J= 1.2 Hz, 2 H), 6.87-6.94 (m, 1
H), 6.98-7.05 (m, 2 H), 7.27-7.35 (m, 1 H), 13.07 (s, 1 H).
Step C: Synthesis of 2-(3-chloro-phenoxy)-iV-[C1-5-4-(quinoIin-2-ylaniino)-cyclohexyI]-

635
acetamide hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 410, M (free) + H+ ; 'H NMR (300 MHz, CDC13) 5 1.78-2.07 (m, 8 H), 3.90-4.14 (m, 2
H), 4.45 (s, 2 H) 6.74-6.84 (m, 1 H), 6.86-7.03 (m, 4 H), 7.20-7.29 (m, 1 H), 7.40-7.49 (m, 1 H),
7.69-7.82 (m, 3 H), 8.18 (d, J = 9.3 Hz, I H), 9.79-9.93 (m, 1 H).
Example 3064
2-(3-Chloro-4-fluoro-phenoxy)-7V-[c/y-4-(quinolin-2-ylamino)-cyC1-5hexyl]-acetamide
hydrochloride
Step A: Synthesis of (3-chloro-4-fluoro-phenoxy)-acetic acid ethyl ester.
Using the procedure for the step A of example 3062, the title compound was obtained.
ESI MS m/e 233, M + H+ ; lU NMR (300 MHz, CDC13) 8 1.30 (t, J= 7.1 Hz, 3 H), 4.28 (q, J= 7.1
Hz, 2 H), 4.58 (s, 2 H), 6.75-6.82 (m, 1 H), 6.95 (dd, 7= 5.9, 3.1 Hz, 1 H), 7.01-7.11 (m, 1 H).
Step B: Synthesis of (3-chloro-4-fluoro-phenoxy)-acetic acid.
Using the procedure for the step B of example 3062, the title compound was obtained.
ESI MS m/e 205, M + H+ ; 'H NMR (300 MHz, DMSO-d6) 8 4.72 (s, 2 H), 6.92-6.97 (m, 1 H), 7.17
(dd, .7=6.1, 3.1 Hz, 1 H), 7.34 (t, J = 9.1 Hz, 1 H), 13.08 (brs, 1 H).
Step C: Synthesis of 2-(3-ehIoro-4-fluoro-phenoxy)-Ar-[c/y-4-(quinolin-2-ylamino)-
cyclohexyl]-acetamide hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 450, M (free)+ Na+; 'HNMR (300 MHz, CDC13) 8 1.76-2.08 (m, 8 H), 3.91-4.13 (m,
2 H), 4.42 (s, 2 H), 6.73-6.97 (m, 3 H), 7.00-7.14 (m, 2 H), 7.41-7.49 (m, 1 H), 7.70-7.80 (m, 3 H),
8.18 (d, J = 9.5 Hz, 1 H), 9.79-9.90 (m, 1 H).

636
Example 3065
2-(3,4-Dichloro-phenoxy)-AL[a5-4-(quinoUn-2-ylamino)-cyclohexyl]-acetamide hydrochloride
Step A: Synthesis of (3,4-dichloro-phenoxy)-acetic acid ethyl ester.
Using the procedure for the step A of example 3062, the title compound was obtained.
CI MS m/e 249, M+ ; *H NMR (300 MHz, CDC13) 5 1.30 (t, 7= 7.1 Hz, 3 H), 4.28 (q, 7 = 7.1 Hz, 2
H), 4.59 (s, 2 H), 6.78 (dd, 7= 9.0, 2.9 Hz, 1 H), 7.01 (d, .7=2.8 Hz, 1 H), 7.34 (d, 7=9.1 Hz, 1 H).
Step B: Synthesis of (3,4-dichloro-phenoxy)-acetic acid.
Using the procedure for the step B of example 3062, the title compound was obtained.
ESI MS m/e 221, M + H+ ; *H NMR (300 MHz, DMSO-d6) 5 4.76 (s, 2 H), 6.96 (dd, 7 = 8.9, 2.9 Hz,
1 H), 7.24 (d, 7= 2.9 Hz, 1 H), 7.53 (d,7= 8.9 Hz, 1 H), 13.12 (brs, 1 H).
Step C: Synthesis of 2-(3,4-dichloro-phenoxy)-AT-[cK-4-(quinolin-2-ylamino)-cyclohexyl]-
acetamide hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 466, M (free) + Na+ ; 'H NMR (300 MHz, CDC13) 6 1.75-2.07 (m, 8 H), 3.92-4.13 (m,
2 H), 4.44 (s, 2 H), 6.78 (d,7= 8.1 Hz, 1 H), 6.86-6.97 (m, 2 H), 7.10 (d,7= 2.9 Hz, 1 H), 7.37 (d,
7= 8.9 Hz, 1 H), 7.41-7.49 (m, 1 H), 7.67-7.82 (m, 3 H), 8.18 (d, 7= 9.5 Hz, 1 H), 9.80-9.90 (m, H).
Example 3066
C-(Methyl-phenyl-amino)-7V-[c/y-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide
dihydrochloride
Step A: Synthesis of (methyl-phenyl-amino)-acetic acid ethyl ester.

637
To a solution of bromo-acetic acid ethyl ester (5.00 g, 29.9 mmol) in IPA (10 mL) were added
z-Pr2NEt (4.06 g, 31.4 mmol) and methyl-phenyl-amine (3.37 g, 31.4 mmol). The mixture was stirred
at reflux for 2.5 hr and the reaction was quenched with saturated aqueous NaHCO3. The aqueous
layer was extracted with CHC13 (three times). The combined organic layer was dried over MgSO4,
filtered, concentrated, and purified by medium-pressure liquid chromatography (silica gel, 20%
EtOAc in hexane) to give (methyl-phenyl-amino)-acetic acid ethyl ester (5.61 g, 97%) as a yellow oil.
ESIMSm/e216,M + Na+;'HNMR(300MHz,CDCl3)ol.24(t,J=7.1Hz,3H),3.07(s,3H),4.05
(s, 2 H), 4.17 (q, J= 7.1 Hz, 2 H), 6.63-6.79 (m, 3 H), 7.18-7.29 (m, 2 H).
Step B: Synthesis of (methyl-phenyl-amino)-acetic acid.
To a solution of (methyl-phenyl-amino)-acetic acid ethyl ester (5.48 g, 28.4 mmol) in EtOH
(100 mL) was added 1 M aqueous NaOH (29.8 mL). The mixture was stirred at ambient temperature
for 1.5 hr. To the mixture was added 1 M aqueous HC1 (pH=3) and concentrated. The residue was
dissolved in water and the aqueous layer was extracted with CHC13 (three times). The combined
organic layer was dried over MgSO4, filtered, concentrated, and purified by medium-pressure liquid
chromatography (silica gel, 20% EtOAc in hexane) to give (methyl-phenyl-amino)-acetic acid (1.73
g, 37%) as a yellow oil.
ESI MS m/e 165, M+ ; 'H NMR (300 MHz, CDCI3) 8 3.05 (s, 3 H), 4.07 (s, 2 H), 6.65-6.85 (m, 3 H),
7.18-7.30 (m, 2 H), 8.62 (brs, 1 H).
Step C: Synthesis of C-(methyl-phenyl-amino)-iV-[cw-4-(quinolin-2-ylamino)-
cyclohexylj-acetamide dihydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 411, M(free) + Na+;1H NMR (300 MHz, CDCI3) 5 1.73-1.99 (m, 8 H), 3.05-3.16 (m,
3 H), 3.79-4.02 (m, 4 H), 6.82-7.00 (m, 4 H), 7.06-7.49 (m, 5 H), 7.65-7.80 (m, 3 H), 8.15 (d, J= 9.9
Hz, 1 H), 9.57-9.68 (m, 1 H).

638
Example 3067
2-(3,4-Dichloro-phenylamino)-AL[m-4-(quinolin-2-ylamino)-cyclohexyl]-acetainide
dihydrochloride
Step A: Synthesis of (3,4-dichloro-phenylamino)-acetic acid ethyl ester.
Using the procedure for the step A of example 3066, the title compound was obtained.
CI MS m/e 248, M + H+ ; ]H NMR (300 MHz, CDC13) 5 1.31 (t, J= 7.1 Hz, 3 H), 3.85 (d, J= 5.4 Hz,
2H),4.26(q,J=7.1 Hz, 2 H), 4.33-4.42 (m, 1 H), 6.45 (dd, J= 8.7, 2.8 Hz, 1 H), 6.66 (d,J = 2.8
Hz, 1 H), 7.21 (d,J= 8.7 Hz, 1 H).
Step B: Synthesis of (3,4-dichloro-phenylamino)-acetic acid.
Using the procedure for the step B of example 3054, the title compound was obtained.
ESI MS m/e 220, M + H+ ; !H NMR (300 MHz, CDC13) 5 3.84 (s, 2 H), 6.37 (brs, 1 H), 6.57 (dd, J
= 8.8, 2.7 Hz, 1 H), 6.76 (d, .7=2.6 Hz, 1 H), 7.26 (d, 7= 8.8 Hz, 1 H), 12.67 (brs, 1 H).
Step C: Synthesis of 2-(3,4-dichloro-phenylamino)-7V-[c/5-4-(quinolin-2-ylamino)-
cyclohexylj-acetamide dihydrochloride
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 465, M (free) + Na+ ; *H NMR (300 MHz, CDCl3) 5 1.72-2.05 (m, 8 H), 3.80 (s, 2 H),
3.87-4.10 (m, 2 H), 6.48-6.57 (m, 1 H), 6.73 (brs, 1 H), 6.86-7.05 (m, 2 H), 7.18 (d,J = 8.7 Hz, 1 H),
7.39-7.50 (m, 1 H), 7.66-7.80 (m, 3 H), 8.11-8.24 (m, 1 H), 9.55-9.68 (m, 1 H).
Example 3068
3,4-Difluoro-Ar-[cis-4-(quinolin-2-ylamino)-cyclohexylmethyI]-benzamide hydrochloride
Step A: Synthesis of (m-4-hydroxymethyl-cyclohexyl)-carbamic acid /erf-butyl ester.
A suspension of cw-4-amino-cyC1-5hexanecarboxylic acid (244 g, 1.70 mol) in MeOH (2.45

639
L) was cooled to -8 °C . Thionyl chloride (45.0 mL, 617 mmol) was added dropwise. The resulting
solution was stirred at ambient temperature for 4.5 hr and concentrated to give a white solid. To a
suspension of the above solid in CHC13(3.OO L) were added triethylamine (261 mL, 1.87 mol) and
(Boc)20 (409 g, 1.87 mol) successively. The reaction mixture was stirred at ambient temperature for
5 hr and poured into water. The aqueous layer was extracted with CHCI3 (three times). The combined
organic layer was dried over MgSO4, filtrated, concentrated, and purified by flash chromatography
(silica gel, CHC13 only to 10% MeOH in CHCI3) to give a colorless oil (531 g). To a suspension
cooled at -4 °C of lithium aluminum hydride (78.3 g, 2.06 mol) in Et2O (7.9 L) was added a solution
of the above oil (530.9 g) in Et2O (5.3 L) below 0 °C. The resulting suspension was stirred at ambient
temperature for 2 hr. The reaction mixture was cooled on an ice-bath, quenched with cold water, and
filtrated through a pad of celite. The filtrate was dried over MgSO4, filtrated, and concentrated. The
precipitate was suspended in hexane (300 mL), filtrated, washed with hexane, and dried under
reduced pressure to give (czs-4-hydroxymethyl-cyclohexyl)-carbamic acid /er/-butyl ester (301 g,
77%) as a white solid.
ESIMSm/e252,M + Na+;iHNMR(300MHz,CDCl3)51.16-1.36(rn,2H), 1.45 (s, 9 H), 1.52-1.77
(m, 7 H), 3.51 (d, J= 6.2 Hz, 2 H), 3.75 (brs, 1 H), 4.30-4.82 (m, 1 H).
Slep B: Synthesis of [c/s-4~(benzyloxycarbonylamino~methyl)-cyclohexyl]-carbamic acid
tert-buty\ ester.
To a solution of (c/s-4-hydroxymethyl-cyclohexyI)-carbamic acid tert-butyl ester (17.7 g,
77.2 mmol) in THF (245 mL) were added triphenylphosphine (20.2 g, 77.0 mmol) and phthalimide
(11.4 g, 77.5 mmol) successively. The resulting suspension was cooled on an ice-bath and 40%
diethyl azodicarboxylate (DEAD) in toluene (33.6 mL, 74.1 mmol) was added over 1 hr. The reaction
mixture was stirred at ambient temperature for 2.5 days, concentrated, and purified by flash
chromatography (silica gel, 33% EtOAc in hexane) to give a white solid. To a suspension of the above
solid (27.5 g) in EtOH (275 mL) was added hydrazine hydrate (5.76 g, 115 mmol). The mixture was
stirred at reflux for 2.25 hr, cooled, and concentrated. The precipitate was dissolved in 10% aqueous
sodium hydroxide (350 mL). The aqueous layer was extracted with CHC13 (three times). The

640
combined organic layer was dried over MgSO4, filtrated, and concentrated. To a solution of the above
residue in CHC13 (275 mL) was added triethylamine (8.54 g, 84.4 mmol). The resulting solution was
cooled to 0 °C and ZCI (14.4 g, 84.4 mmol) was added below 5 °C. The reaction mixture was stirred
at ambient temperature for 16 hr and poured into saturated aqueous NaHCO3. The aqueous layer was
extracted with CHC13 (three times). The combined organic layer was dried over MgSC>4, filtrated,
concentrated, and purified by flash chromatography (silica gel, 2% MeOH in CHC13) to give
[c/s-4-(benzyIoxycarbonylamino-methyl)-cyclohexyI]-carbamic acid tert-butyl ester (25.3 g, 91%) as
a colorless oil.
ESIMSm/e385!M + Na+;IHNMR(300MHz,CDCI3)5 1.13-1.31 (m,2H), 1.44(s,9H), 1.48-1.75
(m, 7 H), 3.10 (t, J= 6.4 Hz, 2 H), 3.72 (brs, 1 H), 4.42-4.76 (m, 1 H), 4.76-4.92 (m, 1 H), 5.09 (s, 2
H), 7.27-7.38 (m, 5 H).
Step C: Synthesis of (c/s-4-amino-cyclohexylmethyl)-carbaniic acid benzyl ester.
To a solution of [c/s-4-(benzyIoxycarbonyIarnino-methyl)-cyclohexyl]-carbamic acid
tert-buty\ ester (12.9 g, 35.6 mmol) in EtOAc (129 mL) was added 4 M hydrogen chloride in EtOAc
(129 mL). The reaction mixture was stirred at ambient temperature for 3 hr, filtrated, washed with
EtOAc, and dried under reduced pressure. The solid was dissolved in saturated aqueous NaHCO3.
The aqueous layer was extracted with CHCI3 (five times). The combined organic layer was dried over
MgSOt, filtrated, concentrated, and dried under reduced pressure to give (c/5-4-amino-
cyctohexylmethyl)-carbamic acid benzyl ester (8.88 g, 95%) as a colorless oil.
ESI MS m/e 263, M + tT;'H NMR (300 MHz, CDCI3) 6 1.36-1.98 (m, 9 H), 2.96-3.32 (m, 3 H), 5.12
(brs, 3 H), 7.36 (s, 5 H).
Step D: Synthesis of (m-4~aminomethyl-cyclohexyl)-quinolin-2-yl-aimne.
A mixture of 2-chloro-quinoItne (10.0 g, 61.1 mmol) and (czs-4-amino-
cyclohexylmethyl)-carbamic acid benzyl ester (17.6 g, 67.2 mmol) in butanol (10 mL) was stirred at
reflux for 2 days. The reaction mixture was poured into saturated aqueous NaHCO3, and the aqueous
layer was extracted with CHC13 (three times). The combined organic layer was dried over MgSO4,

641
filtrated, concentrated, and purified by flash chromatography (NH-silica, 33% to 50% EtOAc in
hexane) to give a pale yellow oil. To a solution of the above oil in MeOH (100 mL) was added 10%
Pd/C (1.00 g). The mixture was stirred at ambient temperature under hydrogen atmosphere for 1.5
days. The reaction mixture was filtrated through a pad of celite, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica gel, 2% MeOH in CHCI3) to give
(c/s-4-aminomethyl-cyclohexyI)-quinoIin-2-yl-amine (6.20 g, 40%) as a pale yellow solid.
ESI MS m/e256,M + HVHNMR (300 MHz, CDC13) 8 1.12-1.51 (m, 4 H), 1.59-1.93 (m, 5 H), 2.60
(d, J= 6.2 Hz, 2 H), 4.08-4.20 (m, 1 H), 4.94 (d, J= 7.4 Hz, 1 H), 6.65 (d, J= 9.0 Hz, 1 H), 7.18 (ddd,
J-7.9, 6.8, 1.1 Hz, 1 H) 7.47-7.59 (m, 2 H), 7.61-7.67 (m, 1 H)7.81 (d,J=8.9Hz, 1 H).
Step E: Synthesis of 3,4-difluoro-Ar-[c/j-4-(quinolin-2-ylamino)-cyclohexylinethyI]-benzainide
hydrochloride.
To asolution of ci's-(4-aminomethyl-cyclohexyl)-quinolin-2-yl-amine (300 mg, 1.17 mmol)
and 3,4-difluoro-benzoic acid (223 mg, 1.41 mmol) in DMF (3 mL) were added Et3N (0.40 mL, 2.87
mmol), HOBt-H2O (270 mg, 1.76 mmol), and EDC-HCI (270 mg, 1.41 mmol). The reaction mixture
was stirred at ambient temperature for 16 hr. To the reaction mixture was added water (20 mL) and the
aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over
MgSO4, filtered, concentrated, and purified by medium-pressure liquid chromatography (NH-silica
gel, 20% to 50% EtOAc in hexane). To a solution of the above material in EtOAc (2 mL) was added
4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 2 hr,
filtered, washed with Et2O, and dried at 80 °C under reduced pressure to give 3,4-difluoro-
A^-[c/5-4-(quinolin-2-ylamino)-cyclohexylmethyl]-benzamide hydrochloride (390 mg, 77%) as a
white solid.
ESI MS m/e 418, M (free) + Na+ ; 'HNMR (300 MHz, CDC13) 5 1.65-2.08 (m, 9 H), 3.48-3.56 (m,
2 H), 3.98-4.09 (m, 1 H), 6.92-7.07 (m, 2 H), 7.18-7.29 (m, 1 H), 7.39-7.47 (m, 1 H), 7.67-7.76 (m,
3 H), 7.81-7.93 (m, 2 H), 8.15 (d,J= 9.6 Hz, 1 H), 9.86-9.95 (m, 1 H).

642
Example 3069
2-Phenoxy-Ar-[cw-4-(quinolin-2~ylamino)-cyC1-5hexylmethyl]-nicotinamide hydrochloride
Step A: Synthesis of 2-phenoxy-Ar-[c«-4-(quinolin-2-ylamino)-cyclohexylmethyl]-nicotinamide
hydrochloride.
Using the procedure for the step E of example 3068, the title compound was obtained.
ESI MS m/e 475, M (free) + Na+ ; *H NMR (300 MHz, CDC13) 5 1.54-2.02 (m, 9 H), 3.42-3.52 (m,
2 H), 3.91-4.05 (m, 1 H), 6.91 (d, J = 9.5 Hz, 1 H), 7.10-7.20 (m, 3 H), 7.23-7.31 (m, 1 H), 7.38-7.50
(m, 3 H), 7.65-7.82 (m, 3 H), 8.06-8.17 (m, 2 H), 8.20 (dd, J = 4.7, 2.0 Hz, 1 H) 8.60 (dd, J= 1.1, 1.9
Hz, 1 H), 9.65-9.78 (m, 1 H).
Example 3070
Ar-[ci5-4-(4-Methyl-quinolin-2-ylamino)-cyclohexyI]-2-phenoxy-nicotinamide hydrochloride
Step A: Synthesis of 7V-(cw-4-methyl-quinolin-2-yl)-cyclohexane-l,4-diamine.
A mixture of 2-Chloro-4-methyl-quinoIine (10.0 g, 56.3 mmol) and
(cw-4-amino-cyclohexyl)-carbamic acid tert-b\ity\ ester obtained in step B of example 3031 (13.3 g,
62.1 mmol) in IPA (10 mL) was stirred at reflux for 7 days. The reaction mixture was poured into
saturated aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (three times). The
combined organic layer was dried over MgSC>4, filtered, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica gel, 20% to 50% EtOAc in hexane) to give a pale
yellow oil. To a solution of the above material in EtOAc (150 mL) was added 4 M hydrogen chloride
in EtOAc (150 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated. The
residue was dissolved in 1 M aqueous NaOH and the aqueous layer was extracted with CHC13 (three
time). The combined organic layer was dried over MgSO4, filtered, and purified by medium-pressure
liquid chromatography (NH-silica gel, 1% to 5% MeOH in CHC13) to give 7V-(cw-4-methyl-
quinolin-2-yl)-cyclohexane-l,4-diamine (3.41 g, 24%) as pale yellow solid.

643
ESIMS m/e256, M + H+;!HNMR(300 MHz, CDC13) 5 l.I9-I.55(m, 4 H), 1.67-1.94 (m, 4 H), 2.56
(s, 3 H), 2.85-2.98 (m, 1 H), 4.03-4.15 (m, 1 H), 4.77 (d,7= 6.8 Hz, 1 H), 6.49 (s, 1 H), 7.17-7.25 (m,
1 H), 7.47-7.55 (m, 1 H), 1.62-1 M (m, 1 H), 7.72-7.77 (m, 1 H).
Step B: Synthesis of A^[ctf-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-2-phenoxy-
nicotinamide hydrochloride.
To a solution of vV-(cz.y-4-methyl-quinolin-2-yl)-cyclohexane-l,4-diamine (300 mg, 1.17
mmol) in CHCI3 (2 mL) were added Et3N (0.45 mL, 2.60 mmol) and 2-phenoxy-nicotinoyl chloride
(411 mg, 1.76 mmol) in CHCI3 (1 mL). The mixture was stirred at ambient temperature for 14 hr. The
reaction was quenched with saturated aqueous NaHCO3 and the aqueous layer was extracted with
CHCI3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated, and
purified by medium-pressure liquid chromatography (NH-silica gel, 20% EtOAc in hexane) to give a
colorless oil. To a solution of the above material in EtOAc (10 mL) was added 4 M hydrogen chloride
in EtOAc (0.2 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated. The
residue was suspended in Et?O (20 mL) and the suspension was stirred at ambient temperature for 2
hr. The precipitate was collected by filtration, washed with EtiO, and dried at 60 °C under reduced
pressure to give 7V-[c/5-4-(4'methyl-quinolin-2-ylamino)-cyclohexyl]-2-phenoxy-nicotinamide
hydrochloride (85 mg, 15%) as a white solid.
ESI MS m/e 453, M (free) + H+ ; 'H NMR (300 MHz, CDC13) 6 1.85-2.12 (m, 8 H), 2.70 (s, 3 H),
3.83-4.00 (m, 1 H), 4.11-4.28 (m, 1 H), 6.74 (s, 1 H), 7.08-7.18 (m, 1 H), 7.19-7.34 (m, 3 H),
7.38-7.53 (m, 3 H), 7.63-7.85 (m, 3 H), 7.91-7.99 (m, 1 H), 8.20-8.24 (m, 1 H), 8.54 (d, 7= 7.4 Hz,
1H).
Example 3071
3,4-Dinuoro-Ar-[cw-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-benzamide hydrochloride

644
Step A: Synthesis of 3,4-difluoro-iV-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
benzamide hydrochloride.
To a solution of 3,4-difluoro-benzoic acid (222 mg, 1.40 mmol) and JV-(cw-4-methyI-
quinolin-2-yl)-cyclohexane-l,4-diamine obtained in step A of example 3070 (300 mg, 1.17 mmol) in
DMF (3 mL) were added Et3N (0.39 mL, 2.80 mmol), HOBt-H2O (268 mg, 1.76 mmol), and
EDC-HC1 (268 g, 1.40 mmol). The reaction mixture was stirred at ambient temperature for 12 hr. To
the reaction mixture was added water (20 mL) and the suspension was stirred at ambient temperature
for 30 min. The precipitated was collected by filtration, washed with H2O, and purified by
medium-pressure liquid chromatography (NH-silica gel, 20% to 50% EtOAc in hexane and silica gel,
2% to 5% MeOH in CHC13) to give a yellow oil. To a solution of the above material in EtOAc (8 mL)
was added 4 M hydrogen chloride in EtOAc (0.5 mL). The mixture was stirred at ambient temperature
for 1 hr and concentrated. The residue was suspended in Et2O (20 mL) and the suspension was stirred
at ambient temperature for 2 hr. The precipitate was collected by filtration, washed with Et2O, and
dried at 60 °C under reduced pressure to give 3,4-difluoro-iV-[c/5-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-benzamide hydrochloride (377 mg, 75%) as a white solid.
ESI MS m/e 396, M (free) + H+ ; 'H NMR (300 MHz, CDC13) 5 1.75-2.17 (m, 8 H), 2.73 (s, 3 H),
3.95-4.26 (m, 2 H), 6.71 (d, .7=7.1 Hz, 1 H), 6.79 (s, 1 H), 7.14-7.28 (m, 1 H), 7.41-7.51 (m, 1 H),
7.54-7.64 (m, 1 H), 7.66-7.79 (m, 3 H), 7.85 (d, J= 8.2 Hz, 1 H), 9.57-9.67 (m, 1 H).
Example 3072
l-(2,3-Dichloro-phenyl)-3-[c/5-4-(4-niethyl-quinolin-2-ylamino)-cyclohexyl]-urea
hydrochloride
Step A: Synthesis of l-(2r3-dichIoro-phenyl)-3-[c/y-4-(4-methyl-quinoIin-2-ylamino)-
cyclohexyl]-urea hydrochloride.
To a solution of AHCIs-4-methyI-quinolin-2-yl)-cyC1-5hexane-l,4-diamine obtained in step A
of example 3070 (300 mg, 1.17 mmol) in DMSO (3 mL) was added l,2-dichloro-3-isocyanato-

645
benzene (242 mg, 1.29 mmol). The mixture was stirred at ambient temperature for 5 hr and poured
into water (20 mL). The precipitate was collected by filtration, washed with water, and purified by
medium-pressure liquid chromatography (NH-siiica gel, 20% to 33% EtOAc in hexane) and flash
chromatography (silica gel, 2% MeOH in CHC13) to give a pale yellow oil. To a solution of the above
material in EtOAc (10 mL) was added 4 M hydrogen chloride in EtOAc (0.2 mL). The mixture was
stirred at ambient temperature for 1 hr and concentrated. A suspension of the residue in Et2O (20 mL)
was stirred at ambient tempareture for 1 hr. The precipitate was collected by filtration, washed with
Et2O, and dried at 60 °C under reduced pressure to give l-(2,3-dichloro-phenyl)-3-[c/s-4-(4-methyl-
quinolin-2-ylamino)-cyclohexyl]-urea hydrochloride (421 mg, 68%) as a white solid.
ESI MS m/e 465, M (free) + Na+ ; 'HNMR (300 MHz, CDC13) 5 1.76-2.17 (m, 8 H), 2.70 (s, 3 H),
3.69-4.08 (m, 2 H), 6.65-6.83 (m, 2 H), 6.95-7.17 (m, 2 H), 7.41 (t, J= 8.1 Hz, 1 H), 7.54-7.89 (m,
4 H), 8.05-8.17 (m, 1 H), 9.13-9.27 (m, I H).
Example 3073
3-Chloro-/V-[c/s-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 3-chloro-Ar-[c«-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-benzamide
hydrochloride.
To a solution of Af-(c/s-4-methyl-quinolin-2-yl)-cyclohexane-l,4-diamine obtained in step A
of example 3070 (300 mg, 1.17 mmol) in CHC13 (3 mL) were added Et3N (0.35 mL, 2.51 mmol) and
3-chloro-benzoyl chloride (226 mg, 1.29 mmol). The mixture was stirred at ambient temperature for
1.5 hr. The reaction was quenched with saturated aqueous NaHCO3 and the aqueous layer was
extracted with CHC13 (three times). The combined organic layer was dried over MgSO4, filtered,
concentrated, and purified by medium-pressure liquid chromatography (NH-silica gel, 20% to 50%
EtOAc in hexane). To a solution of the above material in EtOAc (2 mL) was added 4 M hydrogen
chloride in EtOAc (lOmL). The mixture was stirred at ambient temperature for 1 hr, and concentrated.
The residue was suspended in Et?O (20 mL) and the suspension was stirred at ambient temperature

646
for 2 hr. The precipitate was collected by filtration, washed with Et?O, and dried at 80 °C under
reduced pressure to give 3-chIoro-A/'-[c/.s-4-(4-methyI-quinolin-2-yIamino)-cyclohexyI]-benzamide
hydrochloride (441 mg, 87%) as a white solid.
ESI MS m/e 416, M (free) + Na+ ; 'H NMR (300 MHz, CDC13) 5 1.78-2.11 (m, 8 H), 2.72 (s, 3 H),
3.92-4.29 (m, 2 H), 6.78 (s, 1 H), 6.94 (d, J= 9.0 Hz, 1 H), 7.33-7.50 (m, 3 H), 7.68-7.76 (m, 3 H),
7.83-7.88 (m, 2 H), 9.58 (d, J- 9.0 Hz, 1 H).
Example 3074
5-Nitro-thiophene-3-carboxylic acid [e/s-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-amide
hydrochloride
Step A: Synthesis of 5-nitro-thiophene-3-carboxylic acid [ci5-4-(4-methyl-quinolin-2-
y1amino)-cyclohexyl]-amide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 411, M(free) + H+ ; lH NMR (300 MHz, CDCI3) 6 1.78-2.14 (m, 8 H), 2.73 (s, 3 H),
3.97-4.26 (m, 2 H), 6.79 (s, 1 H), 7.41-7.57 (m, 2 H), 7.68-7.76 (m, 2 H), 7.85 (d, J= 8.2 Hz, 1 H),
8.26 (d, J= 1.4 Hz, 1H), 8.38 (d, 7= 1.4 Hz, 1 H),9.41 (d, 7= 9.0 Hz, 1 H).
Example 3075
3-Methyl-AL[c/s-4-(4-methyI-quinolin-2-ylamino)-cyclohexylj-benzamide hydrochloride
Step A: Synthesis of 3-methyl-iV-[c*s-4-(4-methyl-quinoIm-2-ylamino)--cyclohexyl]-benzamide
hydrochloride.
Using the procedure for the step B of example 3070, the title compound was obtained.
ESIMSm/e374,M(free) + H+;lHNMR(300MHz,CDCl3)5 1.66-2.10 (m, 8 H), 2.41 (s, 3 H), 2.72
(d,7 = 0.8 Hz, 3 H), 3.94-4.05 (m, 1 H), 4.08-4.25 (m, 1 H), 6.62 (d, 7= 8.1 Hz, 1 H), 6.78 (s, 1 H),

647
7.28-7.36 (m, 2 H), 7.42-7.49 (m, 1 H), 7.58-7.66 (m, 2 H), 7.67-7.79 (m, 2 H), 7.84 (d, J = 8.1 Hz,
1H), 9.62 (d, 7=8.1 Hz, 1 H).
Example 3076
3-Methoxy-Af-[c«-4-(4-methyl-quinolin-2-ylamino)-cyclohexylJ-benzamide hydrochloride
Step A: Synthesis of 3-methoxy-Ar-[tr/$-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzaniide
hydrochloride.
Using the procedure for the step B of example 3070, the title compound was obtained.
ESI MS m/e 390, M(free) + H+ ; lHNMR(300 MHz, CDC13) 5 1.66-2.10 (m, 8 H), 2.72 (s, 3 H), 3.87
(s, 3 H), 3.94-4.26 (m, 2 H), 6.69-6.81 (m, 2 H), 6.99-7.07 (m, 1 H), 7.28-7.51 (m, 4 H), 7.66-7.79 (m,
2 H), 7.84 (d, J= 7.9 Hz, 1 H), 9.55-9.68 (m, 1 H).
Example 3077
4-Cyano-7V-[ci5-4-(4-methyl-quinolin-2-ylamino)-cyclohexylJ-benzamide hydrochloride
Step A: Synthesis of 4-cyano-Ar-[cis-4-(4-methyl'quinolin-2-ylamino)-cyclohexylj-benzamide
hydrochloride.
Using the procedure for the step B of example 3070, the title compound was obtained.
ESI MS m/e 385, M (free) + H+ ; ]H NMR (300 MHz, CDC13) 5 1.79-2.16 (m, 8 H), 2.73 (d, J= 0.9
Hz, 3 H), 3.99-4.29 (m, 2 H), 6.79 (s, 1 H), 7.20-7.28 (m, 1 H), 7.42-7.51 (m, 1 H), 7.69-7.76 (m, 4
H), 7.86 (d, J= 8.2 Hz, 1 H), 7.95-8.02 (m, 2 H), 9.54 (d, J= 8.9 Hz, 1 H).
Example 3078
3,4-Dichloro-Ar-[c«-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-benzamide hydrochloride

648
Step A: Synthesis of 3,4-dichloro-iV-[cw-4-(4-methyl-qiiinolin-2-ylainino)-cyclohexyl]-
ben/amide hydrochloride
Using the procedure for the step B of example 3070, the title compound was obtained.
ESI MS m/e 428, M (free) + H+; lH NMR (300 MHz, CDCI3) 5 1.80-2.14 (m, 8 H), 2.73 (d, J= 0.6
Hz, 3 H), 3.95-4.24 (m, 2 H), 6.75-6.87 (m, 2 H), 7.42-7.52 (m, 2 H), 7.64-7.76 (m, 3 H), 7.85 (d, J
= 8.2 Hz, 1 H),7.98(d,y= 1.9 Hz, 1 H), 9.60 (d, 7= 7.9 Hz, 1 H).
Example 3079
3-Chioro-4-fluoro-7V-[c/5-4-(4-methyl-quinoIin-2-ylaniino)-cyC1-5hexyI]-benzaniide
hydrochloride
Step A: Synthesis of 3-chloro-4-fluoro-jV-{c«-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
benzamide hydrochloride.
Using the procedure for the step B of example 3070, the title compound was obtained.
ESI MS m/e 412, M (free) + H+ ; ]H NMR (300 MHz, CDC13) 5 1.79-2.14 (m, 8 H), 2.73 (d, J= O.i
Hz, 3 H), 3.96-4.26 (m, 2 H), 6.70-6.82 (m, 2 H), 7.18 (t,J= 8.6 Hz, 1 H), 7.42-7.51 (m, 1 H),
7.68-7.78 (m, 3 H), 7.85 (d, 7=8.2 Hz, I H), 7.96 (dd, J = 7.0, 2.2 Hz, 1 H), 9.61 (d,/=8.4Hz, 1
H).
Example 3080
4-Fluoro-3-methyl-iV-[c/5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide
hydrochloride
Step A: Synthesis of 4-fluoro-3-methyI-JV-[cis-4-(4-methyl-quinolin-2-ylaniino)-cyC1-5hexyl]-
benzamide hydrochloride.

649
Using the procedure for the step B of example 3070, the title compound was obtained.
ESI MS m/e 414, M (free) + Na+;'HNMR (300 MHz, CDC13) 5 1.73-2.10 (m, 8 H), 2.33 (d,7= 1.9
Hz, 3 H), 2.72 (s, 3 H), 3.95-4.25 (m, 2 H), 6.45-6.54 (m, 1 H), 6.78 (s, 1 H), 7.00-7.08 (m, 1 H),
7.42-7.50 (m, 1 H), 7.60-7.80 (m, 4 H), 7.84 (d, J= 8.6 Hz, 1 H), 9.58-9.70 (m, 1 H).
Example 3081
l-Methyl-4-nitro-lff-pyrro!e-2-carboxylic acid-[cw-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-amide hydrochloride
Step A: Synthesis of l-methyl-4-nitro~l//-pyrrole-2-carboxylic acid- [c/s-4-(4-methyl-
quinolin-2-ylamino)-cyclohexyl)-amide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 408, M (free) + H+ ; lH NMR (300 MHz, CDC13) 5 1.77-2.11 (m, 8 H), 2.72 (s, 3 H),
3.94-4.14 (m, 5 H), 6.77 (s, 1 H), 7.09-7.16 (m, 1 H), 7.26-7.29 (m, 1 H), 7.41-7.55 (m, 2 H),
7.67-7.78 (m, 2 H), 7.84 (d,J= 8.2 Hz, 1 H), 9.51-9.63 (m, 1 H).
Example 3082
9/?-Xanthene-9-carboxylicacid-[c/s-4-(4-methyI-quinolin-2-ylamino)-cyclohexyI]-amide
hydrochloride
Step A: Synthesis of 9/f-xan then e-9-carboxy lie acid [c/s-4-(4-methyl-quinoIin-2-
ylamino)-cyclohexyl]-amide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 486, M (free) + Na+ ; ]H NMR (300 MHz, CDCI3) 5 1.63-1.91 (m, 8 H), 2.68 (s, 3 H),
3.75-3.97 (m, 2 H), 4.88 (s, 1 H), 6.14-6.27 (m, 1 H), 6.69 (brs, 1 H), 7.03-7.18 (m, 4 H), 7.23-7.49
(m, 5 H), 7.62-7.86 (m, 3 H), 9.34-9.47 (m, I H).

650
Example 3083
5-Bromo-furan-2-carboxylic acid-[c/.y-4-(4-methyl-quinolin-2-yIamino)-cyclohexyl]-
amide hydrochloride
Step A: Synthesis of 5-bromo-furan-2-carboxylic acid [cw-4-(4-methyl-quinolin-2-
ylamino)-cyclohexyl)-amide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 428, M(free) + H+ ; 'H NMR (300 MHz, CDC13) 5 1.62-2.08 (m, 8 H), 2.72 (s, 3 H),
3.90-4.19 (m, 2 H), 6.42 (d, J= 3.6 Hz, 1 H), 6.67-6.80 (m, 2 H), 7.05 (d, J= 3.6 Hz, 1 H), 7.41-7.51
(m, 1 H), 7.67-7.81 (m, 2 H), 7.85 (d,J= 8-4 Hz, 1 H), 9.59-9.72 (m, 1 H).
Example 3084
Ar-[e/$-4-(4-Methyl-quinoIin-2-ylamino)-cyclohexyl]-2-/w-tolyloxy-acetamide hydrochloride
Step A: Synthesis of AL[c/s-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-2-m-tolyloxy-
acetamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 426, M (free) + Na+ ; 'H NMR (300 MHz, CDC13) 8 1.75-2.07 (m, 8 H), 2.34 (s, 3 H),
2.72 (s, 3 H), 3.86-4.14 (m, 2 H), 4.46 (s, 2 H), 6.70-6.95 (m, 5 H), 7.15-7.24 (m, 1 H), 7.41-7.50 (m,
1 H), 7.67-7.88 (m, 3 H), 9.58-9.69 (m, 1 H).
Example 3085
Benzo[2,lT3]oxadiazole-5-carboxylicacid-[cw-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
amide hydrochloride

651
Step A: Synthesis of benzo[2,l>3]oxadiazole-5-carboxylic acid (c/s-4-(4-methyl-quinolin-
2-ylamino)-cycJohexyl]-amide hydrochloride.
Using the procedure for the step A of example 3073, the title compound was obtained.
ESI MS m/e 402, M (free) + H* ; 'HNMR (300 MHz, CDC13) 5 1.79-2.28 (m, 8 H), 2.73 (s, 3 H),
3.98-4.11 (m, 1 H), 4.12-4.32 (m, 1 H), 6.79 (s, 1 H), 7.37-7.50 (m, 2 H), 7.71 (s, 1 H), 7.72 (s, 1 H),
7.81-7.96 (m, 3 H), 8.40 (s, 1 H), 9.56 (d, J= 8.7 Hz, 1 H).
Example 3086
3-Bromo-Ar-[c«-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 3-bromo-AT-[c/s-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-
benzamide hydrochloride.
Using the procedure for the step A of example 3073, the title compound was obtained.
ESI MS m/e 438, M (free) + H+ ; *H NMR (300 MHz, CDC13) 5 1.81-2.13 (m, 8 H), 2.72 (s, 3 H),
3.96-4.06 (m, 1 H), 4.08-4.26 (m, 1 H), 6.75-6.85 (m, 2 H), 7.26-7.34 (m, 1 H), 7.42-7.50 (m, 1 H),
7.57-7.64 (m, 1 H), 7.66-7.79 (m, 3 H), 7.85 (d, J= 8.2 Hz, 1 H), 8.01 (s, 1 H), 9.55-9.66 (m, 1 H).
Example 3087
3-Cyano-Ar-[c/$-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 3-cyano-JV-[cw-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
benzamide hydrochloride.
Using the procedure for the step A of example 3073, the title compound was obtained.
ESI MS m/e 385, M (free) + H+ ; !H NMR (300 MHz, CDC13) 6 1.81-2.18 (m, 8 H), 2.73 (s, 3 H),
3.98-4.29 (m, 2 H), 6.80 (s, I H), 7.13-7.22 (m, 1 H), 7.43-7.60 (m, 2 H), 7.68-7.79 (m, 3 H), 7.85 (d,

652
J= 8.1 Hz, 1 H), 8.08 (d, J= 12 Hz, 1 H), 8.22 (s, 1 H), 9.49-9.62 (m, 1 H).
Example 3088
Ar-[ci5-4-(4-Methyl-quinolin-2-ylamino)-cyclohexyl]-3-trifluoromethyl-benzainide
hydrochloride
Step A: Synthesis of Ar-[c/y-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-3-trifluoromethyl-
benzamide hydrochloride.
Using the procedure for the step A of example 3073, the title compound was obtained.
ESI MS m/e 428, M(free) + Yf; *H NMR (300 MHz, CDC13) 5 1.81-2.14 (m, 8 H), 2.73 (s, 3 H),
3.95-4.09 (m, 1 H), 4.12-4.31 (m, 1 H), 6.79 (s, 1 H), 6.85-6.99 (m, 1 H), 7.43-7.50 (m, 1 H), 7.57 (t,
.7=7.8 Hz, 1 H), 7.64-7.79 (m, 3 H), 7.85 (d,J= 8.2 Hz, 1 H), 8.01 (d, 7= 7.8 Hz, 1 H), 8.15 (s, 1
H), 9.56-9.68 (m, I H).
Example 3089
Ar-[cw-4-(4-MethyI-quinolin-2-ylamino)-cyclohexyl]-2,2-diphenyl-acetamide hydrochloride
Step A: Synthesis of A^c/M-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-2,2-diphenyl-
acetamide hydrochloride.
Using the procedure for the step A of example 3073, the title compound was obtained.
ESI MS m/e 472, M(free) + Na+ ; 'H NMR (300 MHz, CDC13) 5 1.56-2.10 (m, 8 H), 2.51-2.87 (m,
3 H), 3.81-4.16 (m, 2 H), 4.94 (s, 1 H), 6.40-6.88 (m, 2 H), 7.17-7.51 (m, 11 H), 7.63-7.89 (m, 3 H),
9.44 (brs, 1 H).
Example 3090

653
2-(4-riuoro-pheno\y)-A^-[cw-4-(4-methyl-quinolin-2-yIamino)-cyclohexyI]-nicotinamide
hydrochloride
Step A: Synthesis of 2-(4-fluoro-phenoxy)-Ar-[cw-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-
nicotinamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 493, M (free) + Na+ ; 'H NMR (300 MHz, CDC13) 5 1.85-2.12 (m, 8 H), 2.71 (s, 3 H),
3.87-4.00 (m, 1 H), 4.11-4.30 (m, 1 H), 6.76 (brs, 1 H), 7.09-7.21 (m, 3 H), 7.24-7.35 (m, 2 H), 7.44
(t,J=7A Hz, 1 H), 7.65-7.99 (m, 4 H), 8.19-8.25 (m, 1 H), 8.54 (d, 7-6.2 Hz, 1 H), 9.60-9.73 (m,
1H).
Example 3091
2-(3,4-Difluoro-phenoxy)-iV-[c«-4-(4-methyl-quinolin-2-ylamino)-cyclohexylj-nicotinamide
hydrochloride
Step A: Synthesis of 2-(3,4-difluoro-phenoxy)-Ar-[cis-4-(4-methyl-quinolin-2-ylamino)-
cyclohexylj-nicotinamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 511, M(free) + Na+;1H NMR (300 MHz, CDC13) 5 1.81-2.13 (m, 8 H), 2.71 (s, 3 H),
3.90-4.03 (m, 1 H), 4.13-4.30 (m, 1 H), 6.76 (s, 1 H), 7.10-7.51 (m, 5 H), 7.65-7.88 (m, 4 H),
8.18-8.27 (m, 1 H), 8.50-8.58 (m, 1 H), 9.67-9.81 (m, 1 H).
Example 3092
N-[cis-4-(4-Methyl-quinolin-2-ylamino)-cyclohexylj-2-^-tolyloxy-nicotinamide hydrochloride
Step A: Synthesis of iV-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-2-p-toIyloxy-

654
nicotinamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 489, M (free) + Na+ ; ]HNMR (300 MHz, CDC13) 5 1.83-2.15 (m, 8 H), 2.36 (s, 3 H),
2.71 (s, 3 H), 3.78-4.03 (m, 1 H), 4.10-4.32 (m, 1 H), 6.67-6.84 (m, 1 H), 7.06-7.51 (m, 6 H),
7.62-7.90 (m5 3 H), 7.95-8.08 (m, 1 H), 8.19-8.30 (m, 1 H), 8.48-8.61 (m, I H), 9.62 (brs, 1 H).
Example 3093
2-(4-Chloro-phenoxy)-Ar-[c/s-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-iiicotinaniide
hydrochloride
Step A: Synthesis of 2-(4-chloro-phenoxy)-A^cw-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-
nicotinamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 487, M (free) + H+ ; ]H NMR (300 MHz, CDCI3) 5 1.58-2.13 (m, 8 H), 2.71 (s, 3 H),
3.87-4.02 (m, 1 H), 4.10-4.31 (m, 1 H), 6.75 (brs, 1 H), 7.15 (dd, J= 7.5, 4.8 Hz, 1 H), 7.22-7.33 (m,
2 H), 7.37-7.49 (m, 3 H), 7.64-7.92 (m, 4 H), 8.21 (dd, J= 4.8, 2.0 Hz, 1 H), 8.53 (dd, J= 1,6, 2.0
Hz, 1 H), 9.63-9.78 (m, 1 H).
Example 3094
2-(4-Bromo-phenoxy)-N-[ci$-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide
hydrochloride
Step A: Synthesis of 2-(4-bromo-phenoxy)-J/V-[c«-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
nicotinamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 531, M (free) + rT ; 'HNMR (300 MHz, CDC13) 5 1.81-2.20 (m, 8 H), 2.72 (s, 3 H),

655
3.83-4.31 (m, 2 H), 6.66-6.85 (m, I H), 7.03-7.93 (m, 10 H), 8.16-8.28 (m, 1 H), 8.46-8.61 (m, 1 H),
9.55-9.61 (m, 1 H).
Example 3095
2-(4-Methoxy-phenoxy)-A':-[c/s-4-(4-inethyl-quinolin-2-ylainino)-cyC1-5hexyl]-nicotinaniide
hydrochloride
Step A: Synthesis of 2-(4-methoxy-phenoxy)-7V-[ci!y-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-nico tin amide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 483, M(free) + H+ ; 'HNMR (300 MHz, CDC13) 5 1.84-2.19 (m, 8 H), 2.71 (s, 3 H),
3.74-4.00 (m, 4 H), 4.12-4.28 (m, 1 H), 6.68-6.82 (m, 1 H), 6.91-7.30 (m, 5 H), 7.38-7.50 (m, 1 H),
7.63-7.88 (m, 3 H), 7.96-8.09 (m, 1 H), 8.17-8.33 (m, 1 H), 8.48-8.61 (m, 1 H), 9.50-9.70 (m, 1 H).
Example 3096
2-(3-Chloro-4-fluoro-phenoxy)-iV-[c/5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
nicotinamide hydrochloride
Step A: Synthesis of 2-(3-chloro-4-fluoro-phenoxy)-A'-[c«-4-(4-methyl-quinolin-2-ylamino)-
cyclohexylj-nicotinamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 505, M (free) + HVH NMR (300 MHz, CDC13) 5 1.67-2.13 (m, 8 H), 2.71 (s, 3 H),
3.89-4.02 (m, 1 H), 4.13-4.29 (m, I H), 6.76 (brs, 1 H), 7.17 (dd, J= 7.6, 4.8 Hz, 1 H), 7.22-7.49 (m,
4 H), 7.65-7.87 (m, 4 H), 8.21 (dd,7=4.8,2.0 Hz, 1 H), 8.52 (dd,/= 7.6, 2.0 Hz, 1 H), 9.65-9.77 (m,
1H).

656
Example 3097
Ar-[c/s-4-(4-Methyl-quinonn-2-ylamino)-cyclohexyl]-2-ffi-tolyloxy-nicotinamide hydrochloride
Step A: Synthesis of 7V-[c&-4-(4-Methyl~quinolin-2-ylamino)-cyclohexyl]-2-m-tolyloxy-
nicotinamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESIMSm/e467,M(free) + H+;1HNMR(3OOMHz,CDCl3)81.85-2.1O(m,8H),2.4O(s,3H),2.7O
(s, 3 H), 3.84-3.98 (m, 1 H), 4.10-4.24 (m, 1 H), 6.76 (brs, 1 H), 7.00-7.21 (m, 4 H)5 7.28-7.48 (m, 2
H), 7.62-7.87 (m, 3 H), 7.94-8.06 (m, 1 H), 8.21-8.29 (m, 1 H), 8.53 (d, J= 6.4 Hz, 1 H), 9.51-9.64
(m, 1 H).
Example 3098
2-(3-Methoxy-phenoxy)-iV-[C1-5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-acetamide
hydrochloride
Step A: Synthesis of 2-(3-methoxy-phenoxy)-W-[C1-5-4-(4-methyl-quinolin-2-ylamino)-
cyclohexylj-acetamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 442, M (free) + Na+ ; ]H NMR (300 MHz, CDC13) 5 1.71-2.06 (m, 8 H), 2.72 (s, 3 H),
3.82 (s, 3 H), 3.89-4.11 (m, 2 H), 4.46 (s, 3 H), 6.52-6.61 (m, 3 H), 6.75 (s, 1 H) 6.84-6.92 (m, 1 H),
7.16-7.24 (m, 1 H), 7.41-7.49 (m, 1 H), 7.67-7.80 (m, 1 H), 7.84 (d, 7= 8.2 Hz, 1 H), 9.57-9.70 (m,
1H).
Example 3099
2-(3-Chloro-phenoxy)-A^-[c/5-4-(4-methyl-quinolin-2-ylamino)-cyc!lohexyl]-acetamide

657
hydrochloride
Step A: Synthesis of 2-(3-chloro-phenoxy)-Ar-[c/s-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
acetamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 446, M (free) + Na+ ; !H NMR (300 MHz, CDCI3) 5 1.80-2.06 (m, 8 H), 2.72 (s, 3 H),
3.91-4.13 (m, 2 H), 4.45 (s, 2 H), 6.73-7.03 (m, 5 H), 7.19-7.28 (m, 1 H), 7.41-7.50 (m, 1 H),
7.67-7.87 (m, 3 H), 9.58-9.72 (m, 1 H).
Example 3100
2-(3-Chloro-4-fluoro-phenoxy)-7V-[c/$-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
acetamide hydrochloride
Step A: Synthesis of 2-(3-chloro-4-fluoro-phenoxy)-iV-[m-4-(4-methyl-quinolin-2-
ylamino)-cyclohexyl]-acetamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 464, M(free) + Na+ ; !HNMR (300 MHz, CDC13) 8 1.70-2.07 (m, 8 H), 2.72 (s, 3 H),
3.91-4.14 (m, 2 H), 4.42 (s, 2 H), 6.76 (s, I H), 6.83-6.95 (m, 2 H), 6.99-7.16 (m, 2 H), 7.42-7.50 (m,
1 H), 7.67-7.80 (m, 2 H), 7.84 (d, J= 7.9 Hz, 1 H), 9.59-9.70 (m, 1 H).
Example 3101
2-(3,4-Dichloro-phenoxy)-iV-[c«-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-acetamide
hydrochloride
Step A: Synthesis of 2-(3,4-dichIoro-phenoxy)-A^-[c/s-4-(4-methyl-quinolin-2-yIamino)-
cyclohexyl]-acetamide hydrochloride.

658
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 480, M (free) + Na+; *H NMR (300 MHz, CDC13) 5 1.78-2.13 (m, 8 H), 2.72 (s, 3 H),
3.91-4.14 (m, 2 H), 4.44 (s, 2 H), 6.76 (brs, 1 H), 6.84-6.93 (m, 2 H), 7.09 (d, J= 2.8 Hz, 1 H), 7.37
(d, J= 8.9 Hz, 1 H), 7.42-7.49 (m, 1 H), 7.67-7.80 (m, 2 H), 7.84 (d, J= 8.1 Hz, 1 H), 9.54-9.72 (m,
1H).
Example 3102
C-(MethyI-phenyl-amino)-7V-[c/s-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-acetainide
dihydrochloride
Step A: Synthesis of C-(methyl-phenyl-amino)-Ar-[cw-4-(4-methyl-quinolin-2-ylamino)-
cyclohexylj-acetamide dihydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 403, M(free) + H+ ; ]H NMR (300 MHz, CDC13) 8 1.67-1.99 (m, 8 H), 2.70 (s, 3 H), 3.11
(s, 3 H), 3.76-4.06 (m, 4 H), 6.63-7.01 (m, 4 H), 7.08-7.50 (m, 4 H), 7.60-7.92 (m, 3 H), 9.34-9.51 (m,
1H).
Example 3103
2-(3,4-Dichloro-phenyIamino)-7V-[c/$-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-acetamide
dihydrochloride
Step A: Synthesis of 2-(3,4-dichloro-phenylamino)-Ar-[c/s-4-(4-methyI-quinolin-2-ylamino)-
cyclohexylj-acetamide dihydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 479, M (free) + Na+ ; lH NMR (300 MHz, CDC13) 5 1.75-2.02 (m, 8 H), 2.71 (s, 3 H),
3.74-4.08 (m, 4 H), 6.45-6.56 (m, 1 H), 6.67-6.78 (m, 2 H), 7.04-7.19 (m, 2 H), 7.39-7.50 (m, 1 H),

659
7.62-7.87 (m, 3 H), 9.31-9.46 (m, 1 H).
Example 3104
3,4-Difluoro-Ar-[c/5-4-(4-methyl-quinolin-2-yIamino)-cyclohexylmethy1]-benzamide
hydrochloride
Step A: Synthesis of (c«-4-aminomethyl-cyclohexyl)-(4-methyl-quinolin-2-yl)-amine.
A mixture of 2-chIoro-4-methyI-quinoline (10.0 g, 56.3 mmol) and (cis-4-amino-
cyclohexylmethyl)-carbamic acid benzyl ester obtained in step C of example 3068 (17.7 g, 67.6
mmol) in butanol (10 mL) was stirred at reflux for 5 days. The reaction mixture was poured into
saturated aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (three times). The
combined organic layer was dried over MgSC>4, filtrated, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica gel, 10% to 20% EtOAc in hexane and silica gel,
2% to 10% MeOH in CHC!3) to give a pale yellow oil. To a solution of the above oil in MeOH (140
mL) was added 10% Pd/C (1.40 g). The mixture was stirred at ambient temperature under hydrogen
atmosphere for 6 days. The reaction mixture was filtrated through a pad of celite, concentrated, and
purified by medium-pressure liquid chromatography (NH-silica gel, 2% to 10% MeOH in CHC13) to
give (c/5-4-aminomethyl-cyclohexy!)-(4-methyl-quinolin-2-yl)-amine (5.74 g, 38%) as a pale yellow
solid.
ESI MS m/e 470, M+ H+;]HNMR (300 MHz, CDC13)81.14-1.51 (m, 4 H), 1.60-1.94 (m, 5 H), 2.56
(s, 3 H), 2.60 (d, J= 6.4 Hz, 2 H), 4.08-4.22 (m, 1 H), 4.82-4.92 (m, 1 H), 6.52 (s, 1 H), 7.17-7.24 (m,
1 H), 7.47-7.54 (m, 1 H), 7.62-7.67 (m, 1 H), 7.72-7.77 (m, 1 H).
Step B: Synthesis of 3,4-difluoro-A'-[cw-4-(4-methyl-quinolin-2-ylamino)-cyclohexylmethyl]-
benzamide hydrochloride.
To a solution of (cw-4-aminomethyl-cyclohexyl)-(4-methyl-quinolin-2-yl)-amine (300 mg,
0.90 mmol) in CHC13 (2 mL) were added i-Pr2NEt (0.33 mL, 1.89 mmol) and 3,4-difluoro-benzoyl

660
chloride (175 mg, 0.99 mmol) in CHCI3 (1 mL). The mixture was stirred at ambient temperature for
6 hr. The reaction was quenched with saturated aqueous NaHCO3 and the aqueous layer was extracted
with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated,
and purified by medium-pressure liquid chromatography (NH-silica gel, 20% to 25% EtOAc in
hexane) to give a colorless oil. To a solution of the above material in EtOAc (10 mL) was added 4
M hydrogen chloride in EtOAc (0.2 mL). The mixture was stirred at ambient temperature for 1 hr and
concentrated. The residue was suspended in Et2O (20 mL) and the suspension was stirred at ambient
temperature for 2 hr. The precipitate was collected by filtration, washed with Et2O, and dried at 60 °C
under reduced pressure to give 3,4-dif]uoro-iV-[cjs-4-(4-methyl-quinolin-2-yIamino)-
cyclohexylmethylj-benzamide hydrochloride (289 mg, 72%) as a white solid.
ESI MS m/e 432, M(free) + Na+ ; 'H NMR (300 MHz, CDC13) 6 1.56-2.05 (m, 9 H), 2.70 (s, 3 H),
3.49-3.54 (m, 2 H), 3.97-4.09 (m, 1 H), 6.75 (s, 1 H), 6.89-6.98 (m, 1 H), 7.19-7.30 (m, 1 H),
7.40-7.47 (m, 1 H), 7.66-7.75 (m, 2 H), 7.79-7.93 (m, 3 H), 9.72-9.85 (m, 1 H).
Example 3105
Ar-|c/5-4-(4-Methyl-quinolin-2-ylamino)-cyclohexylmethyl]-2-phenoxy-iiicotinamide
hydrochloride
Step A: Synthesis of iV-[c«-4-(4-methyl-quinoIin-2-ylamino)-cyC1-5hexylmethyI]-2-
phenoxy-nicotinamide hydrochloride.
Using the procedure for the step C of example 3104, the title compound was obtained.
ESI MS m/e 467, M(free) + H+ ; ]H NMR (300 MHz, CDC13) 5 1.61-2.14 (m, 9 H), 2.69 (s, 3 H),
3.42-3.50 (m, 2 H), 3.92-4.04 (m, I H), 6.73 (brs, 1 H), 7.10-7.32 (m, 4 H), 7.38-7.49 (m, 3 H),
7.64-7.84 (m, 3 H), 8.06-8.15 (m, I H), 8.19-8.24 (m, 1 H), 8.57-8.63 (m, 1 H), 9.49-9.62 (m, 1 H).
Example 3106

661
l-(23-Dichloro-phenyl)-3-[c/s-4-(4-methyI-quinolin-2-ylamino)-cyclohexylmethyl]-urea
hydrochloride
Step A: Synthesis of l-(2,3-dichIoro-phenyl)-3-[cw-4-(4-methyl-quinolin-2-ylamino)-
cyclohexylmethyl]-urea hydrochloride.
To a solution of (c^-4-aminomethyI-cyclohexyI)-(4-methyl-quinolin-2-yl)-amine obtained in
step B of example 3014 (300 mg, 1.11 mmol) in DMSO (3 mL) was added
l,2-dichloro-3-isocyanato-benzene (230 mg, 1.22 mmol). The mixture was stirred at ambient
temperature for 21 hr and poured into water (20 mL). The precipitate was collected by filtration,
washed with water, and purified by medium-pressure liquid chromatography (NH-silica gel, 20%
EtOAc in hexane) to give a pale yellow oil. To a solution of the above material in EtOAc (10 mL) was
added 4 M hydrogen chloride in EtOAc (0.2 mL). The mixture was stirred at ambient temperature for
1 hr and concentrated. A suspension of the residue in Et2O (20 mL) was stirred at ambient tempareture
for 1 hr. The precipitate was collected by filtration, washed with Et2O, and dried at 60 °C under
reduced pressure to give l-(2,3-dichloro-phenyI)-3-[c/s-4-(4-methyl-quinolin-2-yIamino)-
cyclohexylmethyl]-urea hydrochloride (247 mg, 45%) as a white solid.
ESI MS m/e 479, M (free) + Na+ ; ]HNMR (300 MHz, CDC13) 5 1.51-2.18 (m, 9 H), 2.71 (d,J= 0.8
Hz, 3 H), 3.37-3.44 (m, 2 H), 4.04-4.14 (m, 1 H), 6.78 (s, 1 H), 6.89-7.13 (m, 3 H), 7.42-7.50 (m, 1
H), 7.70-7.76 (m, 2 H), 7.84 (d, J= 8.1 Hz, 1 H), 8.13-8.22 (m, 2 H), 9.38 (d, J= 9.2 Hz, 1 H), 13.95
(brs, I H).
Example 3107
^-[c/s^-t^Dimethylamino-S^^jS-tetrahydro-ciuinazoHn^-ylaminoJ-cyclohexyll^-phenoxy-
nicotinamide hydrochloride
Step A: Synthesis of 5,6,7,8-tetrahydro-quinazoline-2,4-dioI.
To a solution of 2-oxo-cyclohexanecarboxy!ic acid ethyl ester (61.5 g, 361 mmol) in EtOH

662
(61.5 mL) was added urea (73.8 g, 1.23 mol). The mixture was stirred at reflux for 10.5 days and
stirred at ambient temperature for 30 min. The precipitate was filtrated, washed with acetone, and
dried. A suspension of the above solid in H2O(100 mL) stirred on an ice-bath for I hr. The precipitate
was filtrated, washed with hexane, and dried under reduced pressure to give
5,6,7,8-tetrahydro-quinazoline-2,4-diol (21.0 g, 35%) as a pale yellow solid.
CI MS m/e 167, M + H+ ; !H NMR (300 MHz, DMSO-d6) 5 1.48-1.71 (m, 4 H), 2.09-2.19 (m, 2 H),
2.24-2.34 (m, 2 H), 10.41-10.98 (m, 2 H).
Step B: Synthesis of (2-chloro-5,6,7,8-tetrahydro-quinazoIin-4-yl)-dimethyl-amine.
A suspension of 5,6,7,8-tetrahydro-quinazoline-2,4-diot (20.9 g, 100 mmol) in POC13 (105
mL) was stirred at reflux for 2 hr and the reaction mixture was concentrated. The residue was poured
into ice water. The aqueous layer was extracted with EtOAc (three times). The combined organic
layer was dried over MgSO4, filtrated, and concentrated. To the solution of residue (7.00 g) in THF
(70 mL) was added 50% aqueous Me2NH (7.77 g, 86.2 mmol) and the mixture stirred at ambient
temperature for 2 hr. To the reaction was added saturated aqueous NaHCO3 and the aqueous layer was
extracted with CHC13 (three times). The combined organic layer was dried over MgSO4, filtered,
concentrated, and purified flash chromatography (silica gel, 20% EtOAc in hexane) to give
(2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yl)-dimethyI-amine (6.08 g, 64%) as a white solid.
ESI MS m/e 234, M + Na+ ; 'H NMR (300 MHz, CDC13) 5 1.62-1.90 (m, 4 H), 2.59 (t, J= 6.0 Hz, 2
H), 2.76 (t, J= 6.6 Hz, 2 H), 3.06 (s, 6 H).
Step C: Synthesis of (cw-4-amino-cyclohexyl)-carbamic acid benzyl ester.
To a solution of (c«-4-arnino-cyclohexyl)-carbamic acid fe/?-butyl ester obtained in step B of
example 3031 (75.0 g, 350 mmol) in CHC13 (750 mL) were added Et3N (53.7 mL, 385 mmol) and
benzyl chloroformate (55 mL, 385 mmol). The mixture was stirred at ambient temperature for 20 hr.
The reaction was quenched with saturated aqueous NaHCO3 and the aqueous layer was extracted
with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated,
purified by flash chromatography (silica gel, 0.4% to 5% MeOH in CHC13) to give a pale yellow oil.

663
To a solution of the residue in EtOAc (200 mL) was added 4 M hydrogen chloride in EtOAc (200
mL). The mixture was stirred at ambient temperature for 2 hr and concentrated. The residue was
dissolved in 1 M aqueous NaOH and the aqueous layer was extracted with CHCI3 (three time). The
combined organic layer was dried over MgSO4, filtered, concentrated, and purified flash
chromatography (silica gel, 25% to 50% EtOAc in hexane) to give (c/s-4-amino-cyC1-5hexyl)-carbamic
acid benzyl ester (37.6 g? 43%) as a pale brown oil.
ESI MS m/e249, M+ + H+; 'HNMR (200 MHz, CDC13) 5 1.13-1.83 (m, 8 H), 2.77-2.97 (m, 1 H),
3.63-3.83 (m, 1 H), 4.92-5.20 (m, 3 H), 7.25-7.47 (m, 5 H).
Step D: Synthesis of jV2-(cfs-4-aminoM:yC1-5hexyl)-A^^-dimethyl-5,6/7,8-tetrahydro-
quinazoline-2,4-diamine.
A mixture of (2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yl)-dimethyl-amine (16.0 g, 75.7
mmol)and (c/.s-4-amJno-cyclohexyl)-carbamic acid benzyl ester (18.8 g, 75.7 mmol) in butanol (21
mL) was stirred at reflux for 6 days. The reaction mixture was poured into saturated aqueous NaHCO3,
and the aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried
over MgSO4, filtrated, concentrated, and purified by flash chromatography (NH-silica, 33% to 50%
EtOAc in hexane) to give a pale yellow oil. To a solution of the above oil in MeOH (270 mL) was
added 10% Pd/C (2.70 g). The mixture was stirred at ambient temperature under hydrogen
atmosphere for 1.5 days. The reaction mixture was filtrated through a pad of celite, concentrated, and
purified by medium-pressure liquid chromatography (NH-silica gel, 1% to 5% MeOH in CHC13) to
give A^2-(c/5-4-amino-cyclohexyI)-iV4^V4-dimethyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine (15.8 g,
72%) as a pale yellow solid.
FAB MS m/e 290, M+ + H*; !H NMR (200 MHz, CDC13) 5 1.00-1.90 (m, 14 H), 2.49 (t, J= 5.9 Hz,
2 H), 2.61 (t, J= 6.6 Hz, 2 H), 2.71-3.00 (m, 7 H), 3.93-4.07 (m, 1 H), 4.67-4.80 (m, 1 H).
Step E: Synthesis of A^-[m-4-(4-dimethy]amino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-
cyrfohexyl]-2-phenoxy-nicotinamide hydrochloride
To a solution of ^-(c^^-amino-cyclohexylJ-T^/^-dimethyl-S^J^-tetrahydro-

664
quinazoline-2,4-diamine (300 mg, 1.04 mmol) in CHC13 (3 mL) were added Et3N (0.31 mL, 2.22
mmol) and 2-phenoxy-nicotinoyI chloride (266 mg, 1.14 mmol). The mixture was stirred at ambient
temperature for 3 hr. The reaction was quenched with saturated aqueous NaHCOs and the aqueous
layer was extracted with CHC13 (three times). The combined organic layer was dried over MgSO4,
filtered, concentrated, and purified by medium-pressure liquid chromatography (NH-silica gel, 20%
EtOAc in hexane). To a solution of the above material in EtOAc (2 mL) was added 4 M hydrogen
chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated.
The residue was suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature
for 2 hr. The precipitate was collected by filtration, washed with Et2O, and dried at 80 °C under
reduced pressure to give A/-[c/5-4-(4-dimethylamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-
cydohexyl]-2-phenoxy-nicotinamide hydrochloride (159 mg, 29%) as a white solid.
ESI MS m/e 487, M(free) + HVHNMR (300 MHz, CDC13) 5 1.61-1.98 (m, 12 H), 2.54 (t, J= 5.9
Hz, 2 H), 2.74 (t, J= 6.5 Hz, 2 H), 3.20 (s, 6 H), 4.02-4.20 (m, 2 H), 7.12 (dd, J= 7.5, 4.8 Hz, 1 H),
7.21-7.30 (m, 3 H), 7.42-7.50 (m, 2 H), 7.87-7.93 (m, t H), 8.21 (dd, J= 4.8, 2.2 Hz, 1 H), 8.25-8.32
(m, 1 H), 8.52 (dd, .7=7.6, 2.0 Hz, 1 H), 13.18 (s, 1 H).
Example 3108
3-Chloro-Ar-[cw-4-(4-dimethylamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-cyclohexyl]-
4-fluoro-benzamide hydrochloride
Step A: Synthesis of S-chloro-Ar-tcis^-^-dimethylamino-S^^S-tetrahydro-quinazoIin-l-
ylamino)-cyclohexyl]-4-fluoro-benzamide hydrochloride.
Using the procedure for the step E of example 3107, the title compound was obtained.
ESI MS m/e 468, M (free) + Na+ ; lH NMR (300 MHz, CDC13) 5 1.61-2.00 (m, 12 H), 2.51-2.61 (m,
2 H), 2.68-2.81 (m, 2 H), 3.23 (s, 6 H), 4.02-4.26 (m, 2 H), 6.73-6.90 (m, 1 H), 7.13-7.23 (m, 1 H),
7.65-7.82 (m, 1 H), 7.96 (d,J= 6.8 Hz, 1 H), 8.22-8.44 (m, 1 H), 12.63-12.89 (m, 1 H).

665
Example 3109
Ar-[c/5-4-(4-Dimethylamino-5,6,7,8-tetrahydro-quinazoIin-2-ylamino)-cyclohexyl]-4-fluoro-3-
methyl-benzamide hydrochloride
Step A: Synthesis of iV-[c/$-4-(4-dimethylamino-5,6,7,8-tetrahydro-quinazo]in-2-ylamino)-
cyclohexyl]-4-fluoro-3-methyl-benzamide hydrochloride.
Using the procedure for the step £ of example 3107, the title compound was obtained.
ESI MS m/e 448, M (free) + Na+ ; *H NMR (300 MHz, CDCI3) 5 1.60-2.04 (m, 12 H), 2.27-2.36 (m,
3 H), 2.50-2.61 (m, 2 H), 2.65-2.84 (m, 2 H), 3.23 (s, 6 H), 4.03-4.27 (m, 2 H), 6.42-6.58 (m, 1 H),
6.96-7.11 (m, 1 H), 7.56-7.75 (m, 2 H), 8.25-8.47 (m, 1 H).
Example 3110
JV-[cw-4-(4-Dimethylamino-5,6t7,8-tetrahydro-quinazolin-2-ylamino)-cyclohexyl]-3,5-
dimethoxy-benzamide hydrochloride
Step A: Synthesis of A^-[c/$-4-(4-dimethylamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-
cyclohexyl]-3,5-dimethoxy-benzamide hydrochloride.
Using the procedure for the step E of example 3107, the title compound was obtained.
ESI MS m/e 476, M (free) + Na+ ; 'H NMR (300 MHz, CDCI3) 5 1.63-2.04 (m, 12 H), 2.51-2.62 (m,
2 H), 2.66-2.86 (m, 2 H), 3.23 (s, 6 H), 3.85 (s, 6 H), 4.04-4.27 (m, 2 H), 6.50-6.70 (m, 2 H), 6.95 (brs,
2 H), 8.19-8.47 (m, 1 H).
Example 3111
Benzo[2,l,3]oxadiazole-5-carboxylicacid- [as-4-(4-dimethylamino~5,6,7,8-tetrahydro-
quinazolin~2-ylamino)-cyclohexy]]-amide hydrochloride

666
Step A: Synthesis of benzo[2,l,3]oxadiazole-5-carboxylic acid- [m-4-(4-dimethylamino-
5,6,7,8-tetrahydro-quinazoIin-2-ylamino)-cyclohexyl]-amide hydrochloride.
Using the procedure for the step E of example 3107, the title compound was obtained.
ESI MS m/e 458, M (free)+ Na+;'HNMR (300 MHz, CDC13) 5 1.62-2.01 (m, 12 H), 2.56 (t,J= 5.8
Hz, 2 H), 2.71 (t, J- 6.5 Hz, 2 H), 3.23 (s, 6 H), 4.04-4.27 (m, 2 H), 7.71 (d, J= 8.2 Hz, 1 H), 7.85
(dd,J=9.5, 1.1 Hz, 1 H), 7.91-7.96 (m, 1 H), 8.27 (6,J= 8.1 Hz, 1 H), 8.42 (t,J= 1.2 Hz, 1 H).
Example 3112
Ar-[c/y-4-(4-DimethyIamino-5,6,7,8-tetrahydro-quinazolin-2-ylaniino)-cyclohexyll-3-iiitro-
benzamide hydrochloride
Step A: Synthesis of iV-[cw-4-(4-dimethylamino-5,6,7,8-tetrahydro-qiiinazolin-
2-ylamino)-cyC1-5hexyI]-3-nitro-benzamide hydrochloride.
Using the procedure for the step E of example 3107, the title compound was obtained.
ESI MS m/e 461, M(free) + Na+ ; !HNMR (300 MHz, CDC13) 5 1.65-2.04 (m, 12 H), 2.50-2.85 (m,
4 H), 3.24 (s, 6 H), 4.11-4.29 (m, 2 H), 7.04-7.20 (m, 1 H), 7.56-7.68 (m, 1 H), 8.13-8.38 (m, 3 H),
8.72-8.79 (m, 1 H).
Example 3113
7V-[c/5-4-(4-Dimethylamino-5T6,7,8-tetrahydro-quinazolin-2-ylamino)-cyclohexyImethyl]-
2-phenoxy-nicotinamide hydrochloride
Step A: Synthesis of ^-(crs^-aminomethyl-cyclohexyli-A^^V-dimethyl-S^^jS-tetrahydro-
quinazoline-2,4-diamine.
A mixture of (c/s-4-amino-cyclohexylmethyl)-carbamic acid benzyl ester obtained in step C

667
of example 3068 (3.10 g, 11.8 mmol) and (2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yl)-dimethyI-
amine obtained in step B of example 3107 (2.00 g, 9.44 mmol) in butanol (3 mL) was stirred at reflux
for 19 hr. The reaction mixture was poured into saturated aqueous NaHCO3, and the aqueous layer
was extracted with CHC13 (three times). The combined organic layer was dried over MgSO4, filtrated,
concentrated, and purified by flash chromatography (NH-silica gel, 33% to 50% EtOAc in hexane) to
give a pale yellow oil. To a solution of the above oil (2.48 g) in MeOH (25 mL) was added 10% Pd/C
(248 mg). The mixture was stirred at 50 °C under hydrogen atmosphere for 8 hr. The reaction mixture
was filtrated through a pad of celite, concentrated, and purified by medium-pressure liquid
chromatography (NH-silica gel, 1% to 5% MeOH in CHCI3) to give iV2-(c/s-4-aminomethyl-
cyclohexyI)-A^A^-dimethyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine (1.70 g, 59%) as a pale
yellow solid.
FAB MS m/e 304, M (free) + H+
Step B: Synthesis of 7V-[cw-4~(4-dimethylamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-
cyclohexylmethyl]-2-phenoxy-nicotinamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 501, M (free) + H+
Example 3114
A^-[cw-4-(4-DimethyIamino-quinoHn-2-yIamino)-cyclohexyl]-2-phenoxy-nicotinamide
hydrochloride
Step A: Synthesis of 2,4-dichloro-quinoline.
A suspension of quinoline-2r4-dk>l (150 g, 931 mmol) in POC13 (975 mL, 10.4 mol) was
stirred at reflux for 6 hr and the reaction mixture was concentrated. The residue was diluted with
CHCI3 (500 mL) and the solution was poured into ice water. The aqueous layer was extracted with
CHCI3 (three times). The combined organic layer was dried over MgSO4, filtrated, concentrated, and
purified by flash chromatography (silica gel, 20% EtOAc in hexane) to give 2,4-dichloro-quinoline

668
(177 g, 96%) as a pale brown solid.
El MS m/e 197, M+; *H NMR (300 MHz, CDC13) 5 7.50 (s, 1 H), 7.65 (ddd, J= 8.3, 7.0, 1.3 Hz, 1
H), 7.79 (ddd,J= 8.5, 7.0, 1.3 Hz, 1 H), 8.00-8.06 (m, 1 H), 8.16-8.21 (m, 1 H).
Step B: Synthesis of (2-chloro-quinolin-4-yl)-dimethyl-amine.
To a solution of 2,4-dichloro-quinoIine (177 g, 894 mmol) in THF (2.1 L) was added 50%
aqueous Me2NH (234 mL, 2.23 mol). The mixture was stirred at ambient temperature for 68 hr. To
the mixture was added 50% aqueous Me?NH (47 mL, 448 mmol) and stirred at ambient temperature
for 3 hr. The solution was poured into saturated aqueous NaHCO3 and the aqueous layer was
extracted with CHC13 (three times). The combined organic layer was dried over MgSO4, filtrated,
concentrated, and purified by flash chromatography (NH-silica, 1% to 3% EtOAc in hexane) to give
(2-chloro-quinolin-4-yl)-dimethyl-amine (75.9 g, 41%) as a pale yellow oil and (4-chloro-
quinolin-2-yl)-dimethyi-amine (28.0 g, 15%) as a pale yellow oil.
(2-chloro-quinolin-4-yl)-dimethyl-amine;
ESI MS m/e 207, M + H+ ; ]H NMR (300 MHz, CDC13) 5 3.06 (s, 6 H), 6.71 (s, 1 H), 7.45 (ddd, J =
8.4, 7.0, 1.2 Hz, 1 H), 7.63 (ddd, J= 8.4, 6.9, 1.5 Hz, 1 H), 7.91-7.93 (m, 1 H), 7.97-8.03 (m, 1 H).
(4-chloro-quinolin-2-yl)-dirnethyI-amine;
ESI MS m/e 207, M + it;1 H NMR (300 MHz, CDC13) 5 3.18 (s, 6 H), 6.97 (brs, 1 H), 7.18-7.31 (m,
1 H), 7.49-7.63 (m, 1 H), 7.66-7.72 (m, 1 H), 7.95-8.00 (m, 1 H).
Step C: Synthesis of Ar2-(c/5-4-amino-cyclohexyl)-7V4^V4-dimethyl-quinoline-2,4-diamine.
A mixture of (2-chloro-quinolin-4-yl)-dimethyl-amine (15.6 g, 75.7 mmol) and
(c/s-4-amino-cyclohexyl)-carbamic acid benzyl ester obtained in step C of example 3107 (18.8 g,
75.7 mmol) in butanol (20 mL) was stirred at reflux for 6 days. The reaction mixture was poured into
saturated aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (three times). The
combined organic layer was dried over MgSO4, filtrated, concentrated, and purified by flash
chromatography (NH-silica, 33% to 50% EtOAc in hexane) to give a pale yellow oil. To a solution
of the above oil in MeOH (170 mL) was added 10% Pd/C (1.70 g). The mixture was stirred at ambient

669
temperature under hydrogen atmosphere for 1.5 days. The reaction mixture was filtrated through a
pad of celite, concentrated, and purified by medium-pressure liquid chromatography (NH-silica gel,
1 % to 5% MeOH in CHC13) to give A^-(a1y-4'amino-cyclohexyl)-W4,y-dimethyI-quinoIine-
2,4-diamine (11.7 g, 55%) as a pale yellow solid.
FAB MS m/e 285, M + H* ; !HNMR (300 MHz, CDC13) 5 1.19-1.96 (m, 10 H), 2.81-3.03 (m, 7 H),
4.02-4.17 (m, 1 H), 4.66-4.83 (m, 1 H), 6.03 (s, 1 H), 7.06-7.21 (m, 1 H), 7.39-7.52 (tn, 1 H),
7.55-7.67 (m, 1 H), 7.80-7.90 (m, 1 H).
Step D: Synthesis of jV-[cw-4-(4-dimethylamino-quinolin-2-ylamino)-cyclohexyl]-
2-phenoxy-nicotinamide hydrochloride.
To a solution of ^-(cw^-amino-cyclohexy^-A^^-dimethyl-quinoline^^-diamine (300
mg, 1.05 mmol) in CHC13 (3 mL) were added Et3N (0.31 mL, 2.22 mmol) and 2-phenoxy-nicotinoyl
chloride (271 mg, 1.16 mmol). The mixture was stirred at ambient temperature for 3 hr. The reaction
was quenched with saturated aqueous NaHCO3 and the aqueous layer was extracted with CHCI3 (three
times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica gel, 20% EtOAc in hexane). To a solution of the
above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). The mixture
was stirred at ambient temperature for 1 hr and concentrated. The residue was suspended in Et2O (20
mL) and the suspension was stirred at ambient temperature for 2 hr. The precipitate was collected by
filtration, washed with Et2O, and dried at 80 °C under reduced pressure to give N-[cis-4-(4-
dimethylamino-quinolin-2-ylamino)-cyclohexyl]-2-phenoxy-nicotinamide hydrochloride (160 mg,
29%) as a white solid.
ESI MS m/e 482, M (free) + HVH NMR {300 MHz, CDC13) 5 1.57-2.15 (m, 8 H), 3.21 (s, 6 H),
3.73-3.88 (m, 1 H), 4.06-4.27 (m, 1 H), 5.79 (s, 1 H), 7.12 (dd, J= 7.6, 4.8 Hz, 1 H), 7.19-7.33 (m,
4 H), 7.41-7.71 (m, 4 H), 7.81-7.97 (m, 2 H), 8.21 (dd, J= 4.8, 2.0 Hz, 1 H), 8.52 (dd, 7= 7.6, 2.0
Hz, 1 H), 8.94-9.08 (m, 1 H), 13.81 (brs, 1 H).

670
Example 3115
^-[^^-(^Chloro-quinoIin^-ylaminoVcyclohexyll^-phenoxy-nicotinamide hydrochloride
Step A: Synthesis of A^Icw-^^-chloro-quinolin^-ylamiiioJ-cyclohexylJ-^-phenoxy-
nicotinamide hydrochloride.
A mixture of 2,4-dichloro-quinoline obtained in step A of example 3114 (1.5 g, 7.57 mmol)
and JV-(c/s-4-amino-cyclohexyl)-2-phenoxy-nicotinamide obtained in step A of example 2 (2.3 g, 7.57
mmol) in butanol (2 mL) was stirred at 130 °C for 3 days in a sealed tube. The reaction mixture was
poured into saturated aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (three times).
The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica gel, 20% EtOAc in hexane) to give a colorless oil.
To a solution of the above material in EtOAc (10 mL) was added 4 M hydrogen chloride in EtOAc
(0.2 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated. The residue was
suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature for 2 hr. The
precipitate was collected by filtration, washed with Et2O, and dried at 60 °C under reduced pressure to
give A^-[c/5-4-(4-chloro-quinolin-2-ylamino)-cyclohexyl]-2-phenoxy-nicotinamide hydrochloride
(295 mg, 8%) as a white solid and Ar-[c/5-4-(2-chloro-quinolin-4-ylamino)-cyclohexyl]-
2-phenoxy-nicotinamide hydrochloride (283 mg, 7%) as a white solid.
Ar-[c^-4-(4-chloro-quinolin-2-ylamino)-cyclohexyl]-2-phenoxy-nicotinamide hydrochloride;
ESI MS m/e 495, M (free) +Na+ ; ]HNMR (300 MHz, CDC13) 5 1.86-2.10 (m, 8 H), 3.82-3.96 (m,
1 H), 4.13-4.28 (m, 1 H), 7.04 (s, 1 H), 7.10-7.34 (m, 4 H), 7.41-7.55 (m, 3 H), 7.71-7.84 (m, 2 H),
7.92-8.11 (m, 2 H), 8.20-8.26 (m, 1 H), 8.50-8.59 (m, I H), 9.83 (brs, 1 H).
Ar-[c/5-4-(2-chloro-quinolin-4-ylamino)-cyclohexyl]-2-phenoxy-nicotinamide hydrochloride;
ESI MS m/e 495, M (free) + Na+; 'HNMR (300 MHz, DMSO-d6) 5 1.72-2.37 (m, 8 H), 3.64-3.84 (m,
1 H), 4.36 (brs, 1 H), 6.33 (brs, 1 H), 7.05-7.60 (m, 8 H), 8.06-8.66 (m, 6 H).

671
Example 3116
3,4-Difluoro-7V-[m-4-(4-methoxy-quinolin-2-ylamino)-cyclohexyl]-benzaniidehydrochloride
Step A: Synthesis of 2-chloro-quinolin-4-ol.
A mixture of 2,4-dichloro-quinoline obtained in step A of example 3114 (3.00 g, 15.1 mmol)
andMeOH(485 mg, 15.1 mmoi) in butanol (3 mL) was stirred at reflux for 3 hr. The reaction mixture
was suspended in CHC13 (15 mL) and stirred at ambient temperature for 30 min. The precipitate was
collected by filtration, washed with CHC13, and dried at 50 °C under reduced pressure to give
2-chIoro-quinolin-4-ol (1.47 g, 54%) as a pale yellow solid.
ESI MS m/e 179, M+ ; ]H NMR (300 MHz, DMSO-d6) 6 6.83 (s, 1 H), 7.27-7.43 (m, 2 H), 7.60-7.67
(m, 1 H), 7.86 (d, J= 7.9 Hz, 1 H), 12.05 (brs, 1 H).
Step B: Synthesis of 2-chloro-4-methoxy-quinoline.
To a solution of 2-chloro-quinolin-4-oI (500 mg, 2.78 mmol) in DMF (5 mL) were added
K2CO3 (462 mg, 3.37 mmol) and Mel (210 pL, 3.37 mmol). The mixture was stirred at 50°C for 3 hr.
The reaction was quenched with saturated aqueous NaHCO3 and the aqueous layer was extracted
with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated,
and purified by medium-pressure liquid chromatography (NH-silica gel, 10% EtOAc in hexane) to
give 2-chloro-4-methoxy-quinoIine (440 mg, 82%) as a white solid.
ESI MS m/e 194, M + H+ ; ]H NMR (300 MHz, CDC13) 5 3.71 (s, 3 H), 6.89 (s, 1 H), 7.27-7.43 (m,
2 H), 7.60-7.69 (m, 1 H), 8.01 (d,J= 8.1 Hz, 1 H).
Step C: Synthesis of 3,4-difluoro-iV-[c/$-4-(4-methoxy-quinolin-2-ylamino)-cyclohexyI]-
benzamide hydrochloride.
A mixture of 2-chloro-4-methoxy-quinoIine (250 mg, 1.29 mmol) and
7^-(c/5-4-amino-cyclohexyl)-3,4-difluoro-benzamide obtained in step D of example 3031 (361 mg,
1.42 mmol) in butanol (1 mL) was stirred at 130 °C for 5 days in a sealed tube. The reaction mixture
was poured into saturated aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (three

672
times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica gel, 20% to 50% EtOAc in hexane). To a
solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL).
The mixture was stirred at ambient temperature for 1 hr and concentrated. The residue was
suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature for 2 hr. The
precipitate was filtered, washed with Et?O, and dried at 80 °C under reduced pressure to give
c/5-3,4-difluoro-AL[4-(4-methoxy-quinolin-2-ylamino)-cyclohexyl]-benzamide hydrochloride (79 mg,
14%) as a white solid.
ESI MS m/e 434, M (free) + Na+; !H NMR (300 MHz, DMSO-d6) 5 1.58-2.09 (m, 8 H), 3.55-3.72 (m,
4 H), 3.88-4.06 (m, 1 H), 5.93 (s, 1 H), 7.03-8.09 (m, 7 H), 8.25-8.45 (m, 2 H).
Example 3117
Ar-[ci$-4-(4-Chloro-quinolin-2-ylamino)-cyclohexyl]-3,4-difluoro-benzamide hydrochloride
Step A: Synthesis of Ar-[c/s-4-(4-ehIoro-quinolin-2-yIamino)-cyclohexyl]-3,4-dinuoro-
benzamide hydrochloride.
Using the procedure for the step A of example 3115, the title compound was obtained.
A^-fc/^-^-chloro-quinoIin^-ylamino^cyclohexylj-S^-difluoro-benzamide hydrochloride;
ESI MS m/e 416, M (free) + H* ; 'H NMR (300 MHz, CDC13) 5 1.82-2.22 (m, 8 H), 3.93-4.28 (m,
2 H), 6.65-6.77 (m, 1 H), 7.08 (s, I H), 7.14-7.29 (m, 1 H), 7.48-7.64 (m, 2 H), 7.68-7.88 (m, 3 H),
8.09 (d, 7=8.1 Hz, 1 H), 9.82-9.90 (m, 1 H).
7V-[cw-4-(2-chloro-quinolin-4-ylamino)-cyclohexyl]-3,4-difluoro-benzamide hydrochloride;
ESI MS m/e 438, M (free) + Na+; !H NMR (300 MHz, CDC13) 5 1.72-2.37 (m, 8 H), 3.76-3.95 (m,
1 H), 4.49-4.65 (m, 1 H), 6.37 (brs, 1 H), 6.94-7.12 (m, 1 H), 7.18-7.33 (m, 1 H), 7.39-7.55 (m, 1 H),
7.60-7.76 (m, 1 H), 7.85-7.95 (m, 1 H), 8.06-8.20 (m, 2 H), 8.46-8.58 (m, 1 H), 8.70-8.87 (m, 1 H).

673
Example 3118
Ar-[C1-5-4-(4-Dimethylamino-quinolin-2-ylamino)-cyclohexylmethyl]-2-phenoxy-nicotinainide
hydrochloride
Step A: Synthesis of [ctf~4-(4~dimethylaminoH)uinoIin-2-ylamino)-cyclohexylmethyI]-carbamic
acid benzyl ester.
A mixture of (2-chloro-quinolin-4-yl)-dimethyl-amine obtained in step B of example 3114
(23.6 g, 114 mmol) and (c^-4-amino-cyclohexylmethyl)-carbamic acid benzyl ester obtained in step
C of example 3068 (36.0 g, 137 mmol) in butanol (31 mL) was stirred at reflux for 14 days. The
reaction mixture was poured into saturated aqueous NaHCO3, and the aqueous layer was extracted
with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtrated, concentrated,
and purified by flash chromatography (NH-silica, 14% to 66% EtOAc in hexane) to give [cis-
4-(4-dimethylamino-quinolin-2-ylamino)-cyclohexylmethyl]-carbamic acid benzyl ester (19.3 g,
39%) as a pale yellow solid.
ESIMSm/e433JM(free) + H+;IHNMR(200MHz,CDCl3)5 1.12-1.97(m,9H),2.94(s,6H),3.13
(t, J= 6.4 Hz, 2 H), 4.06-4.26 (m, 1 H), 4.62-4.94 (m, 2 H), 5.11 (s, 2 H), 6.04 (s, 1 H), 7.14 (ddd, J
= 8.4, 7.0, 1.3 Hz, 1 H), 7.29-7.40 (m, 5 H), 7.45 (ddd, J= 8.4, 6.8, 1.5 Hz, 1 H), 7.51-1.64 (m, 1 H),
7.84 (dd,J= 8.4, 1.3 Hz, 1 H).
Step B: Synthesis of ^-(C1-5^-aminomethyl-cyclohexylJ-A^^-dimethyl-quinohne^^-diamine.
To a solution of [cw-4-(4-dimethyIamino-quinolin-2-yIamino)-cyC1-5hexylmethyl]-
carbamic acid benzyl ester (19.3 g, 44.6 mmol) in MeOH (200 mL) was added 5% Pd/C (1.93 g). The
mixture was stirred at ambient temperature under hydrogen atmosphere for 6 days. The reaction
mixture was filtrated through a pad of celite and concentrated. To a solution of the residue in
methanol (200 mL) was 10% Pd/C (1.93 g). The mixture was stirred at ambient temperature under
hydrogen atmosphere for 1 day. The reaction mixture was filtrated through a pad of celite,
concentrated, and purified by flash chromatography (silica gel, 5% to 14% 7 M NH3/MeOH in CHC13)
to give ^-(c/i^-aminomethyl-cyclohexyO-A^jA^-dimethyl-quinoline^^-diamine (12.7 g, 95%) as a

674
pale yellow solid.
FAB MS m/e 299, M+ + H+; !H NMR (200 MHz, CDC13) 6 1.08-1.99 (m, 11 H), 2.60 (d, J= 6.2 Hz,
2 H), 2.94 (s, 6 H), 4.04-4.22 (m, 1 H), 4.77-4.93 (m, 1 H), 6.06 (s, 1 H), 7.14 (ddd,J= 8.4, 7.0, 1.3
Hz, 1H), 7.45 (ddd, ,7=8.4, 6.8, 1.5 Hz, 1 H), 7.61 (s, 1 H), 7.84 (dd,/= 8.4, 1.3 Hz, 1 H).
Step C: Synthesis of Ar-[c/5-4-(4-dimethylamino-quinolin-2-ylamino)-cyclohexylmethyl]-
2-phenoxy-nicotinamide hydrochloride.
To a solution of 2-Phenoxy-nicotinic acid (190 mg, 1.20 mmol) and
Ar2-(cz5-4-aminomethyl-cyclohexyl)-jV4;JV4-dimethyl-quinoline-2,4-diamine (300 mg, 1.00 mmol) in
DMF (3 mL) were added Et3N (0.33 mL, 2.40 mmol), HOBt-H2O (230 mg, 1.50 mmol), and
EDC-HC1 (230 g, 1.20 mmol). The reaction mixture was stirred at ambient temperature for 20 hr. To
the reaction mixture was added water (20 mL) and the suspension was stirred at ambient temperature
for 30 min. The precipitated was collected by filtration, washed with H2O, and purified by
medium-pressure liquid chromatography (NH-silica gel, 20% EtOAc in hexane) to give a pale yellow
oil. To a solution of the above material in EtOAc (10 mL) was added 4 M hydrogen chloride in EtOAc
(0.2 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated. The residue was
suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature for 2 hr. The
precipitate was collected by filtration, washed with Et2O, and dried at 60 °C under reduced pressure to
give Ar-[c/5-4-(4-dimethylamino-quinolin-2-ylamino)-cyclohexylmethyl]-2-phenoxy-nicotinamide
hydrochloride (164 mg, 31%) as a white solid.
ESI MS m/e 496, M (free) + H+
Example 3119
A^Ic/s^-t^Dimethylamino-S-methyl-pyrimidiii-Z-ylaininoJ-cyclohexylJ-S^-difluoro-
benzamide hydrochloride
Step A: Synthesis of 2-chloro-4-diniethylamino-5-methyIpyrimidine.

675
To the solution of 2,4-dichioro-5-methylpyrimidine (20.0 g, 123 mmol) in THF (200 mL) was
added 50% aqueous Me?NH (13.3 g, 143 mol) and the mixture was stirred at ambient temperature for
5 days. To the reaction was added saturated aqueous NaHCO3 and the aqueous layer was extracted
with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated,
and purified flash chromatography (NH-silica gel, 2% EtOAc in hexane) to give 2-chloro-4-
dimethylamino-5-methylpyrimidine (19.9 g, 94 %) as a white solid and 4-chloro-2-dimethyIamino-
5-methyIpyrimidine (1.53 g, 7%) as a white solid.
2-chloro-4-dimethylarnino-5-methylpyrimidine;
ESI MS m/e 172, M + H+ ; 'H NMR (300 MHz, CDCI3) 8 2.27 (s, 3 H), 3.15 (s, 6 H), 7.82 (s, 1 H).
4-chloro-2-dimethylamino-5-rnethylpyrimidine;
ESI MS m/e 194, M + Na+; ]H NMR (300 MHz, CDC13) 6 2.14 (s, 3 H), 3.15 (s, 6 H), 8.06 (s, 1 H).
Step B: Synthesis of [cj$-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
carbamic acid tert-butyl ester.
A mixture of 2-chloro-4-dimethylamino-5-methyIpyrimidine (7.00 g, 40.8 mmol) and
(c/5-4-amino-cyclohexy!)-carbamic acid tert-buty\ ester obtained in step B of example 3031 (9.61 g,
44.8 mmol) in butanol (7 mL) was stirred at 130 °C for 26 hr. The reaction mixture was poured into
saturated aqueous NaHCO3 and the aqueous layer was extracted with CHCI3 (three times). The
combined organic layer was dried over MgSO4, filtered, concentrated, and purified by flash
chromatography (NH-silica gel, 3% to 50% EtOAc in hexane) to give [c/s-4-(4-dimethylamino-
5-methyI-pyrimidin-2-ylamino)cyclohexyl]-carbamic acid tert-butyl ester (5.90 g, 42%) as a colorless
oil.
ESI MS m/e 350, M + H+; !HNMR (300 MHz, CDC13) 5 1.40-1.84 (m, 17 H), 2.14 (d, 7- 0.8 Hz,
3 H), 3.02 (s, 6 H), 3.53-3.71 (m, 1 H), 3.85-3.99 (m, 1 H), 4.51-4.64 (m, 1 H), 4.68-4.78 (m, 1 H),
7.66 (s, 1 H).
Step C: Synthesis of A^-(cw-4-amino-cyclohexyl)-5^V4^V4-trimethyI-pyrimidine-2,4-diamine.
A solution of [c/s-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)cyC1-5hexyI]-

676
carbamic acid terf-butyl ester (5.71 g, 16.3 mmol) in EtOAc (60 mL) was cooled on an ice-bath and
4 M hydrogen chloride in EtOAc (120 mL) was added. The mixture was stirred at ambient
temperature for 1.5 hr and concentrated. The residue was dissolved in 1 M aqueous NaOH and the
aqueous layer was extracted with CHCb (three time). The combined organic layer was dried over
MgSC>4, filtered, concentrated, and dried under reduced pressure to give A^-(c/5-4-amino-cyclohexyl)-
5,A^^-trimethyl-pyrimidine-2,4-diamine (3.99 g, 98%) as a pale yellow oil.
ESI MS m/e 250, M + H+ ; lH NMR (300 MHz, CDCI3) 5 1.39-1.91 (m, 8 H), 2.12 (s, 3 H), 2.79-2.97
(m, 1 H), 3.00 (s, 6 H), 3.86-4.05 (m, 1 H), 4.71-4.92 (m, 1 H), 7.66 (s, 1 H).
Step D: Synthesis of A^lcK^-t^dimethylamino-S-methyl-pyrimidin-Z-ylaniinoJ-cyclohexyl]-
3,4-difluoro-benzamidehydrochloride.
To a solution of TV -(cz5-4-amino-cyclohexyl)-5,A^,Ar-trimethyl-pyrimidine-2,4-diamine
(200 mg, 0.80 mmol) in CHC13 (4 mL) were added Et3N (0.25 mL, 1.79 mmol) and
1,3-difluoro-benzoyl chloride (156 mg, 0.88 mmol). The mixture was stirred at ambient temperature
for 22 hr. The reaction was quenched with saturated aqueous NaHCC>3 and the aqueous layer was
extracted with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtered,
concentrated, and purified by medium-pressure liquid chromatography (NH-silica gel, 20% to 50%
EtOAc in hexane and silica gel, 3% MeOH in CHC13). To a solution of the above material in EtOAc
(2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient
temperature for 1 hr, and concentrated. The residue was suspended in Et2O (20 mL) and the
suspension was stirred at ambient temperature for 2 hr. The precipitate was collected by filtration,
washed with Et2O, and dried at 80 °C under reduced pressure to give yV-[c/s-4-(4-dimethylamino-
5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-3,4-difluoro-benzamide hydrochloride (56 mg, 16%) as
a white solid.
ESI MS m/e 412, M (free) + Na+ ; ]H NMR (300 MHz, CDC13) 5 1.64-1.99 (m, 8 H), 2.26 (s, 3 H),
3.30 (s, 6 H), 4.02-4.25 (m, 2 H), 6.65-6.74 (m, 1 H), 7.13-7.26 (m, 2 H), 7.53-7.62 (m, 1 H),
7.67-7.79 (m, 1 H), 8.55-8.65 (m, 1 H).

677
Example 3120
^-[C1-5^-f^Dimethylamino-S-methyl-pyriniidiii^-ylainino^cyclohexylJ^-phenoxy-
nicotinamide hydrochloride
Step A: Synthesis of A^cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
2-phenoxy-nicotinamide hydrochloride.
Using the procedure for the step D of example 3119, the title compound was obtained.
ESI MS m/e 447, M (free) + H+ ; 'H NMR (300 MHz, CDC13) 5 1.64-1.97 (m, 8 H), 2.23 (s, 3 H), 3.28
(s, 6 H), 4.01-4.21 (m, 2 H), 7.13 (dd, J= 7.6, 4.8 Hz, 1 H), 7.19-7.32 (m, 4 H), 7.42-7.52 (m, 2 H),
7.86-7.95 (m, 1 H), 8.21 (dd, J= 4.8, 2.0 Hz, 1 H), 8.39-8.48 (m, 1 H), 8.53 (dd, J= 7.6, 2.0 Hz, 1
H).
Example 3121
AL[c/A-4-(4-Dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-3-methyl-benzamide
hydrochloride
Step A: Synthesis of 7V-[c«-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
3-methyl-benzamide hydrochloride.
Using the procedure for the step D of example 3119, the title compound was obtained.
ESI MS m/e 390, M (free) + Na+ ; 'H NMR (300 MHz, CDC13) 8 1.67-2.01 (m, 8 H), 2.25 (s, 3 H),
2.41 (s, 3 H), 3.30 (s, 6 H), 4.04-4.22 (m, 2 H), 6.41-6.52 (m, 1 H), 7.19-7.34 (m, 3 H), 7.56-7.66 (m,
2 H), 8.53-8.63 (m, 1 H), 13.04 (s, 1 H).
Example 3122
7V-[m-4-(4-Dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-3-methoxy-benzamide

678
hydrochloride
Step A: Synthesis of Af-[cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyI]-
3-methoxy-benzamide hydrochloride.
Using the procedure for the step D of example 3119, the title compound was obtained.
ESI MS m/e 406, M (free) + Na+ ; !H NMR (300 MHz, CDC13) 5 1.66-1.99 (m, 8 H), 2.25 (s, 3 H),
3.30 (s, 6 H), 3.86 (s, 3 H), 4.06-4.23 (m, 2 H), 6.72-6.81 (m, 1 H), 6.98-7.05 (m, 1 H), 7.20-7.43 (m,
4 H), 8.47-8.57 (m,lH),
Example 3123
Ar-[c/s-4-(4-DimethyIamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-2-(4-fluoro-phenoxy)-
nicotinamide hydrochloride
Step A: Synthesis of Ar-(c/5-4-(4-diinethylainino-5-methyl-pyrimidin-2-ylamino)-cyclohexyll-2-
(4-fluoro-phenoxy)-nicotinamide hydrochloride.
To a solution of 4-fluoro-phenoI (317 mg, 2.83 mmol) in DMA (4 mL) was added 60% NaH
in oil (226 mg, 5.56 mmol). The mixture was stirred at ambient temperature for 1 hr. To the mixture
was added 2-chloro-A'r-[ci5-4-(dimethylamino-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
nicotinamide (1.10 g, 2.83 mmol) in DMA (3 mL). The mixture was stirred at 120 °C for 2 hr and the
reaction was quenched with water (60 mL). The aqueous layer was extracted with CHC13 (three times).
The combined organic layer was dried over MgSC>4, filtered, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica gel, 33% to 50% EtOAc in hexane) to give a
colorless oil. To a solution of the above material in EtOAc (10 mL) was added 4 M hydrogen chloride
in EtOAc (0.2 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated. The
residue was suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature for 2
hr. The precipitate was collected by filtration, washed with Et2O, and dried at 60 °C under reduced
pressure to give Ar-[c/5-4-(4-dimethyIamino-5-methyI-pyrimidin-2-ylamino)-cyclohexyl]-2-

679
(4-fluoro-phenoxy)-nicotinamide hydrochloride (154 mg, 11%) as a white solid.
ESI MS m/e 487, M (free) + Na+ ; !H NMR (200 MHz, CDC13) 5 1.61-2.02 (m, 8 H), 2.24 (s, 3 H),
3.28 (s, 6 H), 4.03-4.25 (m, 2 H), 7.06-7.33 (m, 6 H), 7.79-7.91 (m, 1 H), 8.16-8.23 (m, 1 H),
8.46-8.59 (m, 2 H).
Example 3124
2-(2-Bromo-phenoxy)-7V-[c/y-4-(4-dimethyIamino-5-methyl-pyrimidin-2-ylaniino)-
cyclohexylj-nicotinamide hydrochloride
Step A: Synthesis of 2-(2-bromo-phenoxy)-Ar-[c/s-4-(4-dimethylamino-5-methyl-
pyrimidin-2-ylamino)-cydohexyl]-nicotinamide hydrochloride.
Using the procedure for the step A of example 3123, the title compound was obtained.
ESI MS m/e 547, M (free) + Na+ ; !H NMR (200 MHz, CDC13) 5 1.72-2.02 (m, 8 H), 2.23 (s, 3 H),
3.28 (s, 6 H), 3.97-4.27 (m, 2 H), 7.09-7.48 (m, 5 H), 7.66 (dd, J= 7.9, 1.3 Hz, 1 H), 7.84-7.95 (m,
1 H), 8.13-8.19 (m, 1 H), 8.31-8.43 (m, 1 H), 8.53 (6d,J = 7.4, 2.2 Hz, 1 H), 13.32 (s, 1 H).
Example 3125
l-(2r3-Dichloro-phenyl)-3-[c/$-4-(4-dimethylamino-5-inethyl-pyrimidin-2-ylainino)-
cyC1-5hexylmethyl]-urea hydrochloride
Step A: Synthesis of iV2-(c«-4-aminomethyl-cyC1-5hexyI)-5^V4^V4-trimethyl-pyrimidine-
2,4-diamine.
A mixture of 2-chloro-4-dimethyIamino-5-methylpyrimidine obtained in step A of example
3119 (3.00 g, 17.4 mmol) and (cw-4-amino-cyclohexyImethyl)-carbamic acid benzyl ester obtained in
step C of example 3068 (5.48 g, 20.9 mmol) in butanol (3 mL) was stirred at reflux for 70 hr. The
reaction mixture was poured into saturated aqueous NaHCO3 and the aqueous layer was extracted

680
with CHC13 {three times). The combined organic layer was dried over MgSO4, filtrated, concentrated,
and purified by flash chromatography (NH-silica, 33% to 50% EtOAc in hexane) to give a pale yellow
oil. To a solution of the above oil in MeOH (30 mL) was added 10% Pd/C (600 mg). The mixture
was stirred at ambient temperature under hydrogen atmosphere for 1.5 days. The reaction mixture was
filtrated through a pad of celite, concentrated, and purified by medium-pressure liquid
chromatography (NH-silica gel, 2% MeOH in CHC13) to give JV~-(ci.s-4-aminomethyl-cyclohexyl)-
5,A^,A^-trimethyl-pyrimidine-2,4-diamine (1.03 g, 22%) as a pale yellow solid.
ESI MS m/e 264, M (free) + H+ ; 'HNMR (300 MHz, CDC13) 5 1.15-1.89 (m, 11 H), 2.13 (s, 3 H),
2.59 (d, J= 6.4 Hz, 2 H), 3.02 (s, 6 H), 4.03-4.13 (m, 1 H), 4.77-4.85 (m, 1 H), 7.67 (s, 1 H).
Step B: Synthesis of l-(2,3-dichloro-phenyI)-3-[c/s-4-(4-dimethylamino-5-methyl-
py rim id in-2-ylamino)-cyC1-5hexyl methyl] -urea hydrochloride.
To a solution of A^-tcw^-aminomethyl-cyclohexyl^S^/Z-trimethyl-
pyrimidine-2,4-diamine (300 mg, 1.14 mmol) in DMSO (3 mL) was added
l,2-dichloro-3-isocyanato-benzene (236 mg, 1.25 mmol). The mixture was stirred at ambient
temperature for 16 hr and poured into water (20 mL). The precipitate was collected by filtration,
washed with water, and purified by medium-pressure liquid chromatography (NH-silica gel, 20%
EtOAc in hexane and silica gel, 3% MeOH in CHC13) to give a pale yellow oil. To a solution of the
above material in EtOAc (10 mL) was added 4 M hydrogen chloride in EtOAc (0.2 mL). The mixture
was stirred at ambient temperature for I hr and concentrated. A suspension of the residue in Et2O (20
mL) was stirred at ambient tempareture for I hr. The precipitate was collected by filtration, washed
with Et3O, and dried at 60 °C under reduced pressure to give l-(2,3-dich!oro-phenyl)-3-[c«-4-
(4-dimethylamino-5-methyI-pyrimidin-2-ylamino)-cyclohexylmethyl]-urea hydrochloride (326 mg,
59%) as a white solid.
ESI MS m/e 473, M (free) + Na+ ; *H NMR (200 MHz, CDC13) 5 1.45-1.99 (m, 9 H), 2.24 (s5 3 H),
3.30 (s, 6 H), 3.32-3.43 (m, 2 H), 4.22-4.38 (m, 2 H), 6.85-7.15 (m, 3 H), 7.22 (brs, 1 H), 8.14-8.26
(m, 2 H), 8.49-8.62 (m, 1 H), 12.14 (s, 1 H).

681
Example 3126
Ar-[c«-4-(4-Dimethylamino-6-methyl-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-
nicotinamide hydrochloride
Step A: Synthesis of (2-chloro-6-methyl-pyrimidin-4-yl)-dimethyl-amine.
To the solution of 2,4-dichloro-6-methylpyrimidine (20.0 g, 123 mmol) in THF (200 mL) was
added 50% aqueous Me?NH (13.3 g, 147 mmol) and the mixture was stirred at ambient temperature
for 24 hr. To the reaction was added saturated aqueous NaHCO3 and the aqueous layer was extracted
with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated,
and purified flash chromatography (NH-silica gel, 5% to 16% EtOAc in hexane) to give
(2-chloro-6-methyl-pyrimidin-4-yl)-dimethyI-amine (14.4 g, 68 %) as a pale yellow solid and
(4-chloro-6-methyl-pyrimidin-2-yI)-dimethyl-amine (6.57 g, 31%) as a pale yellow solid.
(2 -ch 1 oro-6-methy I-pyri m id in-4 -yl)-d imethy 1-am ine;
ESI MS m/e 194, M+ + Na+ ; lHNMR (300 MHz, CDC13) 5 2.34 (s, 3 H), 3.10 (s, 6 H), 6.16 (s, 1 H).
(4-chloro-6-methyl-pyrimidin-2-yl)-dimethyl-amine;
CI MS m/e 172, M + H+; lHNMR (300 MHz, CDC13) 5 2.29 (s, 3 H), 3.16 (s, 6 H), 6.34 (s, 1 H).
Step B: Synthesis of A^-[c«-4-(4-d imethy lam ino-6-methyl~py rim id in-2-y lam ino)-
cyclohexyl]-2-phenoxy~nicotinamide hydrochloride.
A mixture of (2-chloro-6-methyl-pyrimidm-4-yl) 7V-(ci.s-4-arnino-cyC1-5hexyl)-2-phenoxy-nicotinamide obtained in step A of example 3032 (598 mg,
1.92 mmol) in butanol (1 mL) was stirred at 130 °C for 40 hr in a sealed tube. The reaction mixture
was poured into saturated aqueous NaHCO3 and the aqueous layer was extracted with CHCI3 (three
times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica gel, 20% to 50% EtOAc in hexane). To a
solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL).
The mixture was stirred at ambient temperature for I hr and concentrated. The residue was

682
suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature for 2 hr. The
precipitate was filtered, washed with Et2O, and dried at 60 °C under reduced pressure to give
Ar-[ci5-4-(4-dimethylamino-6-methyI-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-nicotinamide
hydrochloride (549 mg, 65%) as a white solid.
ESI MS m/e 447, M(free) + H+;'HNMR (300 MHz, CDC13) 5 1.67-2.05 (m, 8 H), 2.34 (s, 3 H), 3.12
(s, 3 H), 3.23 (s, 3 H), 4.03-4.22 (m, 2 H), 5.71 (s, 1 H), 7.13 (dd, J= 7.5, 4.8 Hz, 1 H), 7.21-7.32 (m,
3 H), 7.41-7.51 (m, 2 H), 7.84-7.95 (m, 1 H), 8.21 (dd, J= 4.7, 2.1 Hz, 1 H), 8.45-8.57 (m, 2 H), 13.43
(brs, 1 H).
Example 3127
^'-^/^-^(^dimethylamino^-methyl-pyriniidin-l-ylaniinoJ-cyclohexyll-S^-difluoro-benzamid
e hydrochloride
Step A: Synthesis of Ar2-(ciy-4-amino-cyclohexyl)-6^v'^V'-trimethyl-pyrimidine-2,4-diamine.
A mixture of (2-chloro-6-methyl-pyrimidin-4-yl)-dimethyl-amine (6.00 g, 35.0 mmol) and
(c/5-4-amino-cyC1-5hexyl)-carbamic acid tert-buty\ ester obtained in step B of example 3031 (8.30 g,
38.5 mmol) in butanol (6 mL) was stirred at 130 °C for 48 hr. The reaction mixture was poured into
saturated aqueous NaHCO3 and the aqueous layer was extracted with CHCI3 (three times). The
combined organic layer was dried over MgSO4, filtered, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica gel, 16% to 50% EtOAc in hexane). To a
solution of the above material in EtOAc (60 mL) was added 4 M hydrogen chloride in EtOAc (60 mL).
The mixture was stirred at ambient temperature for 2 hr and concentrated. The residue was dissolved
in 1 M aqueous NaOH and the aqueous layer was extracted with CHC13 (three time). The combined
organic layer was dried over MgSO4, filtered, concentrated, and purified by medium-pressure liquid
chromatography (NH-silica gel, 2% to 10% MeOH in CHC13) to give
Af2-(cw-4-amino-cyclohexyl)-6/vr'/^-trimethyl-pyrimidine-2,4-diamine (2.29 g, 26%) as a pale
yellow oil.

683
ESIMSm/e25O,M + H+;1HNMR(3OOMHz,CDCl3)51.18-1.5O(m,4H), 1.58-1.93 (m, 6 H), 2.19
(s, 3 H), 2.76-2.87 (m, 1 H), 3.03 (s, 6 H), 3.96-4.06 (m, 1 H), 4.78-4.89 (m, 1 H), 5.67 (s, 1 H).
Step B: Synthesis of Ar-[C1-5-4-(4-dimethylamino-6-methyl-pyrimidini-2-ylamino)-cyC1-5hexyl]-
3,4-difluoro-benzamide hydrochloride
To a solution of A^-( mg, 1.20 mmol) in CHC13 (2 tnL) were added /-Pr2NEt (0.44 mL, 2.52 mmol) and
3,4-difluoro-benzoyl chloride (233 mg, 1.32 mmol) in CHCI3 (1 mL). The mixture was stirred at
ambient temperature for 15 hr. The reaction was quenched with saturated aqueous NaHCO3 and the
aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over
MgSO4, filtered, concentrated, and purified by medium-pressure liquid chromatography (NH-silica
gel, 20% EtOAc in hexane) to give a colorless oil. To a solution of the above material in EtOAc (10
mL) was added 4 M hydrogen chloride in EtOAc (0.2 mL). The mixture was stirred at ambient
temperature for 1 hr and concentrated. The residue was suspended in Et2O (20 mL) and the
suspension was stirred at ambient temperature for 2 hr. The precipitate was collected by filtration,
washed with Et^O, and dried at 60 °C under reduced pressure to give JV-[CZS-4-(4-
dimethylamino-6-methyl-pyrimidin-2-yIamino)-cyclohexyl]-3,4-difluoro-benzamide hydrochloride
(359 mg, 70%) as a white solid.
ESI MS m/e 390, M (free) + Vt; ]H NMR (300 MHz, CDC13) 5 1.64-2.00 (m, 8 H), 2.35 (d, J = 0.6
Hz, 3 H), 3.14 (s, 3 H), 3.26 (s, 3 H), 4.03-4.29 (m, 2 H), 5.74 (d, J= 0.7 Hz, 1 H), 6.61-6.72 (m, 1
H), 7.14-7.26 (m, 1 H), 7.53-7.62 (m, 1 H), 7.67-7.78 (m, 1 H), 8.59 (d, J= 7.8 Hz, 1 H).
Example 3128
3-Chloro-iV-[c/j-4-(4-dimethylaniino-6-inethyl-pyrimidin-2-ylamino)-cyclohexyl]-benzamide
hydrochloride
Step A: Synthesis of 3-chloro-iV-[c/y-4-(4-dimethylamino-6-methyl-pyriniidin-

684
2-ylamino)-cyclohexyl]-benzamide hydrochloride.
Using the procedure for the step B of example 3127, the title compound was obtained.
ESI MS m/e 410, M(free) + Na+ ; !HNMR (300 MHz, CDC13) 5 1.67-2.00 (m, 8 H), 2.35 (s, 3 H),
3.13 (s, 3 H), 3.25 (s, 3 H), 4.04-4.26 (m, 2 H), 5.75 (s, 1 H), 6.53 (d, 7 = 8.6 Hz, 1 H), 7.32-7.48 (m,
2 H), 7.64-7.70 (m, 1 H), 7.83 (t, 7= 1.9 Hz, 1 H), 8.60 (d, J= 7.9 Hz, 1 H), 13.11 (brs, 1 H).
Example 3129
A^c/s-4-(4-Dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-nicotinamide
hydrochloride
Step A: Synthesis of (2-chloro-py rim id in-4-yl)-di methyl-am in e.
To a solution of 2,4-dichloro-pyrimidine (15.0 g, 10.15 mmol) in THF (150 mL) was added
50% aqueous MeNH2 (22.7 g, 25.2 mmol). The mixture was stirred at ambient temperature for 2 hr.
The solution was poured into saturated aqueous NaHCC>3 and the aqueous layer was extracted with
CHC13 (three times). The combined organic layer was dried over MgSO4, filtrated, concentrated, and
purified by flash chromatography (NH-silica, 20% EtOAc in hexane) to give (2-chloro-
pyrimidin-4-yl)-dimethyl-amine (8.66 g, 55%) as a white solid and (4-chIoro-pyrimidin-2-yl)-
dimethyl-amine (0.87 g, 6%) as a white solid.
(2-chloro-pyrimidin-4-yl)-dimethyI-arnine;
CI MS m/e 158, M + it; 'HNMR (300 MHz, CDC13) 5 3.12 (s, 6 H), 6.32 (d, 7 = 6.1 Hz, 1 H), 8.00
(d, 7=6.1 Hz, 1 H).
(4-chloro-pyrimidin-2-yl)-dimethyI-amine;
ESI MS m/e 157, M+; !H NMR (300 MHz, CDC13) 5 3.21 (s, 6 H), 6.50 (d, 7= 5.1 Hz, 1 H), 8.18 (d,
7-5.1 Hz, 1 H).
Step B: Synthesis of [c/s-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-carbamic acid

685
ferf-butyl ester.
A mixture of (2-chIoro-pyrimidin-4-yI)-dimethyl-amine (1.50 g, 9.52 mmol) and
(c«-4-amino-cyclohexyI)-carbamic acid tert-buty\ ester obtained in step B of example 3031 (2.24 g,
10.5 mmol) in IPA (1.5 mL) was stirred at 130 °C for 22 hr in a sealed tube. The reaction mixture was
poured into saturated aqueous NaHCO3, and the aqueous layer was extracted with CHCI3 (three times).
The combined organic layer was dried over MgSO4, filtrated, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica, 10% EtOAc in hexane) to give [cis-4-(4-
dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-carbamic acid tert-buty] ester (1.34 g, 42%) as a
white solid.
ESI MS m/e 358, M + Na+ ; ]H NMR (300 MHz, CDC13) 5 1.45 (s, 9 H), 1.48 (s, 8 H), 3.03 (s, 6 H),
3.61 (brs, 1 H), 3.89-4.04 (m, 1 H), 4.47-4.63 (m, 1 H),4.77-4.89 (m, 1 H), 5.80 (d, 7=6.1 Hz, 1 H),
7.84 (d, 7= 6.1 Hz, I H).
Step C: Synthesis of ^-(cw-^amino-cyclohexylJ-A^A^dimethyl-pyrimidine^^-diamine.
To a solution of [c/5-4-(4-dimethy!amino-pyrimidin-2-ylamino)-cyclohexyI]-carbamic acid
tert-butyl ester (1.26 g, 3.76 mmol) in EtOAc (15 mL) was added 4 M hydrogen chloride in EtOAc
(15 mL). The reaction mixture was stirred at ambient temperature for 1 hr and concentrated. The
residue was alkalized with 1 M aqueous NaOH. The aqueous layer was extracted with CHC13 (six
times). The combined organic layer was dried over MgSC>4, filtrated, and concentrated to give
1 Ar2-(cij-4-amino-cyclohexyl)-Ar ^v -dimethyl-pyrimidine-2,4-diarnine (923 mg, quant.) as a pale
yellow oil.
ESI MS m/e 250, M + H+;]H NMR (300 MHz, CDC13)S 1.29-1.51 (m, 2 H), 1.61-1.91 (m, 6 H),
2.80-2.92 (m, 1 H), 3.03 (s, 6 H), 3.96-4.04 (m, 1 H), 4.85-4.98 (m, 1 H), 5.79 (d, J= 6.1 Hz, 1 H),
7.84 (d, J= 6.1 Hz, 1H).
Step D: Synthesis of Ar-[c/5-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-
nicotinamide hydrochloride.
To a solution of Ar2-(c/5-4-amino-cyclohexyl)-7V4^V4-dimethyl-pyrimidine-2,4-diamine (300

686
mg, 1.20 mmoJ) in CHC13 (3 mL) were added Et3N (0.35 mL, 2.51 mmol) and 2-phenoxy-nicotinoyl
chloride (309 mg, 1.32 mmol). The mixture was stirred at ambient temperature for 22 hr. The
reaction was quenched with saturated aqueous NaHCO3 and the aqueous layer was extracted with
CHCI3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated, and
purified by medium-pressure liquid chromatography (NH-silica gel, 20% to 50% EtOAc in hexane
and silica gel, 3% MeOH in CHCI3). To a solution of the above material in EtOAc (2 mL) was added
4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 1 hr
and concentrated. The residue was suspended in Et2O (20 mL) and the suspension was stirred at
ambient temperature for 2 hr. The precipitate was collected by filtration, washed with Et2O, and dried
at 80 °C under reduced pressure to give A^-[cw-4-(4-dimethylamino-pyrimidin-2-ylamino)-
cyC1-5hexyl]-2-phenoxy-nicotinamide hydrochloride (150 mg, 26%) as a white solid.
ESI MS m/e 433, M(free) + H+
Example 3130
S^-Difluoro-A^lc/y^-f^trifluoromethyl-pyriniidin-Z-yOamino-cyclohexyll-benzamide
hydrochloride
Step A: Synthesis of 3,4-difluor0-iV-[c/s-4-(4-trifluoromethyl-pyrimidin-2-yl)amino-
cyclohexyl]-benzamide hydrochloride.
A mixture of 2-chloro-4-trifluoromethyl-pyrimidine (200 mg, 1.09 mmol) and
jV-(c/5-4-amino-cyclohexyl)-3,4-difluoro-benzamide obtained in step D of example 3031 (306 mg,
1.20 mmol) in butanol (1 mL) was stirred at 130 °C for 12 hr in a sealed tube. The reaction mixture
was poured into saturated aqueous NaHCC>3 and the aqueous layer was extracted with CHC13 (three
times). The combined organic layer was dried over MgSO,), filtered, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica gel, 20% to 50% EtOAc in hexane). To a
solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL).
The mixture was stirred at ambient temperature for 1 hr and concentrated. The residue was

687
suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature for 2 hr. The
precipitate was collected by filtration, washed with Et?O, and dried at 80 °C under reduced pressure to
give3,4-difluoro-7VL[cw-4-(4-trifluoromethyl-pyrimidin-2~yI)amino-cyclohexyi]-benzamide
hydrochloride (123 mg, 26%) as a white solid.
ESI MS m/e 423, M+ (free) + Na+
Example 3131
3,4-Difluoro-A'-[c/s-4-(4-methoxy-pyrimidin-2-ylamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 3,4-difluoro-Ar-[cK-4-(4-methoxy-pyrimidin-2-ylamino)-cyclohexyl]-
benzamide hydrochloride.
Using the procedure for the step A of example 3130, the title compound was obtained.
ESI MS m/e 385, M (free) + Na+
Example 3132
7V-[c«-4-(4,6-Dimethoxy-pyrimidin-2-ylamino)-cyclohexyl]-3,4-difluoro-benzaniide
hydrochloride
Step A: Synthesis of 7V-[cw-4-(4,6-dimethoxy-pyrimidin-2-ylamino)-cyC1-5hexyl]-3,4-difluoro-
benzamide hydrochloride.
Using the procedure for the step A of example 3130, the title compound was obtained.
ESI MS m/e 415, M (free)+ Na+
Example 3133
Z-Phenoxy-A^Icw^^-trifluoromethyl-pyrimidin^-yO-amino-cyclohexyll-nicotinamide

688
hydrochloride
Step A: Synthesis of 2-phenoxywV-[as-4-(4-trifluoromethyl-pyrimidin-2-yl)-amino-cyclohexyl]-
nicotinamide hydrochloride.
A mixture of 2-chloro-4-trifluoromethyl-pyrimidine (200 mg, 1.10 mmol) and
7V-(cw-4-amino-cyclohexyl)-2-phenoxy-nicotinamide obtained in step A of example 3032 (375 mg,
1.20 mmol) in butanol (1 mL) was stirred at 130 °C for 3 days in a sealed tube. The reaction mixture
was poured into saturated aqueous NaHCO3 and the aqueous layer was extracted with CHCI3 (three
times). The combined organic layer was dried over MgSCU, filtered, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica gel, 20% to 33% EtOAc in hexane) to give a pale
yellow oil. To a solution of the above material in EtOAc (10 mL) was added 4 M hydrogen chloride
in EtOAc (0.2 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated. The
residue was suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature for 2
hr. The precipitate was collected by filtration, washed with Et2O, and dried at 60 °C under reduced
pressure to give 2-phenoxy-N-[c/5-4-(4-trifiuoromethyl-pyrimidin-2-yl)-amino-cyclohexyl]-
nicotinamide hydrochloride (111 mg, 21%) as a white solid.
ESI MS m/e 480, M (free) + Na+
Example 3134
Ar-[cis-4-(4-Methoxy-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-nicotinaniide
hydrochloride
Step A: Synthesis of Ar-[c/s-4-{4-methoxy-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-
nicotinamide hydrochloride.
Using the procedure for the step A of example 3133, the title compound was obtained.
ESI MS m/e 442, M (free) + Na+

689
Example 3135
Ar-[a5-4-(4,6-Dimethoxy-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-nicotinaniide
hydrochloride
Step A: Synthesis of 7V-[ctf-4-(4,6-dimethoxy-pyrimidin-2-ylamino)-cyclohexylJ-2-phenoxy-
nicotinamide hydrochloride.
Using the procedure for the step A of example 3133, the title compound was obtained.
ESI MS m/e 472, M (free) + Na+
Example 3136
Ar-[c/5-4-(4-Dimethylamino-5-phenyl-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-
nicotinamide hydrochloride
Step A: Synthesis of (5-bromo-2-chloro-pyrimidin-4-yl)-dimethyl-amine.
Using the procedure for the step A of example 3129, the title compound was obtained.
ESIMSm/e236,M + H+
Step B: Synthesis of (2-chloro-5-phenyl-pyrimidin-4-yl)-dimethyl-amine.
To a solution of (5-bromo-2-chIoro-pyrimidin-4-yl)-dimethyl-amine (2.00 g, 8.46 mmol) in
toluene (30 mL) were added 2 M aqueous K2CO3 (15 mL), phenylboronic acid (1.03 g, 8.45mmol),
and tetrakis-(triphenylphosphine)-palladium (977 mg, 0.845 mmol). The reaction mixture was stirred
at reflux for 8 hr. The mixture was poured into water and the aqueous layer was extracted with CHC13
(three times). The combined organic layer was dried over MgSO,*, filtered, concentrated, and purified
by flash chromatography (NH-silica gel, 3% EtOAc in hexane) to give (2-chloro-5-phenyl-pyrimidin-
4-yl)-dimethyl-amine (1.44 g, 73%).
ESIMSm/e256,M+Na+

690
Step C: Synthesis of AL[c/y-4-(4-dimethylamino-5-phenyl-pyrimidin-2-ylamino)-cyclohexyl]-
2-phenoxy-nicotinamide hydrochloride.
Using the procedure for the step A of example 3133, the title compound was obtained.
ESI MS m/e 531, M (free) + Na+
Example 3137
Ar-[cw-4-(5-Chloro-4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-
nicotinamide hydrochloride
Step A: Synthesis of (2,5-dichloro-pyrimidin-4-yl)-dimethyl-amine.
Using the procedure for the step A of example 3129, the title compound was obtained.
ESI MS m/e 191, M+
Step B: Synthesis of Af-[c/s-4-(5-chloro-4-dimethylamino-pyrimidin-2-ylamino)-cyC1-5hexyl]-
2-phenoxy-nicotinamide hydrochloride.
Using the procedure for the step A of example 3133, the title compound was obtained.
ESI MS m/e 467, M (free) + H+
Example 3138
iV-[c/s-4-(4-Dimethylamino-5-phenyI-pyrimidin-2-ylamino)-cyclohexyl]-3,4-difluoro-
benzamide hydrochloride
Step A: Synthesis of Ar-[c/$-4-(4-dimethylamino-5-phenyl-pyrimidin-2-ylamino)-cyclohexyl]-
3,4-difluoro-benzamide hydrochloride.
Using the procedure for the step A of example 3130, the title compound was obtained.
ESI MS m/e 474, M (free) + Na+

691
Example 3139
iV-[m-4-(5-Chloro-4-dimethylamino-pyrimidin"2-ylamino)-cyclohexyl]-3,4-difluoro-
benzamide hydrochloride
Step A: Synthesis of 7V-[c/y-4-(5-chloro-4-dimethyIamino-pyrimidin-2-ylamino)-cyclohexyl]-
3,4-difiuoro-benzamide hydrochloride.
Using the procedure for the step A of example 3130, the title compound was obtained.
ESI MS m/e 432, M(free) + Na+
Example 3140
Ar-[c/5-4-(4-DimethyIamino-5-fluoro-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-
nicotinamide hydrochloride
Step A: Synthesis of (2-chloro-5-fluoro-pyrimidin-4-yl)-dimethyl-amine.
Using the procedure for the step A of example 3129, the title compound was obtained.
ESIMSm/el76,M + H+
Step B: Synthesis of iV-[c/5-4-(4-dimethylamino-5-fluoro-pyrimidin-2-yIamino)-cyclohexyl]-2-
phenoxy-nicotinamide hydrochloride.
Using the procedure for the step A of example 3133, the title compound was obtained.
ESI MS m/e 451, M (free) + H+
Example 3141
7V-[cw-4-(5-Bromo-4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-
nicotinamide hydrochloride

692
Step A: Synthesis of AL[m-4-(5-bromo-4~dimethylamino-pyrimidiii-2-ylamino)-cyclohexyl]-
2-phenoxy-nicotinamide hydrochloride.
Using the procedure for the step A of example 3133, the title compound was obtained.
ESI MS m/e 533, M (free) + Na+
Example 3142
7V-[m-4-(4,6-Dimethyl-pyrimidin-2-ylamino)-cyclohexyl]-3,4-difluoro-benzamide
hydrochloride
Step A: Synthesis of Ar-[a5-4-(4,6-dimethyl-pyrimidin-2-yIamino)-cyclohexyl]-3,4-difluoro-
benzamide hydrochloride.
Using the procedure for the step A of example 3130, the title compound was obtained.
ESI MS m/e 383, M (free) + Na+
Example 3143
7V-[m-4-(4,6-Dimethyl-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-iiicotinamide
hydrochloride
Step A: Synthesis of Ar-[c«-4-(4T6-dimethyl-pyrimidin-2-ylamino)-cyclohexyl]-2-phenoxy-
nicotinamide hydrochloride.
Using the procedure for the step A of example 3133, the title compound was obtained.
ESI MS m/e 440, M (free) + Na+
Example 3144
3,4-Difluoro-iV-[c/s-4-(pyrimidin-2-ylamino)-cyclohexyl]-benzamide hydrochloride

693
Step A: Synthesis of 3,4-difluoro-iV-{cw-4-(pyrimidin-2-ylamino)-cyclohexyI]-benzamide
hydrochloride.
Using the procedure for the step A of example 3130, the title compound was obtained.
ESI MS m/e 355, M(free) + Na+
Example 3145
Ar-[C1-5-4-(4-Dimethylamino-pyrimidin-2-ylainino)-cyclohexylmethyl]-2-phenoxy-nicotinamide
hydrochloride
Step A: Synthesis of [cjs-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexylmethyl]-
carbamic acid benzyl ester.
A mixture of (2-chIoro-pyrimidin-4-yI)-dimethyl-arnine obtained in step A of example 3129
(1.50 g, 9.52 mmol) and (c/5-4-amino-cyclohexylmethyl)-carbamic acid benzyl ester obtained in step
C of example 3068 (2.75 g, 10.5 mmol) in IPA (1.5 mL) was stirred at 130 °C for 22 hr in a sealed tube.
The reaction mixture was poured into saturated aqueous NaHCC>3 and the aqueous layer was
extracted with CHC13 (three times). The combined organic layer was dried over MgSO4, filtrated,
concentrated, and purified by medium-pressure liquid chromatography (NH-silica, 10% EtOAc in
hexane to EtOAc) to give [c^-4-(4-dimethyIamino-pyrimidin-2-ylamino)-cyclohexylmethyl]-
carbamic acid benzyl ester (816 mg, 22%) as a pale yellow oil.
ESI MS m/e 406, M + Na+;!HNMR (300 MHz, CDCI3) 6 1.22-1.92 (m, 9 H), 3.03 (s, 6 H), 3.11 (t,
J= 6.2 Hz, 2 H), 4.02-4.15 (m, 1 H), 4.82-4.93 (m, 2 H), 5.10 (s, 2 H), 5.79 (d, J= 6.1 Hz, 1 H),
7.28-7.42 (m, 5 H), 7.83 (d, J= 6.1 Hz, 1 H).
Step B: Synthesis of 7V2-(cis-4-aminomethyl-cyC1-5hexyl)-A'4,A' -dimethyl-pyrimidine-
2,4-diamine.
Using the procedure for the step B of example 3118, the title compound was obtained.

694
ESI MS m/e 250, M + H+ ; 'H NMR {300 MHz, CDCI3) 5 1.40-1.88 (m, 9 H), 2.87 (d, J = 5.9 Hz, 2
H), 3.03 (s, 6 H), 4.11 (brs, 1 H), 5.63 (brs, I H), 5.78 (d, J= 6.2 Hz, 1 H), 7.08 (brs, 2 H), 7.82 (d,
J-6.2 Hz, 1 H).
Step C: Synthesis of A^crM-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexylinethyl]-2-
phenoxy-nicotinamide hydrochloride.
To a solution of N -(cw-4-aminomethyI-cyclohexyl)-7V47/v -dimethyI-pyrimidine-2,4-
diamine (400 mg, 1.60 mmol) in CHC13 (2 mL) were added i-Pr2NEt (0.56 mL, 3.36 mmol) and
2-phenoxy-nicotinoyl chloride (523 mg, 2.24 mmol) in CHCI3 (2 mL). The mixture was stirred at
ambient temperature for 5 hr. The reaction was quenched with saturated aqueous NaHCO3 and the
aqueous layer was extracted with CHCI3 (three times). The combined organic layer was dried over
MgSO4, filtered, concentrated, and purified by medium-pressure liquid chromatography (NH-silica
gel, 20% to 50% EtOAc in hexane) to give a colorless oil. To a solution of the above material in
EtOAc (10 mL) was added 4 M hydrogen chloride in EtOAc (0.2 mL). The mixture was stirred at
ambient temperature for 1 hr and concentrated. The residue was suspended in Et2O (20 mL) and the
suspension was stirred at ambient temperature for 2 hr. The precipitate was collected by filtration,
washed with Et2O, and dried at 60 °C under reduced pressure to give 7V-[c/s-4-(4-dimethylamino-
pyrimidin-2-ylamino)-cyclohexylmethyl]-2-phenoxy-nicotinamide hydrochloride (199 mg, 26%) as a
white solid.
ESI MS m/e 469, M (free) + Na+
Example 3146
3-Hydroxy-Af-[cw-4-(quinolin-2-yIamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 3-hydroxy-A'-[c/5-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide
hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.

695
ESI MS m/e 362, M (free) + H+; 'H NMR (300 MHz, DMSO-d6) 5 1.60-2.09 (m, 8 H), 3.83-4.02 (m,
1 H), 4.22-4.49 (m, 1 H), 6.79-7.02 (m, 1 H), 7.12-7.59 (m, 5 H), 7.67-8.45 (m, 5 H), 9.40-9.78 (m,
2H), 12.91-13.17 (m, I H).
Example 3147
A^cw-4-(Quinolin-2-ylamino)-cyclohexyl]-isophthalamic acid methyl ester hydrochloride
Step A: Synthesis of Ar-[cw-4-(quinolin-2-ylamino)-cyclohexyI]-isophthaIamic acid methyl ester
hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 404, M (free) + H+; 'H NMR (300 MHz, CDC13) 5 1.54-2.12 (m, 8 H), 3.89-4.31 (m, 5
H), 6.89-7.05 (m, 2 H), 7.41-7.58 (m, 2 H), 7.68-7.82 (m, 3 H), 8.00-8.22 (m, 3 H), 8.46-8.51 (m, 1
H), 9.66-9.85 (m, I H).
Example 3148
Ar-[cw-4-(QuinoIin-2-ylamino)-cyclohexyll-3,5-bis-trifluoromethyl-
benzamide hydrochloride
i
Step A: Synthesis of 7V-[c/$-4-(quinolin-2-ylamino)-cyclohexyl]-3,5-bis-trifluoromethyI-
benzamide hydrochloride.
Using the procedure for the step A of example 3046, the title compound was obtained.
ESI MS m/e 482, M (free) + H+; *H NMR (300 MHz, CDC13) 8 1.75-2.27 (m, 8 H), 4.00-4.32 (m, 2
H), 6.97 (d, J = 9.4 Hz, 1 H), 7.42-7.65 (m, 2 H), 7.69-7.80 (m, 3 H), 7.96-8.02 (m, 1 H), 8.20 (d, J
= 9.3 Hz, 1 H), 8.35-8.42 (m, 2 H), 9.69-9.79 (m, 1 H).

696
Example 3149
Ar-[c/y-4-(QuinoIin-2-ylamino)-cyclohexyl]-3-trifluoromethoxy-benzamide hydrochloride
Step A: Synthesis of Ar-[c«-4-(Quinolin-2-ylamino)-cyclohexyl]-3-trifluoromethoxy-
benzamide hydrochloride.
Using the procedure for the step A of example 3046, the title compound was obtained.
ESI MS m/e 430, M (free) + H+; 'H NMR (300 MHz, CDCI3) 6 1.77-2.33 (m, 8 H), 3.96-4.29 (m, 2
H), 6.88-7.03 (m, 2 H), 7.29-7.51 (m, 3 H), 7.69-7.82 (m, 5 H), 8.19 (d, J = 9.5 Hz, 1 H), 9.73-9.86
(m, 1 H).
Example 3150
A-|t7v-4-(Quinolin-2 yluniino)-cvil(ihexyl|-isophlhalamic acid
Step A: Synthesis of iV-[cw-4-(quiDoIin-2-ylamino)-cyclohexyl]-isophthalamic acid methyl
ester.
To a solution of isophthalic acid monomethyl ester (435 mg) and cw-/V-quinolin-2-yl-
cyclohexane-l,4-diamine obtained in step A of example 3033 (500 mg) in DMF (5 mL) were added
Et3N (0.96 mL), HOBt-H2O (476 mg), and EDC-HC1 (437 mg). The reaction mixture was stirred at
ambient temperature for 18 hr. To the reaction mixture was added water (20 mL) and the suspension
was stirred at ambient temperature for 30 min. The precipitated was collected by filtration, washed
with H?O, and purified by medium-pressure liquid chromatography (NH-silica gel, 25% EtOAc in
hexane) to give A4cw-4-(quinolin-2-ylamino)-cyC1-5hexyl]-isophthalamic acid methyl ester (740 mg)
as a white solid.
ESI MS m/e 404, M + H+; 'H NMR (300 MHz, CDC13) 6 1.71-2.05 (m, 8 H), 3.96 (s, 3 H), 4.10-4.28
(m, 2 H), 4.80-4.90 (m, 1 H), 6.16-6.26 (m, 1 H), 6.66 (d, J= 8.8 Hz, 1 H), 7.18-7.20 (m, 1 H),
7.49-7.68 (m, 4 H), 7.84 (d, J- 8.3 Hz, 1 H), 8.03-8.10 (m, 1 H), 8.15-8.22 (m, 1 H), 8.35-8.38 (m,
1H).

697
Step B: Synthesis of iV-[c/s-4-(QuinoHn-2-ylamino)-cyC1-5hexyl]-isophthalainic acid.
To a solution of Ar-[c«-4-(quinolin-2-yIamino)-cyclohexyI3-isophthalamic
acid methyl ester (400 mg) inEtOH(12 mL) was added 2 M aqueous NaOH (0.52 mL). The reaction
mixture was stirred at ambient temperature for 11 hr. To the reaction mixture was added 1 M aqueous
HC1 (0.6 mL) and the aqueous layer was extracted with CHC13 (three times). The combined organic
layer was dried over MgSO4, filtered, concentrated under reduced pressure, purified by medium-
pressure liquid chromatography (silica gel, 1 % to 5% MeOH in CHCI3) to give a white solid. The
suspension of above solid in Et2O (20 mL) was stirred at ambient temperature for 1 hr and filtered to
to give 7V-[c/5-4-(Quinolin-2-ylamino)-cyclohexyI]-isophthalamic acid (183 mg) as a white solid.
ESI MS m/e 412, M (free) + Na+;'HNMR (300 MHz, DMSO-d6) 5 1.63-2.09 (m, 8 H), 3.84-4.18 (m,
2 H), 6.83-6.91 (m, 2 H), 7.07-7.17 (m, 1 H), 7.39-7.64 (m, 4 H), 7.83 (d,J = 9.0 Hz, 1 H), 8.03-8.13
(m, 2 H), 8.39-8.53 (m, 2 H).
Example 3151
C-(Ethyl-phenyl-amino)-Ar-[cw-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide dihydrochloride
Step A: Synthesis of C-(ethyl-phenyl-amino)-iV-[c«-4-(quinolin-2-yIamino)-cyC1-5hexyl]-
acetamide dihydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 403, M (free) + if; 'HNMR (300 MHz, CDC13) 5 1.18-1.36 (m, 3 H), 1.54-2.15 (m, 8
H), 3.39-3.65 (m, 3 H), 3.68-4.11 (m, 3 H), 6.80-7.20 (m, 3 H), 7.29-7.86 (m, 8 H), 8.07-8.23 (m, 1
H), 9.48-9.68 (m, 1 H).
Example 3152
3,5-Difluoro-AL[c/s-4-(quinolin-2-ylainino)-cyclohexyl]-benzamide hydrochloride

698
Step A: Synthesis of 3,5-Difluoro-iV-[ro-4-(qiiinoliii-2-yIamino)-cyclohexyl]-
benzamide hydrochloride.
Using the procedure for the step A of example 3046, the title compound was obtained.
ESI MS m/e 404, M (free) + Na*; !HNMR (300 MHz, DMSO-d6) 5 1.71-2.02 (m, 8 H), 3.87-4.13 (m,
I H), 4.24-4.53 (m, 1 H), 7.21-8.01 (m, 7 H), 8.18-8.60 (m, 3 H), 9.48-9.81 (m, 1 H), 13.09-13.28 (m,
1H).
Example 3153
4-ChIoro-3-fluoro-iV-[c/s-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide- hydrochloride
Step A: Synthesis of 4-chloro-3-fluoro-Ar-[cw-4-(quinolin-2-ylamino)-cyclohexyl]-
benzamide hydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 398, M (free) + H+; 'H NMR (300 MHz, CDC13) 8 1.80-2.10 (m, 8 H), 3.97-4.27 (m, 2
H), 6.88-7.03 (m, 2 H), 7.39-7.50 (m, 2 H), 7.54-7.62 (m, 1 H), 7.66-7.83 (m, 4 H), 8.19 (d, J= 9.4
Hz, 1 H), 9.65-9.82 (m, 1 H).
Example 3154
C-[(4-Chloro-phenyl)-ethyl-amino]-7V-|c/y-4-(quinolin-2-ylamino)-cyclohexyl]-
acetamide dihydrochloride
Step A: Synthesis of C-[(4-chloro-pheny1)-ethyl-amino]-Ar-[d5-4-(quinolin-
2~ylamino)-cyclohexyl]-acetamide dihydrochloride.
Using the procedure for the step A of example 3036, the title compound was obtained.
ESI MS m/e 459, M (free)+ Na+;lHNMR (300 MHz, DMSO-d6) 5 0.99-1.19 (m, 3 H), 1.42-1.96 (m,

699
8 H), 3.30-3.55 (m, 2 H), 3.71-3.87 (m, 1 H), 3.94 (s, 2 H), 4.29-4.51 (m, 1 H), 6.57-6.77 (m, 2 H),
7.02-7.58 (m, 4 H), 7.65-8.04 (m, 3 H), 8.15-8.44 (m, 2 H), 9.61-9.85 (m, 1 H), 13.17-13.42 (m, 1 H).
Example 3155
A-[(7v-4-(Quinolin-2 ylan]ino)-cyilohe\yl|-isophthulami(le hydrochloride
Step A: Synthesis of ./V-[c«-4-(quinolin-2-ylamino)-cyclohexyl]-
isophthalamide hydrochloride.
To a solution of Ar-[c/5-4-(quinolin-2-ylamino)-cyclohexyl]-isophthaIamic acid obtained in
step B of example 3150 (160 mg) in DMF (2 mL) were added 28% aqueous NH3 (30 mg), Et3N (0.14
mL), HOBt-H2O (94 mg), and EDC-HC1 (95 mg). The reaction mixture was stirred at ambient
temperature for 16 hr. To the reaction mixture was added water (20 mL) and the aqueous layer
extracted with CHC13 (three times). The combined organic layer was dried over MgSO4, filtered,
concentrated under reduced pressure, purified by medium-pressure liquid chromatography (NH-silica
gel, 20% to 50% EtOAc in hexane). The solution of above purified material in EtOH (3 mL) was
added 4 M hydrogen chloride in EtOAc (0.3 mL). The mixture was stirred at ambient temperature for
2 hr, filtered, and dried under reduced pressure to give Ar-[c/5-4-(quinolin-2-yIamino)-cyclohexyl]-
isophthalamide hydrochloride (9 mg) as a white solid.
ESI MS m/e 411, M (free) + Na+; 'HNMR (300 MHz, DMSO-d6) 5 1.70-2.06 (m, 8 H), 3.89-4.08 (m,
1 H), 4.19-4.39 (m, 1 H), 7.17-7.60 (m, 4 H), 7.71-8.46 (m, 8 H), 12.84-12.97 (m, 1 H).
Example 3156
3,4-Difluoro-Ar-{a5-4-[(quinolin-2-ylmethyl)-amino]-cyclohexylJ-
benzamide dihydrochloride
Step A: Synthesis of 3,4-difluoro-iV-{c«-4-[(quinolin-2-ylmethyl)~amino]-

700
cyclohexylj-benzamidedihydrochloride.
To a solution of AMp.s-4-arnino-cyclohexyl)-3,4-difluoro-benzamide obtained in step D of
example 3031 (250 mg) in CHC13{5 mL) were added quinoIine-2-carbaldehyde (185 mg), acetic acid
(71 mg), and NaBH(OAc)3 (316 mg). The reaction mixture was stirred at ambient temperature for 16
hr. The reaction was quenched with saturated aqueous NaHCO3 and the aqueous layer was extracted
with CHCh (three times). The combined organic layer was dried over MgSO4, filtrated, concentrated
under reduced pressure, and purified by medium-pressure liquid chromatography (NH-silica gel, 20%
EtOAc in hexane and silica gel, 2% to 5% MeOH in CHC13) to give a colorless oil. To a solution of
the above oil in EtOAc (10 mL) was added 4 M hydrogen chloride in EtOAc (0.2 mL). The mixture
was stirred at ambient temperature for 1 hr and concentrated under reduced pressure. A suspension
of the above material in Et2O (12 mL) was stirred at ambient tempareture for 1 hr. The precipitate was
collected by filtration, washed with Et3O, and dried under reduced pressure to give 3,4-difluoro-jV-
{cw-4-[(quinolin-2-ylmethyI)-amino]-cyclohexyl}-benzamide dihydrochloride (100 mg) as a white
solid.
ESI MS m/e 418, M (free) + Na+; !H NMR (300 MHz, DMSO-d6) 6 1.50-1.68 (m, 2 H), 1.90-2.15 (m,
6 H), 3.20-3.37 (m, 1 H), 3.9M.01 (m, 1 H), 4.53-4.66 (m, 2 H), 7.46-8.29 (m, 9 H), 8.52 (d, J= 8.5
Hz, 1H), 9.44-9.62 (m, 2 H).
Example 3157
^-[ci^^-Methyl-quinolin^-ylamino^cyclohexylJ-SjS-bis-trifluoromethyl-benzamide
hydrochloride
Step A: Synthesis of A-[c/s-4-(4-methyl-quinolin-2-ylaniino)-cyclohexyl]-3,5-bis-
trifiuoromethyl-benzaniide hydrochloride.
Using the procedure for the step B of example 3070, the title compound was obtained.
ESI MS m/e 496, M (free) + H+; *H NMR (300 MHz, CDC13) 5 1.77-2.19 (m, 8 H), 2.74 (s, 3 H),
3.98-4.31 (m, 2 H), 6.78-6.81 (m, 1 H), 7.40-7.52 (m, 1 H), 7.58-7.78 (m, 3 H), 7.85 (d, J= 9.2 Hz,

701
1 H), 7.96-8.01 (m, 1 H), 8.36-8.41 (m, 2 H), 9.49-9.64 (m, 1 H).
Example 3158
7V-[m-4-(4-Methyl-quinolin-2-yIamino)-cyC1-5hexyl]-3-trifluoromethoxy-
benzamide hydrochloride
Step A: Synthesis of Ar-[cw-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyl]-3-
trifluoromethoxy-benzamide hydrochloride.
Using the procedure for the step B of example 3070, the title compound was obtained.
ESI MS m/e 444, M (free) + H+; 'H NMR (300 MHz, CDC13) 8 1.68-2.20 (m, 8 H), 2.71-2.75 (m, 3
H), 3.96-4.30 (m, 2 H), 6.76-6.87 (m, 2 H), 7.30-7.39 (m, 1 H), 7.42-7.52 (m, 2 H), 7.67-7.89 (m, 5
H), 9.50-9.72 (m, 1 H).
Example 3159
C-(Ethyl-phenyl-amino)-A^-[C1-5-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyl]-acetamide
dihydrochloride
Step A: Synthesis of C-(ethyI-phenyl-amino)-AL[m-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-acetamide dihydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 417, M (free) + H+; 'H NMR (300 MHz, CDC13) 5 1.10-1.38 (m, 3 H), 1.59-2.05 (m, 8
H), 2.45-2.84 (m, 3 H), 3.35-4.15 (m, 6 H), 6.57-6.81 (m, 1 H), 6.85-7.52 (m, 7 H), 7.57-7.89 (m, 4
H), 9.20-9.50 (m, 1 H).
Example 3160

702
3-Hydroxy-Ar-[C1-5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 3-hydroxy-AL[cw-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-
benzamide hydrochloride.
' ESI MS m/e 398, M (free) + Na+; *H NMR (300 MHz, DMSO-d6) 5 1.67-2.02 (m, 8 H), 2.53-2.70 (m,
3 H), 3.86-3.99 (m, 1 H), 4.24-4.40 (m, 1 H), 6.88-6.96 (m, 1 H), 7.06-7.31 (m, 4 H), 7.46-7.57 (m,
1 H), 7.73-7.83 (m, 1 H), 7.92-8.28 (m, 3 H), 9.66 (s, 1 H), 12.83-12.94 (m, 1 H).
I
Example 3161
2-Amino-iV-[c/s-4-(4-methyl-quinolin-2-ylamino)-cyclohexyll-nicotinamide dihydrochloride
Step A: Synthesis of 2-amino-7V-[ci5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
' nicotinamide dihydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 376, M (free) + H+; lHNMR (300 MHz, DMSO-d6) 8 1.63-2.06 (m, 8 H), 2.53-2.70 (m,
3 H), 3.87-4.04 (m, 1 H)5 4.36-4.59 (m, 1 H), 6.92-7.06 (m, 1 H), 7.15-7.27 (m, 1 H), 7.45-7.58 (m,
1 H), 7.69-7.84 (m, 1 H), 7.89-8.01 (m, 1 H), 8.14-8.58 (m, 4 H), 8.69-8.86 (m, 1 H), 9.54-9.72 (m,
I 1 H).
Example 3162
2,3-Difluoro-7V-[a5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-benzamide hydrochloride
Step A: Synthesis of 2r3-difluoro-iV-[c/s-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-benzamide hydrochloride.
Using the procedure for the step B of example 3070, the title compound was obtained.

703
ESI MS m/e 418, M (free) +Na+; *H NMR (300 MHz, CDCI3) 5 1.56-2.17 (m, 8 H), 2.72 (s, 3 H),
3.88-4.04 (m, 1 H), 4.09-4.30 (m, 1 H), 6.67-6.92 (m, 2 H), 7.10-7.35 (m, 2 H), 7.41-7.52 (m5 1 H),
7.60-7.93 (m, 4 H), 9.53-9.75 (m, 1 H).
Example 3163
2,4-Difluoro-JV-[m-4-(4-methyI-quinolin-2-yIamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 2,4-difluoro-Ar-[cis-4-(4-methyl-quinoIin-2-ylamino)-
cyclohexylj-benzamide hydrochloride.
Using the procedure for the step B of example 3070, the title compound was obtained.
ESI MS m/e 418, M (free) + Na+; *H NMR (300 MHz, CDC13) 5 1.57-2.22 (m? 8 H), 2.73 (s, 3 H),
3.87-4.06 (m, 1 H), 4.11-4.31 (m, 1 H), 6.69-7.06 (m, 4 H), 7.40-7.56 (m, 1 H), 7.65-7.88 (m, 3 H),
7.98-8.14 (m, 1 H), 9.51-9.83 (m, 1 H).
Example 3164
2,5-Difluoro-Ar-[c«-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 2,5-difluoro-7V-[c/5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
benzamide hydrochloride.
Using the procedure for the step B of example 3070, the title compound was obtained.
ESI MS m/e 418, M (free) + Na+; !HNMR (300 MHz, CDC13) 8 1.46-2.14 (m, 8 H), 2.72 (s, 3 H),
3.84-4.04 (m, 1 H), 4.09-4.32 (m, 1 H), 6.77 (s, 1 H), 6.82-7.21 (m, 3 H), 7.37-7.54 (m, 1 H),
7.63-7.89 (m, 4 H), 9.54-9.72 (m, 1 H).
Example 3165

704
2,6-Difluoro-Ar-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 2,6-dif]uoro-iV-[cis-4-(4-methyl-quinolin-2-ylamino)-
cyclohexylj-benzamide hydrochloride.
Using the procedure for the step B of example 3070, the title compound was obtained.
ESI MS m/e 418, M (free) + Na+; !H NMR (300 MHz, CDC13) 8 1.72-2.08 (m, 8 H), 2.72 (s, 3 H),
3.91-4.03 (m, 1 H), 4.13-4.33 (m, 1 H), 6.42-6.54 (m, 1 H), 6.77 (s, 1 H), 6.88-6.99 (m, 2 H),
7.27-7.50 (m, 2 H)5 7.66-7.78 (m5 2 H), 7.84 (d, J= 8.2 Hz, 1 H), 9.53-9.70 (m, 1 H).
Example 3166
3,5-Difluoro-Ar-[c«-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 3,5-difluoro-jV-[cis-4-(4-methyI-quinolin-2-ylamino)-
cyclohexylj-benzamide hydrochloride.
Using the procedure for the step B of example 3 070, the title compound was obtained.
ESI MS m/e 418, M (free) + Na+; 'H NMR (300 MHz, CDC13) 5 1.78-2.16 (m, 8 H), 2.72 (s, 3 H),
3.96-4.26 (m, 2 H), 6.78 (s, 1 H), 6.86-7.02 (m, 2 H), 7.33-7.52 (m, 3 H), 7.67-7.78 (m, 2 H), 7.85 (d,
J= 8.2 Hz, 1 H), 9.48-9.71 (m, 1 H).
Example 3167
C-[(4-Chloro-phenyl)-ethyl-amino]-jV-[c/s-4-(4-methyl-quinolin-2-yIamino)-
cyclohexylj-acetamide dihydrochloride
Step A: Synthesis of C-[(4-chloro-phenyl)-ethyl-amino]-Ar-Ic«-4-(4-methyl-quinolin-
2-ylamino)-cyclohexyl]-acetamide dihydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.

705
ESI MS m/e 451, M (free) + H+; 'HNMR (300 MHz, CDCh) 5 1.14-1.26 (m, 3 H), 1.69-2.00 (m, 8
H), 2.60 (s, 3 H), 3.39-3.61 (m, 2 H), 3.75-4.03 (m, 4 H), 6.63-7.06 (m, 4 H), 7.14-7.32 (m, 2 H),
7.39-7.51 (m, 1 H), 7.64-7.89 (m, 3 H), 9.44-9.59 (m, 1 H).
Example 3168
4-Chloro-3-fluoro-Ar-[C1-5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
benzamide hydrochloride
Step A: Synthesis of 4-chIoro-3-fluoro-7V-[cw-4-(4-methyl-quinolin-2-ylamino)-
cyclohexylj-benzamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 412, M (free) + rT; 'HNMR (300 MHz, CDC13) 6 1.78-2.13 (m, 8 H), 2.70-2.76 (m, 3
H), 3.95-4.28 (m, 2 H), 6.65-6.81 (m, 2 H), 7.41-7.50 (m, 2 H), 7.53-7.59 (m, 1 H), 7.65-7.77 (m, 3
H), 7.82-7.88 (m, 1 H), 9.57-9.71 (m, 1 H).
Example 3169
4-Fluoro-Ar-[c/$-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-benzamide hydrochloride
Step A: Synthesis of 4-fluoro-Ar-Ic/y-4-(4-methyl-quinolin-2-yIamino)-cyclohexyIl-
benzamide hydrochloride.
Using the procedure for the step B of example 3070, the title compound was obtained.
ESI MS m/e 378, M (free)+ H+;'HNMR (300 MHz, CDC13) 5 1.81-2.10 (m, 8 H), 2.72 (s, 3 H),
3.95-4.29 (m, 2 H), 6.65-6.81 (m, 2 H), 7.10 (t, J~ 8.6 Hz, 2 H), 7.42-7.51 (m, 1 H), 7.67-7.91 (m,
5 H), 9.55-9.67 (m, 1 H).

706
Example 3170
3-Fluoro-Ar-[ci5-4-(4-methyl-quino1in-2-ylamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 3-Fluoro-Ar-[cw-4-(4-methyl-quinoIin-2-yIamino)-cyclohexyl]-
benzamide hydrochloride.
Using the procedure for the step B of example 3070, the title compound was obtained.
ESI MS m/e 378, M (free) + H"; !H NMR (300 MHz, CDC13) 5 1.77-2.09 (m, 8 H), 2.71-2.76 (m, 3
H), 3.94-4.25 (m, 2 H), 6.54-6.65 (m, 1 H), 6.76-6.81 (m, 1 H), 7.13-7.23 (m, 1 H), 7.35-7.61 (m, 4
H), 7.67-7.88 (m, 3 H), 9.58-9.73 (m, 1 H).
Example 3171
2-Fluoro-Af-[c/$-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-benzamide hydrochloride
Step A: Synthesis of 2-Fluoro-iV-|e/.y-4-(4-methyl-quinolin-2-ylaniino)-cyclohexyl]-
benzamide hydrochloride.
Using the procedure for the step B of example 3070, the title compound was obtained.
ESI MS m/e 378, M (free) + H*; ]H NMR (300 MHz, CDCI3) 5 1.84-2.15 (m, 8 H), 2.72 (s, 3 H),
3.87-4.01 (m, 1 H), 4.13-4.29 (m, 1 H), 6.73-6.89 (m, 2 H), 7.07-7.28 (m, 2 H), 7.40-7.51 (m, 2 H),
7.66-7.87 (m, 3 H), 7.96-8.05 (m, 1 H), 9.62-9.72 (m, 1 H).
Example 3172
4-Chloro-AL[cw-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide hydrochloride
Step A: Synthesis of 4-chIoro-7V-[ci5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
benzamide hydrochloride.
Using the procedure for the step B of example 3070, the title compound was obtained.

707
ESI MS m/e 394, M (free) + H+; !H NMR (300 MHz, DMSO-d6) 5 1.64-2.04 (m, 8 H), 2.55-2.70 (m,
3 H), 3.87-4.04 (m, 1 H), 4.27-4.52 (m, 1 H), 7.07-7.18 (m, 1 H), 7.46-7.58 (m, 3 H), 7.73-8.02 (m,
4 H), 8.23-8.38 (m, 2 H), 9.39-9.52 (m, 1 H), 12.96-13.10 (m, 1 H).
Example 3173
2-Hydroxy-Ar-[cw-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyl]-nicotinamide hydrochloride
Step A: Synthesis of 2-Hydroxy-Ar-[C1-5>-4-(4-methyl-quinolin-2-ylamino)-cyclohexylJ-
nicotinamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 399, M (free) + Na+; ]H NMR (300 MHz, DMSO-d6) 5 1.46-1.99 (m, 8 H), 2.53-2.72 (m,
3 H), 4.02-4.15 (m, 1 H), 4.20-4.45 (m, 1 H), 6.46-6.56 (m, 1 H), 6.95-7.08 (m, 1 H), 7.45-7.57 (m,
I H), 7.69-7.83 (m, 2 H), 7.90-8.47 (m, 3 H), 10.08-10.27 (m, 1 H), 12.48-12.63 (m, 1 H).
Example 3174
Ar-[C1-5-4-(4-Methyl-quinolin-2-ylamino)-cyclohexyl]-isophthalamic acid-methyl ester
hydrochloride
Step A: Synthesis of 7V-[c/$-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-isophthalamic acid
methyl ester hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 440, M (free) + Na+; ]H NMR (300 MHz, CDC13) 5 1.78-2.21 (m, 8 H), 2.73 (d, 7=1.1
Hz, 3 H), 3.92-4.07 (m, 4 H), 4.13-4.29 (m, 1 H), 6.78 (s, 1 H), 6.99-7.10 (m, 1 H), 7.40-7.57 (m, 2
H), 7.67-7.79 (m, 2 H), 7.82-7.89 (m, 1 H), 8.02-8.19 (m, 2 H), 8.46-8.52 (m, 1 H), 9.46-9.65 (m, 1
H).

708
Example 3175
6-Chloro-iV-[c/s-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide hydrochloride
Step A: Synthesis of 6-chloro-Ar-[c«-4-(4-methyl-quinolin-2-yIamino)-cyclohexyl]-
nicotinamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 417, M (free) + Na+; lH NMR (300 MHz, DMSO-d6) 5 1.67-2.03 (m, 8 H), 2.54-2.72 (m,
3 H), 3.91-4.06 (m, 1 H), 4.26-4.42 (m, 1 H), 7.05-7.18 (m, 1 H), 7.45-7.57 (m, 1 H), 7.63-7.69 (m,
1 H), 7.73-7.83 (m, 1 H), 7.91-8.04 (m, 1 H), 8.17-8.31 (m, 2 H), 8.51-8.62 (m, 1 H), 8.83-8.89 (m,
1 H), 9.33-9.51 (m, 1 H), 12.86-13.03 (m, 1 H).
Example 3176
6-Dimethylamino-AL[ci5-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-nicotinamide
dihydrochloride
Step A: Synthesis of 6-dimethylamino-AL[cK-4-(4-methyl-quinolin-2-yIamino)-cyclohexylJ-
nicotinamide dihydrochloride.
To a solution of 6-chloro-Ar-[cw-4-(4-methyl-quinolin-2-yIamino)-cyclohexyl]-
nicotinamide obtained in step A of example 3175 (250 mg) in IPA (1 mL) were added 50%
aqueous Me2NH (63 mg) and iPr^NEt (172 mg). The mixture was stirred at reflux for 5 hr,
added 50% aqueous Me2NH (120 mg), and stirred at reflux for 5 hr. The reaction was
quenched with saturated aqueous NaHCC>3 and the aqueous layer was extracted with CHCI3
(three times). The combined organic layer was dried over MgSC>4, filtrated, concentrated
under reduced pressure, and purified by medium-pressure liquid chromatography (NH-silica
gel, EtOAc). To a solution of the above material in EtOH (3 mL) was added 4 M hydrogen
chloride in EtOAc (0.47 mL). The mixture was stirred at ambient temperature for 1 hr and

709
concentrated under reduced pressure. A suspension of the above material in Et^O (3 mL)
was stirred at ambient tempareture for 4 hr. The precipitate was collected by filtration,
washed with Et2O, and dried under reduced pressure to give 6-dimethylarnino-/V-[c*s-4-
(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide dihydrochloride (200 mg) as a
white solid.
ESI MS m/e 426, M (free) + Na+; 'H NMR (300 MHz, CDC13) 5 1.73-2.13 (m, 8 H), 2.63-2.80 (m,
3 H), 3.34-3.61 (m, 6 H), 3.91-4.28 (m, 2 H), 6.70-7.07 (m, 2 H), 7.35-8.10 (m, 5 H), 8.29-8.46 (m,
1 H), 8.82-8.98 (m, 1 H), 9.36-9.51 (m, 1 H).
Example 3177
3-Hydroxymethyl-A'-[cw-4-(4-methyl-quinolin-2-ylainino)-cyclohexyI]-ben2ainide
hydrochloride
Step A: Synthesis of 3-hydroxymethyl-7V-[c/s-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
benzamide hydrochloride.
To a suspension of LiAlH (18 mg) in Et2O (5 mL) was added iV-[c/s-4-(4-methyl-quinoIin-
2-ylamino)-cyclohexyl]-isophthaIamic acid methyl ester obtained in step A of example 3174 (200 mg)
in Et2O (2 mL). The mixture was stirred at ambient temperature for 3 hr. The reaction was quenched
with water and the aqueous layer was extracted with CHC13 (three times). The combined organic layer
was dried over MgSO4, filtrated, concentrated under reduced pressure and purified by
medium-pressure liquid chromatography (silica gel, 3% to 10% MeOH in CHC13). To a solution of
the above material in EtOH (2 mL) was added 4 M hydrogen chloride in EtOAc (0.24 mL). The
mixture was stirred at ambient temperature for 2 hr and concentrated under reduced pressure. A
suspension of the above material in Et2O (3 mL) was stirred at ambient tempareture for 1 hr. The
precipitate was collected by filtration, washed with Et2O, and dried at 70 °C under reduced pressure to
give 3-hydroxymethyl-N-[c/5-4-(4-methyi-quinolin-2-ylamino)-cyclohexyll-benzamide
hydrochloride (93 mg) as a white solid.

710
ESI MS m/e 390, M (free) + H+; 'H NMR (300 MHz, DMSO-d6) 6 1.66-2.02 (m, 8 H), 2.61 (s, 3 H),
3.87 (brs, 1 H), 4.22-4.42 (m, 1 H), 4.55 (s, 2 H), 7.03-7.17 (m, 1 H), 7.35-7.59 (m, 3 H), 7.67-7.87
(m, 3 H), 7.91-8.04 (m, 1 H), 8.11-8.31 (m, 2 H), 12.75-12.96 (m, 1 H).
Example 3178
Ar-[c/y-4-(4-Methyl-quinolin-2-ylamino)-cyclohexyl]-isophthalamide hydrochloride
Step A: Synthesis of 7V-[c«-4-(4-methyl-quinolin-2-ylainino)-cyclohexyl]-isophthalaniic acid
methyl ester.
To a solution of isophthalic acid monomethyl ester (400 mg) and iV-(ci.y-4-methyI-
quinolin-2-yl)-cyclohexane-l,4-diamine in step A of example 3070 (400 mg) in DMF (4 mL) were
added Et3N (0.52 mL), HOBt-H2O (358 mg), and EDC-HC1 (330 mg). The reaction mixture was
stirred at ambient temperature for 12 hr. To the reaction mixture was added water (20 mL) and the
suspension was stirred at ambient temperature for 30 min. The precipitated was collected by filtration,
washed with H2O, and purified by medium-pressure liquid chromatography (silica gel, 9% MeOH in
CHCI3) to give jV-[c/5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-isophthalamic acid methyl ester
(740 mg) as a white solid.
ESI MS m/e 440, M + Na+; ]H NMR (200 MHz, CDC13) 5 1.59-2.09 (m, 8 H), 2.58 (s, 3 H), 3.96 (s,
3 H), 4.02-4.29 (m, 2 H), 4.72-4.87 (m, 1 H), 6.12-6.27 (m, 1 H), 6.48-6.59 (m, 1 H), 7.17-7.30 (m,
1 H), 7.45-7.82 (m, 4 H), 8.00-8.22 (m, 2 H), 8.32-8.39 (m, I H).
Step B: Synthesis of iV-[ci5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-isophthalamide
hydrochloride.
To a solution of A^-[c/5-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-
isophthalamic acid methyl ester (150 mg) in EtOH (4.5 mL) was added 2 M aqueous NaOH
(0.27 mL). The reaction mixture was stirred at ambient temperature for 13 hr. To the reaction mixture
was added 1 M aqueous HC1 (0.3 mL) and the aqueous layer was extracted with CHC13 (three times).

711
The combined organic layer was dried over MgSO4, filtered, concentrated under reduced pressure,
purified by medium-pressure liquid chromatography (silica gel, 1% to 5% MeOH in CHCi3) to give
a white solid. To a solution of the above solid in DMF (2 mL) was added 28% aqueous NH3 (21 mg),
Et3N (0.1 mL), HOBt-H2O (67 mg), and EDC-HC1 (67 mg). The reaction mixture was stirred at
ambient temperature for 12 hr. To the reaction mixture was added water (20 mL) and the aqueous
layer was extracted with CHCI3 (three times). The combined organic layer was dried over MgSO4,
filtered, concentrated under reduced pressure, purified by medium-pressure liquid chromatography
(NH-silica gel, 3% to 9% MeOH in CHC13). The solution of above material in EtOAc (10 mL) was
added 4 M hydrogen chloride in EtOAc (0.2 mL). The mixture was stirred at ambient temperature for
I hr and concentrated under reduced pressure. A suspension of the above material in Et2O (12 mL)
was stirred at ambient tempareture for 2 hr. The precipitate was collected by filtration, washed with
Et2O, and under reduced pressure to give Ar-[cj5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
isophthalamide hydrochloride
ESI MS m/e 403, M (free) + H+; ]H NMR (300 MHz, DMSO-d6) 5 1.69-2.04 (m, 8 H), 2.56-2.63 (m,
3 H), 3.92-4.06 (m, 1 H), 4.28-4.48 (m, 1 H), 7.06-7.17 (m, 1 H), 7.41-7.58 (m, 3 H), 7.70-8.04 (m,
3 H), 8.06-8.43 (m, 3 H), 9.35-9.54 (m, 1 H), 12.87-13.07 (m, 1 H).
Example 3179
3-Chloro-5-fluoro-Ar-[C1-5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide
hydrochloride
Step A: Synthesis of 3-chloro-5-fluoro-Ar-[ci*-4-(4-methyl-quinolin-2-ylamino)-
cyclohexylj-benzamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 412, M (free) + H+; ]H NMR (300 MHz, CDCI3) 5 1.79-2.12 (m, 8 H), 2.73 (d, J= 0.9
Hz, 3 H), 3.96-4.22 (m, 2 H), 6.75-6.90 (m, 2 H), 7.17-7.25 (m, 1 H), 7.42-7.51 (m, 2 H), 7.59-7.89
(m, 4 H), 9.51-9.72 (m, 1 H).

712
Example 3180
3,4,5-Trinuoro-Ar-[C1-5-4-(4-inethyl-quinolin-2-ylamino)-cyclohexyI]-benzamidehydrochloride
Step A: Synthesis of 3,4,5-trifluoro-Af-[c/.y-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-benzamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESIMSm/e414,M(free) + H+; lHNMR (300 MHz, CDC13) 8 1.76-2.16 (m, 8 H), 2.73 (d, J= 1.1
Hz, 3 H), 3.97-4.24 (m, 2 H), 6.78 (s, \ H), 6.92-7.04 (m, 1 H), 7.41-7.60 (m, 3 H), 7.68-7.77 (m, 2
H), 7.82-7.89 (m, I H), 9.50-9.64 (m, 1 H).
Example 3181
Pyridine-2-carboxylic acid [c/y-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-amide
hydrochloride
Step A: Synthesis of pyridine-2-carboxylic acid [c/s"-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-amide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 383, M (free) + Na+; ]HNMR (300 MHz, DMSO-d6) 5 1.63-2.07 (m, 8 H), 2.54-2.71 (m,
3 H), 4.00-4.13 (m, 1 H), 4.49-4.62 (m, 1 H), 7.10-7.20 (m, 1 H), 7.46-7.56 (m, 1 H), 7.61-8.12 (m,
5 H), 8.33-8.42 (m, 2 H), 8.65-8.72 (m, 1 H), 9.46-9.60 (m, 1 H), 13.23-13.38 (m, 1 H).
Example 3182
7V-[c/$-4-(4-Methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide hydrochloride

713
Step A: Synthesis of Ar-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyC1-5hexyl]-
nicotinamide hydrochloride.
Using the procedure for the step A of example 3 071, the title compound was obtained.
ESI MS m/e 383, M (free) + Na+; 'H NMR (300 MHz, DMSO-d6) 5 1.76-2.05 (m, 8 H), 2.54-2.73 (m,
3 H), 3.93-4.07 (m, 1 H), 4.29-4.48 (m, 1 H), 7.10-7.19 (m, 1 H), 7.47-7.57 (m, 1 H), 7.72-7.85 (m,
2 H), 7.92-8.04 (m, 1 H), 8.21-8.33 (m, 1 H), 8.48-8.57 (m, 1 H), 8.65-8.73 (m, 1 H), 8.82-8.89 (m,
1 H), 9.14-9.20 (m, 1 H), 9.42-9.58 (m, 1 H), 12.93-13.08 (m, 1 H).
Example 3183
Ar-[cw-4-(4-Methyl-quinolin-2-ylamino)-cyclohexyl]-isonicotinamide hydrochloride
Step A: Synthesis of Ar-[c/y-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-isonicotinamide
hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 383, M (free) + Na+; *HNMR (300 MHz, DMSO-d6) 5 1.68-2.08 (m, 8 H), 2.53-2.71 (m,
3 H), 3.92-4.08 (m, 1 H), 4.33-4.54 (m, 1 H), 7.11-7.22 (m, 1 H), 7.43-7.60 (m, 1 H), 7.69-7.86 (m,
1 H), 7.89-8.41 (m, 4 H), 8.81-9.07 (m, 3 H), 9.48-9.67 (m, 1 H), 13.03-13.24 (m, 1 H).
Example 3184
4-Chloro-pyridine-2-carboxylic acid [c/s-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-
amide hydrochloride
Step A: Synthesis of 4-Chloro-pyridine-2-carboxylic acid [cw-4-(4-methyl-quinolin-2-
ylamino)-cyclohexyl]-amide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 417, M (free) + Na+; !H NMR (300 MHz, DMSO-d6) 5 1.62-2.05 (m, 8 H), 2.53-2.72 (m,

714
3 H), 3.99-4.51 (m, 2 H), 7.04-7.15 (m, 1 H), 7.46-7.57 (m, 1 H), 7.72-7.85 (m, 2 H), 7.92-8.10 (m,
2 H), 8.16-8.29 (m, 1 H), 8.39 (d, 7= 8.1 Hz, 1 H), 8.66 (d, 7= 5.3 Hz, 1 H), 9.32-9.51 (m, 1 H),
12.93-13.08 (m, 1 H).
Example 3185
5-Bromo-Ar-[c/s-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-iiicotinaniide dihydrochloride
Step A: Synthesis of 5-bromo-Ar-[c/5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
nicotinamide dihydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 439, M (free) + H+; 'H NMR (300 MHz, DMSO-d6) 5 1.71-2.02 (m, 8 H), 2.54-2.71 (m,
3 H), 3.88-4.08 (m, 1 H), 4.25-4.50 (m, 1 H), 7.06-7.18 (m, 1 H), 7.47-7.56 (m, 1 H), 7.70-7.83 (m,
1 H), 7.91-8.04 (m, 1 H), 8.19-8.33 (m, 1 H), 8.43-8.64 (m, 2 H), 8.86-8.88 (m, 1 H), 8.97-8.99 (m,
1 H), 9.35-9.50 (m, 1 H), 12.89-13.08 (m, 1 H).
Example 3186
Ar-[C1-5-4-(4-Methyl-quinolin-2-ylamino)-cyclohexyl]-6-trifluoromethyl-nicotinamide
hydrochloride
Step A: Synthesis of AL[c/5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-6-
trifluoromethyl-nicotinamide hydrochloride.
Using the procedure for the step A of example 3071, the title compound was obtained.
ESI MS m/e 451, M (free) + Na+; lHNMR (300 MHz, DMSO-d6) 8 1.58-2.04 (m, 8 H), 2.53-2.75 (m,
3 H), 3.91-4.09 (m, 1 H), 4.22-4.44 (m, 1 H), 7.03-7.22 (m, 1 H), 7.45-7.59 (m, 1 H), 7.71-7.85 (m,
1 H), 7.91-8.10 (m, 2 H), 8.15-8.30 (m, 1 H), 8.42-8.54 (m, 1 H), 8.64-8.81 (m, 1 H), 9.12-9.21 (m,
1 H), 9.33-9.54 (m, 1 H), 12.88-13.00 (m, 1 H).

715
Example 3187
6-Imidazol-l-yl-yV-[c/s-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-iiicotinamide
dihydrochloride
Step A: Synthesis of 6-imidazol-l-yl-A^-[a5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
nicotinamide dihydrochloride.
To a solution of 6-chloro-Af-[cf5-4-(4-methyI-quinolin-2-ylamino)-cyC1-5hexyl]-
nicotinamide obtained in step A of example 3175 (250 mg) in BuOH (1 mL) were added imidazole
(47 mg)and iPr2NEt (172 mg). The mixture was heated in a microwave synthesizer at 220°C for 10
min and 230°C for 20 min. To the mixture was added saturated aqueous NaHCO3 and the aqueous
layer was extracted with CHC13 (three times). The combined organic layer was dried over MgSO4,
filtrated, concentrated under reduced pressure, and purified by medium-pressure liquid
chromatography (NH-silica gel, 50% in EtOAc in nexane). To a solution of the above material in
EtOAc (10 mL) was added 4 M hydrogen chloride in EtOAc (0.2 mL). The mixture was stirred at
ambient temperature for 1 hr and concentrated under reduced pressure. A suspension of the above
material in Et2O (12 mL) was stirred at ambient tempareture for 4 hr. The precipitate was collected by
filtration, washed with Et2O, and dried under reduced pressure to give
6-imidazol-l-yl-Ar-[c/5-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-nicotinamide dihydrochloride
(83 mg) as a white solid.
ESI MS m/e 427, M (free) + H+; lHNMR (300 MHz, DMSO-d6) 5 1.35-2.39 (m, 8 H), 2.60-2.81 (m,
3 H), 3.92-4.28 (m, 2 H), 6.63-6.92 (m, I H), 7.09-8.23 (m, 8 H), 8.53-8.82 (m, 1 H), 8.95-9.41 (m,
2 H), 9.96-10.17 (m, 1 H), 13.97-14.19 (m, 1 H).
Example 3188
iV-[c/s-4-(4-Dimethylamino-quinolin-2-ylamino)-cyclohexylJ-3,4-difluoro-benzamide

716
hydrochloride
Step A: Synthesis of 7V-[c/s-4-(4-dimethylamino-quinolin-2-ylamino)-cyclohexyl]-
3,4-difluoro-benzamide hydrochloride.
To a solution of 3,4-difluoro-benzoic acid (199 mg) and iV2-(c/.y-4-amino-
cyclohexyI)-yV4-methyI-quinoline-2,4-diamine obtained in step E of example 1 (300 mg) in DMF (3
mL) were added Et3N (0.35 mL), HOBt-H2O (241 mg), and EDC-HC1 (242 mg). The reaction
mixture was stirred at ambient temperature for 15 hr. To the mixture was added water (4.8 mL) and
the aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over
MgSO4, filtered, concentrated under reduced pressure, and purified by medium-pressure liquid
chromatography (NH-silica gel, 20% EtOAc in hexane). To a solution of the above material in EtOAc
(4 mL) was added 4 M hydrogen chloride in EtOAc (0.5 mL). The mixture was stirred at ambient
temperature for 1 hr. The precipitate was collected by filtration, washed with EtOAc, and dried under
reduced pressure to give Ar-[cf5-4-(4-dimethylamino-quinolin-2-yIamino)-cyC1-5hexyl]-3,4-difluoro-
benzamide hydrochloride (263 mg) as a white solid.
ESI MS m/e 425, M (free) + H+; !H NMR (300 MHz, CDC13) 5 1.69-2.20 (m, 8 H), 3.24 (s, 6 H),
3.81-4.30 (m, 2 H), 5.82 (s, 1 H), 6.74-6.88 (m, 1 H), 7.10-7.40 (m, 2 H), 7.51-7.98 (m, 5 H),
8.86-8.99 (m, 1 H), 13.44-13.63 (m, 1 H).
Example 3189
5-Nitro-thiophene-3-carboxylicacid [d5-4-(4-dimethylamino-quinoIin-2-ylamino)-
cyclohexyl]-amide hydrochloride
Step A: Synthesis of 5-nitro-thiophene-3-carboxylic acid [as-4-(4-dimethylamino-quinolin-2-
ylamino)-cyclohexyl]-amide hydrochloride.
Using the procedure for the step A of example 3188, the title compound was obtained.
ESI MS m/e 462, M (free) + Na+; lH NMR (300 MHz, CDCl3) 5 1.65-2.17 (m, 8 H), 3.25 (s, 6 H),

717
3.82-4.00 (m, 1 H), 4.00-4.23 (m, 1 H), 5.82 (s, 1 H), 7.25-7.40 (m, 1 H), 7.58-7.97 (m, 4 H) 8.28-8.42
(m, 2 H), 8.56-8.73 (m, 1 H), 13.02-13.30 (m, 1 H).
Example 3190
Ar-[ci5-4-(4-Dimethylamino-quirtolin-2-ylainino)-cyclohexylinethyl]-3,4-difluoro-benzainide
hydrochloride
Step A: Synthesis of AL[cw-4-(4-dimethylamino-quinolin-2-ylamino)-cyclohexylmethyll-
3,4-difluoro-benzamide hydrochloride.
To a solution of A'2-(£7w-4-aminomethyl-cyC1-5hexyl)-Af4,A'4-dimethyl-quinoline-2,4-diamine
obtained in step B of example 7 (300 mg) in CHC13 (3 mL) were added iPr2NEt (0.36 mL) and
3,4-difluoro-benzoyl chloride (194 mg). The mixture was stirred at ambient temperature for 6 hr. The
reaction was quenched with saturated aqueous NaHCO3 and the aqueous layer was extracted with
CHCI3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated under
reduced pressure, and purified by medium-pressure liquid chromatography (NH-silica gel, 9% to 20%
EtOAc in hexane and 2% to 9% MeOH in CHCI3) to give iV-[cw-4-(4-dimethylamino-quinoIin-2-
ylamino)-cyclohexylmethyl]-3,4-difluoro-benzarnide hydrochloride (272 mg) as white solid.
ESI MS m/e 439, M (free) + H"; !H NMR (300 MHz, CDC13) 8 1.53-2.08 (m, 9 H), 3.21 (s, 6 H),
3.47-3.56 (m, 2 H), 3.86-3.98 (rn, I H), 5.81 (s, 1 H), 6.95-7.09 (m, 1 H), 7.16-7.34 (m, 2 H),
7.53-7.68 (m, 2 H), 7.80-7.95 (m, 3 H), 9.08-9.22 (m, 1 H), 13.40-13.51 (m, 1 H).
Example 3191
l-(2^-Dichloro-phenyl)-3-[c/y-4-(4-dimethylamino-quinolin-2-ylamino)-cyclohexylmethyl]-
urea hydrochloride
Step A: Synthesis of l-(23-dichloro-phenyI)-3-[cw-4-(4-dimethylamino-quinolin-2-

718
ylamino)-cycfohexylmethyl]-urea hydrochloride.
To a solution of A^-(c/5-4-aminomethyl-cyclohexyl)-7V4TA/4-dimethyl-quinoline-2,4-diamine
obtained in step B of example 7 (300 mg) in DMSO (3 mL) was added l,2-dichIoro-4-isocyanato-
benzene (207 mg). The mixture was stirred at ambient temperature for 12 hr and poured into water.
The precipitate was filtrated, washed with water, and purified by medium-pressure liquid
chromatography (NH-silica gel, 25% to 50% EtOAc in hexane). To a solution of the above material
in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at
ambient temperature for 1 hr and concentrated under reduced pressure. A suspension of the residue
in Et2O (20 mL) was stirred at ambient tempareture for 1 hr. The precipitate was collected by filtration,
washed with Et2O, and dried under reduced pressure to give
l-(2,3-dichloro-phenyl)-3-[c/5-4-(4-dimethyiamino-quinolin-2-ylamino)-cyclohexylmethyl]-urea
hydrochloride (170 mg) as a white solid.
ESI MS m/e486, M+; 'HNMR (300 MHZ, CDC13) 6 1.51-2.18 (m, 9 H), 3.23 (s, 6 H), 3.36-3.44 (m,
2 H), 3.91-4.02 (m, 1 H), 5.78-5.88 (m, I H), 6.97-7.12 (m, 3 H), 7.26-7.35 (m, 1 H), 7.58-7.66 (m,
1 H), 7.86 (m, .7=9.0 Hz, 2 H), 8.16 (dd,y= 8.2, 1.7 Hz, 1 H), 8.20-8.31 (m, 1 H), 8.65-8.76 (m, 1
H), 12.98-13.21 (m, 1 H).
Example 3192
AL[c/$-4-(4-dimethylaminO"5,6,7,8-tetrahydro-quinazolin-2-ylainino)-cyclohexyl]-3,4-difluoro-
benzamide hydrochloride
Step A: Synthesis of jV-[cw-4-(4-dimethylamino-5,6,7,8-tetrahydro-quinazolin-2-
ylaniino)-cyclohexyl]-3,4-difluoro-benzamide hydrochloride.
To a solution of 3,4-difluoro-benzoic acid (199 mg) and 7V2-(ds-4-amino-cyclohexyl)-
A^^-dimethyl-S^J^-tetrahydro-quinazoIine^^-diamine in step D of example 3107 (304 mg) in
DMF (4 mL) were added Et3N (0.35 mL), HOBt-H2O (241 mg), and EDC-HC1 (242 mg). The
reaction mixture was stirred at ambient temperature for 7 hr. To the reaction mixture was added water

719
(20 mL) and the suspension was stirred at ambient temperature for 1 hr. The precipitated was collected
by filtration, washed with H?O, and purified by medium-pressure liquid chromatography (NH-silica
gel, 20% EtOAc in hexane). To a solution of the above material in EtOAc (10 mL) was added 4 M
hydrogen chloride in EtOAc (0.2 mL). The mixture was stirred at ambient temperature for 1 hr. The
precipitate was collected by filtration, washed with EtOAc, and dried under reduced pressure to give
A^[cw-4-(4-dimethylamino-5,6,7,8-tetrahydro-quinazoIin-2-ylamino)-
cyclohexyl]-3,4-difiuoro-benzamide hydrochloride (252 mg) as a white solid.
ESI MS m/e 430, M (free) + H+; *H NMR (300 MHz, CDC13) 5 1.56-2.22 (m, 12 H), 2.48-2.84 (m,
4 H), 3.23 (s, 6 H), 3.92-4.33 (m, 2 H), 6.51-6.77 (m, 1 H), 7.01-7.30 (m, 1 H), 7.43-7.86 (m, 2 H),
8.28-8.57 (m, 1 H), 12.56 (m, 1 H).
Example 3193
5-Nitro-thiophene-3-carboxylic acid [C1-5-4-(4-dimethylamino-5,6,7,8-tetrahydro-quinazolin-
2-ylamino)-cyclohexyl]-amide hydrochloride
Step A: Synthesis of 5-nitro-thiophene-3-carboxylic acid [c/s-4-(4-dimethylamino-5,6,7,8-
tetrahydro-quinazolin-2-ylamino)-cyclohexyl]-amide hydrochloride.
Using the procedure for the step A of example 3192, the title compound was obtained.
ESI MS m/e 467, M (free) + Na+; !H NMR (300 MHz, CDC13) 5 1.51-2.24 (m, 12 H), 2.51-2.62 (m,
2 H), 2.67-2.81 (m, 2 H), 3.23 (s, 6 H), 3.98-4.29 (m, 2 H), 7.42-7.48 (m, 1 H), 8.22-8.29 (m, 2 H),
8.37 (s, 1 H).
Example 3194
l-Methyl-4-nitro-l/7-pyrrole-2-carboxyHc acid [cw-4-(4-dimethylamino-5,6,7,8-
tetrahydro-quinazoIin-2-ylamino)-cyclohexyl]-amide hydrochloride

720
Step A: Synthesis of l-methyl~4-nitro-l//-pyrrole-2-carboxylic acid [c/s-4-(4-dimethylamino-
5,6,7,8-tetrahydro-quinazolm-2-yIamino)-cyclohexyl]-amide hydrochloride
Using the procedure for the step A of example 3192, the title compound was obtained.
ESI MS m/e 442, M (free) + H+; !H NMR (300 MHz, CDC13) 5 1.57-2.13 (m, 12 H), 2.49-2.61 (m,
2 H), 2.68-2.81 (m, 2 H), 3.22 (s, 6 H), 3.93-4.04 (m, 4 H), 4.14-4.24 (m, 1 H), 7.04-7.12 (m, 1 H),
7.23-7.27 (m, 1 H), 7.49-7.54 (m, I H), 8.30-8.41 (m, 1 H), 12.66-12.92 (m, 1 H).
Example 3195
AL[c/s-4-(4-Dimethylamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-cyclohexylmethyl]-
3,4-difluoro-benzamide hydrochloride
Step A: Synthesis of iV-[c/5-4-(4-dimethylamino-5,6,7,8-tetrahydro-quinazoIin-2-yIamino)-
cyclohexylm ethyl]-3,4-difluoro-benza mid e hydrochloride.
To a solution of A^-tc/i^-aminomethyl-cyclohexyO-A^^-dimethyl-S^J.S-tetrahydro-
quinazoline-2,4-diamine in step A of example 3113 (300 mg) in CHCI3 (3 mL) were added iPr2NEt
(0.36 mL) and 3,4-difluoro-benzoyl chloride (194 mg). The mixture was stirred at ambient
temperature for 17 hr. The reaction was quenched with saturated aqueous NaHCC>3 and the aqueous
layer was extracted with CHC13 (three times). The combined organic layer was dried over MgSO4,
filtered, concentrated under reduced pressure, and purified by medium-pressure liquid
chromatography (NH-silica gel, 33% EtOAc in hexane). To a solution of the above material in EtOAc
(2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient
temperature for 1 hr and concentrated under reduced pressure. A suspension of the residue in Et2O
(20 mL) was stirred at ambient tempareture for 1 hr. The precipitate was collected by filtration,
washed with Et2O, and dried under reduced pressure to give Ar-[cw-4-(4-dimethylamino-5,6,7,8-
tetrahydro-quinazolin-2-ylamino)-cyclohexylmethyl]-3?4-difluoro-benzamidehydrochforide (263
mg) as a white solid.
ESI MS m/e 466, M (free) + Na+; 'H NMR (300 MHz, CDC13) 5 1.50-1.96 (m, 13 H), 2.49-2.59 (m,

721
2 H), 2.66-2.77 (m, 2 H), 3.21 (s, 6 H), 3.42-3.51 (m, 2 H), 4.16-4.28 (m, 1 H), 6.91-7.01 (m, 1 H),
7.17-7.26 (m, 1 H), 7.80-7.92 (m, 2 H), 8.55 (d,J= 8.2 Hz, 1 H), 12.61-12.77 (m, 1 H).
Example 3196
l-(2r3-Dichloro-phenyl)-3-[cw-4-(4-dimethylamino-5,6,7,8-tetrahydro-quinazolin-2-yIaiiiino)-
cyclohexylmethyl]-urea hydrochloride
Step A: Synthesis of l-(2,3-dichIoro-phenyl)-3-[cw-4-(4-dimethylamino-5,6,7,8~tetrahydro-
quinazolin~2-ylamino)-cyclohexylmethyl]-urea hydrochloride.
To a solution of A^-fc/^^-aminomethyl-cyclohexy^-TV^^-dimethyl-S^^^-tetrahydro-
quinazoline-2,4-diamine in step A of example 3113 (300 mg) in DMSO (3 mL) was added
l,2-dichloro-4-isocyanato-benzene (207 mg). The mixture was stirred at ambient temperature for 12
hr and poured into water. The precipitate was filtrated, washed with water, and purified by
medium-pressure liquid chromatography (NH-silica gel, 25% to 50% EtOAc in hexane). To a
solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL).
The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure. A
suspension of the residue in Et2O (20 mL) was stirred at ambient tempareture for 1 hr. The precipitate
was collected by filtration, washed with Et2O, and dried under reduced pressure to give l-(2,3-
dichIoro-phenyl)-3-[f^-4-(4-dimethyIamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)-
cyclohexyimethyl]-urea hydrochloride (113 mg) as a white solid.
ESI MS m/e 491, M+; 'H NMR (200 MHz, CDC13) 5 1.42-2.04 (m, 13 H), 2.46-2.80 (m, 4 H), 3.21
(s, 6 H), 3.29-3.44 (m, 2 H), 4.18-4.38 (m, 1 H), 6.80-7.22 (m, 3 H), 8.06-8.45 (m, 3 H), 12.04-12.29
(m, 1 H).
Example 3197
A^-[c/5-4-(4-Dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-3,4-difluoro-benzamide

722
hydrochloride
Step A: Synthesis of A^cw-4-(4-dimethylamino~pyrimidin-2-ylamino)-cyC1-5hexyl]-
3,4-difluoro-benzamide hydrochloride.
Using the procedure for the step D of example 3129, the title compound was obtained.
ESI MS m/e 376, M (free)+ H+;JHNMR(300 MHz, CDCI3) 6 1.61-2.01 (m, 8 H), 3.17 (s, 3 H)s 3.28
(s, 3 H), 3.98-4.32 (m, 2 H), 5.98 (d,J= 7.3 Hz, 1 H), 6.45-6.63 (m, 1 H), 7.11-7.30 (m, 1 H),
7.41-7.79 (m, 3 H), 8.67-8.94 (m, 1 H), 12.89-13.06 (m, 1 H).
Example 3198
5-Nitro-thiophene-3-carboxylic acid [c/s-4-(4-dimethylamino-pyrimidine-2-ylamino)-
cyclohexyl]-amide hydrochloride
Step A: Synthesis of 5-nitro-thiophene-3-carboxylic acid [cis-4-(4-dimethylamino-
pyrimidine-2-ylamino)-cyclohexyl]~amide hydrochloride.
To a solution of 5-nitro-thiophene-3-carboxylic acid (265 mg) and cis-N2-(4-am'mo-
cyclohexyl)-A^V-dimethyl-pyrirnidine-2,4-diamine in step C of example 3129 (300 mg) in DMF (3
mL) were added Et3N (0.43 mL), HOBt-H2O (293 mg), and EDC-HC1 (293 mg). The reaction
mixture was stirred at ambient temperature for 12 hr. To the reaction mixture was added water (20
mL) and the suspension was stirred at ambient temperature for 1 hr. The precipitated was collected by
filtration, washed with H?O, and purified by medium-pressure liquid chromatography (NH-silica gel,
20% to 50% EtOAc in hexane). To a solution of the above material in EtOAc (10 mL) was added 4
M hydrogen chloride in EtOAc (2 mL). The mixture was stirred at ambient temperature for 1 hr. The
precipitate was collected by filtration, washed with EtOAc, and dried under reduced pressure to give
5-nitro-thiophene-3-carboxylic acid [ci5-4-(4-dimethyIarnino-pyrimidine-2-ylamino)-
cyclohexylj-amide hydrochloride (71 mg) as a white solid.
ESI MS m/e 413, M (free) + Na+; 'HNMR (300 MHz, CDC13) 5 1.62-2.02 (m, 8 H), 3.18 (s, 3 H),

723
3.27 (s, 3 H), 3.99-4.29 (m, 2 H) 5.99 (d, .7=7.5 Hz, 1 H), 7.48-7.64 (m, 2 H), 8.34 (d, J= 1.8 Hz, 1
H), 8.48 (d, 7=1.8 Hz, 1 H), 8.50-8.67 (m, 1 H), 12.58-12.76 (m, 1 H).
Example 3199
5-(4-Chloro-phenyl)-furan-2-carboxylicacid [c/s-4-(4-dimethyIamino-pyrimidin-
2-ylamino)-cyclohexyl]-amide hydrochloride
Step A: Synthesis of 5-(4~Chloro-phenyl)-furan-2-carboxylic acid [c«-4-(4-dimethylamino-
pyrimidin-2-ylamino)-cyclohexyl]-amide hydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e 462, M (free) + Na+; 'H NMR (300 MHz, CDC13) 5 1.67-2.07 (m, 8 H), 3.17 (s, 3 H),
3.28 (s, 3 H), 4.01-4.27 (m, 2 H), 5.97 (d,J= 6.9 Hz, 1 H), 6.71 (d, J= 3.5 Hz, 1 H), 6.76-6.87 (m,
1 H), 7.17 (d, J= 3.5 Hz, 1 H), 7.36-7.55 (m, 3 H), 7.69-7.79 (m, 2 H), 8.65-8.86 (m, 1 H),
13.08-13.30 (m, 1 H).
Example 3200
4'-Fluoro-biphenyl-4-carboxylic acid [c/s-4-(4-dimethyIamino-pyrimidin-2~ylamino)-
cyclohexylj-amide hydrochloride
Step A: Synthesis of 4'-iluoro-biphenyl-4-carboxylic acid [m-4-(4-dimethylamino-pyrimidin-
2-ylamino)-cyclohexyl]-amide hydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e 456, M (free) + Na+; 'H NMR (300 MHz, CDC13) 8 1.66-2.06 (m, 8 H), 3.17 (s, 3 H),
3.28 (s, 3 H), 4.06-4.32 (m, 2 H), 5.97 (d,J= 7.3 Hz, 1 H), 6.50-6.60 (m, 1 H), 7.09-7.20 (m, 2 H),
7.43-7.64 (m, 5 H), 7.85-7.91 (m, 2 H), 8.74-8.86 (m, 1 H), 12.98-13.23 (m, 1 H).

724
Example 3201
7V-[C1-5-4-(4-Dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-2-(4-fluoro-phenoxy)-
nicotinamide hydrochloride
Step A: Synthesis of Ar-[a5-4-(4-dimethylamino-pyriniidin-2-ylamino)-cyclohexyl]-
2-(4-fluoro-phenoxy)-nicotinamide hydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e 473, M (free) + Na+; lH NMR (300 MHz, CDC13) 5 1.62-2.05 (m, 8 H), 3.16 (s, 3 H),
3.26 (s, 3 H), 4.07-4.24 (m, 2 H), 5.94 (d, J= 7.3 Hz, 1 H), 7.09-7.20 (m, 3 H), 7.23-7.32 (m, 2 H),
7.42-7.52 (m, 1 H), 7.81-7.94 (m, 1 H), 8.20 (dd, J= 4.8, 2.0 Hz, 1 H), 8.54 (dd,J= 7.5, 2.1 Hz, 1
H), 8.70-8.80 (m, 1 H), 13.23-13.38 (m, 1 H).
Example 3202
Ar-[c/s-4-(4-Dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-C-(ethyl-phenyl-amino)-
acetamide dihydrochloride
Step A: Synthesis of 7V-[C1-5-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-
C-(ethyl-phenyl-amino)-acetamide dihydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e 419, M (free) + Na+; 'HNMR (300 MHz, CDC13) 5 1.14-1.35 (m, 3 H), 1.55-1.92 (m,
8 H), 3.15 (s, 3 H), 3.24 (s, 3 H), 3.45-3.64 (m, 2 H), 3.75-4.06 (m, 4 H), 5.91-6.03 (m, 1 H), 7.00-7.64
(m, 7 H), 8.32-8.48 (m, 1 H), 13.12-13.34 (m, 1 H).
Example 3203
C-[ci5-(4-Chloro-phenyl)-ethy]-amino]-N-14-(4-dimethylamino-pyrimidin-2-ylamino)-

725
cyclohexylj-acetamide dihydrochloride
Step A: Synthesis of C-[c«-(4-chloro-phenyl)-ethyl-amino]-N-[4-(4-dimethylamino-pyrimidin-
2-ylamino)-cyclohexyl]-acetamide dihydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e 431, M (free)+ H+;1HNMR (300 MHz, CDC13) 5 1.12-1.24 (m, 3 H), 1.51-1.96 (m, 8
H), 3.15 (s, 3 H), 3.25 (s, 3 H), 3.43-3.55 (m, 2 H), 3.74-3.98 (m, 3 H), 4.01-4.18 (m, I H), 5.88-6.02
(m, 1 H), 6.68-6.87 (m, 3 H), 7.15-7.24 (m, 2 H), 7.43-7.52 (m, 1 H), 8.49-8.62 (m, 1 H), 13.11-13.28
(m, 1 H).
Example 3204
2-(3,4-Difluoro-phenyl)-7V-[C1-5-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-
acetamide hydrochloride
Step A: Synthesis of 2-(3,4-difluoro-phenyl)-Ar-[cw-4-(4-dimethyIamino-pyrimidin-
2-y lam in o)-cyclohexy I]-acetamide hydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e 390, M (free) + H+; 'HNMR (300 MHz, DMSO-d6) 5 1.46-1.87 (m, 8 H), 3.15 (s, 3 H),
3.18 (s, 3 H), 3.46 (s, 2 H), 3.58-3.75 (m, 1 H), 3.86-4.04 (m, 1 H), 6.36 (d, J= 1A Hz, 1 H), 7.05-7.13
(m, 1 H), 7.27-7.40 (m, 2 H), 7.84-7.94 (m, 1 H), 8.10-8.19 (m, 1 H), 8.27-8.38 (m, 1 H), 12.14-12.23
(m, I H).
Example 3205
7V-[cis-4-(4-Dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-3,5-difluoro-benzamide
hydrochloride

726
Step A: Synthesis of ^-[c/.M-^-dimethylamino-pyrimidin^-ylamino^cyclohexyl]-
3,5-difluoro-benzamide hydrochloride.
Using the procedure for the step D of example 3129, the title compound was obtained.
ESI MS m/e 376, M (free) + H+; 'HNMR (300 MHz, CDCI3) 5 1.64-2.02 (m, 8 H), 3.17 (s, 3 H), 3.28
(s, 3 H), 4.01-4.31 (m, 2 H), 5.97 (d, J= 7.4 Hz, 1 H), 6.46-6.57 (m, 1 H), 6.87-6.98 (m, 1 H),
7.30-7.40 (m, 2 H), 7.49 (d, J= 7.4 Hz, 1 H), 8.77-8.93 (m, 1 H).
Example 3206
3-Chloro-Ar-[ciy-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-4-fluoro-benzamide
hydrochloride
Step A: Synthesis of 3-Chioro-Ar-[m-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-
4-fluoro-benzamide hydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESIMSm/e392,M(free) + H+;1HNMR(300MHz,CDCl3)5 1.65-2.00(m,SH),3.17(s,3H),3.28
(s, 3 H), 4.03-4.30 (m, 2 H), 5.97 (d, J = 7.5 Hz, 1 H), 6.43-6.53 (m, 1 H), 7.19 (t, J= 8.5 Hz, 1 H),
7.43-7.54 (m, 1 H), 7.65-7.75 (m, 1 H), 7.90-7.97 (m, 1 H), 8.76-8.94 (m, 1 H), 12.95-13.14 (m, 1 H).
Example 3207
4-Chloro-7V-[cis-4-(4-dimethyIamino-pyrimidin-2-ylamino)-cyclohexyl]-3-fluoro-benzamide
hydrochloride
Step A: Synthesis of 4-Chloro-Ar-[c/s-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-
3-fluoro-benzamide hydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e 392, M (free) + HT; 'H NMR (300 MHz, DMSO-df,) 5 1.56-1.98 (m, 8 H), 3.05-3.27 (m,

727
6 H), 3.76-4.10 (m, 2 H), 6.37 (d,J= 7.6 Hz, 1 H), 7.65-7.80 (m, 2 H), 7.84-7.97 (m, 2 H), 8.21-8.34
(m, 1 H), 8.39-8.56 (m, 1 H), 12.09-12.27 (m, 1 H).
Example 3208
Pyridine-2-carboxylic acid [C1-5-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclobexyl]-
amide hydrochloride
Step A: Synthesis of pyridine-2-carboxylic acid {c/s-4-(4-dimethylamino-pyrimidin-2-
ylamino)-cyclohexyl]-amide hydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESIMSm/e341,M(free) + H+;iHNMR(300MHz,CDCl3)51.72-2.07(m,8H),3.17(s,3H),3.27
(s, 3 H), 4.02-4.22 (m, 2 H), 5.97 (d, J = 7.4 Hz, 1 H), 7.36-7.55 (m, 2 H), 7.76-7.88 (m, 1 H),
8.10-8.29 (m, 2 H), 8.52-8.70 (m, 2 H).
Example 3209
Ar-[ctf-4-(4-Dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-nicotinamidedihydrochloride
Step A: Synthesis of A^c/s-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyI]-
nicotinamide dihydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e 341, M (free) + H+; 'HNMR (300 MHz, DMSO-d6) 6 1.62-2.03 (m, 8 H), 3.15 (s, 3 H),
3.20 (s, 3 H), 3.83-4.08 (m, 2 H), 637 (d, J= 7.4 Hz, 1 H), 7.81-7.98 (m, 2 H), 8.34-8.48 (m, 1 H),
8.58-8.66 (m, 1 H), 8.76-8.93 (m, 2 H), 9.17-9.23 (m, 1 H), 12.30-12.48 (m, 1 H).
Example 3210

728
A^c/s-4-(4-Dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-isonicotinaimde
dihydrochloride
Step A: Synthesis of Ar-[ci5-4-(4-dimethyIamino-pyrimidin-2-ylamino)-cyclohexyI]-
isonicotinamide dihydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e 341, M (free) + H+; ]HNMR(300 MHz, DMSO-d6) 8 1.67-1.99 (m, 8 H), 3.16 (s, 3 H),
3.20 (s, 3 H), 3.84-4.07 (m, 2 H), 6.37 (d,J = 7.4 Hz, 1 H), 7.86-8.02 (m, 1 H), 8.25 (d, J= 6.5 Hz,
2 H), 8.48-8.57 (m, 1 H), 8.95-9.13 (m, 3 H), 12.53-12.69 (m, 1 H).
Example 3211
5-Bromo-Ar-lcis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-
nicotinamide hydrochloride
Step A: Synthesis of 5-Bromo-7V-[C1-5-4-(4-dimethylamino-pynmidin-2-ylamino)-
cyclohexylj-nicotinamide hydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e 419, M (free) + H+; ]H NMR (300 MHz, CDC13) 8 1.64-2.07 (m, 8 H), 3.18 (s, 3 H), 3.28
(s, 3 H), 4.04-4.31 (m, 2 H), 5.95-6.04 (m, 1 H), 7.37-7.65 (m, 2 H), 8.42 (brs, 1 H), 8.63-8.74 (m, 1
H), 8.79 (brs, 1 H), 9.12 (brs, 1 H), 12.72-12.97 (m, 1 H).
Example 3212
Ar-[c«-4-(4-Dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-6-trifluoromethyl-
nicotinamide hydrochloride
Step A: Synthesis of 7V-[c«-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-6-

729
trifluoromethyl-nicotinamidehydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e 409, M (free) + H+; 'H NMR (300 MHz, CDCI3) 5 1.63-2.06 (m, 8 H), 3.18 (s, 3 H),3.27
(s, 3 H), 4.07-4.34 (m, 2 H), 5.98 (d, J= 7.4 Hz, I H), 7.47-7.62 (m, 2 H), 7.72 (d, J= 8.0 Hz, 1 H),
8.35-8.45 (m, 1 H), 8.57-8.74 (m, 1 H), 9.24-9.31 (m, 1 H).
Example 3213
4-Chloro-pyridine-2-carboxylic acid [cjy-4-(4-dimethylamino-pyrimidin-2-ylamino)-
cyC1-5hexyl]-amide hydrochloride
Step A: Synthesis of 4-chloro-pyridine-2-carboxyIic acid [c/s-4-(4-dimethylamino-pyrimidin-
2-ylamino)-cyC1-5hexyI]-amide hydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e375, M (free) +Hf;lHNMR(300 MHz, CDC13) 8 1.71-2.09 (m, 8 H), 3.18 (s, 3 H), 3.28
(s, 3 H), 4.01-4.24 (m, 2 H), 5.88-6.08 (m, 1 H), 7.39-7.59 (m, 2 H), 8.05-8.35 (m, 2 H), 8.43-8.72 (m,
2 H), 13.20-13.45 (m, 1 H).
Example 3214
7V-[c«-4-(4-Dimethylamino-pyrimidin-2-ylamino)-cycloliexylJ-4-fluoro-benzamide
hydrochloride
Step A: Synthesis of Ar-[ciy-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-
4-fluoro-benzamide hydrochloride.
Using the procedure for the step D of example 3129, the title compound was obtained.
ESI MS m/e 380, M (free) + Na+; 'H NMR (300 MHz, CDCI3) 5 1.63-2.24 (m, 8 H), 3.17 (s, 3 H),
3.27 (s, 3 H), 4.01-4.32 (m, 2 H), 5.97 (d,/= 7.3 Hz, 1 H), 6.38-6.57 (m, I H), 7.01-7.17 (m, 2 H),

730
7.41-7.54 (m, 1 H), 7.77-7.91 (m, 2 H), 8.76-8.84 (m, 1 H), 12.86-13.14 (m, 1 H).
Example 3215
3-Chloro-Ar-[cw-4-(4-dimethyIamino-pyrimidin-2-ylamino)-cyC1-5hexyl]-5-fluoro-benzamide
hydrochloride
Step A: Synthesis of 3-Chloro-7V-[c/s-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-
5-fIuoro-benzamide hydrochloride.
Using the procedure for the step A of example 3198, the title compound was
obtained.
ESI MS m/e 414, M (free) + Na+; 'H NMR (300 MHz, CDC13) 5 1.64-2.03 (m, 8 H), 3.17 (s, 3 H),
3.28 (s, 3 H), 4.02-4.31 (m, 2 H), 5.97 (d, J= 7.4 Hz, 1 H), 6.53-6.67 (m, 1 H), 7.16-7.23 (m, 1 H),
7.41-7.51 (m, 2 H), 7.58-7.64 (m, 1 H), 8.76-8.91 (m, 1 H).
Example 3216
A'-fc/s^^-Dimethylamino-pyrimidin^-ylaminoycyclohexyll-S^jS-trifluoro-benzamide
hydrochloride
Step A: Synthesis of Ar-[c«-4-(4-dimethyIamino-pyrimidin-2-ylamino)-cyclohexyl]-
3,4,5-trifluoro-benzamide hydrochloride.
Using the procedure for the step A of example 3198, the title compound was
obtained.
ESI MS m/e 416, M (free) + Na+; ]HNMR (300 MHz, CDCi3) 5 1.66-2.03 (m, 8 H), 3.18 (s, 3 H),
3.28 (s, 3 H), 4.01-4.34 (m, 2 H), 5.98 (d, J= 7.4 Hz, 1 H), 6.70-6.79 (m, 1 H), 7.42-7.63 (m, 3 H),
8.73-8.86 (m, 1 H).

731
Example 3217
3,5-Di-tert-butyI-Ar-[C1-5-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyC1-5hexyl]-4-hydroxy-
benzamide hydrochloride
Step A: Synthesis of 3,5-di-tert-butyI-Ar-[c«-4-(4-dimethyIamino-pyrimidin-2-yIamino)-
cyclohexyl]-4-hydroxy-benzamide hydrochloride.
Using the procedure for the step A of example 3198, the title compound was
obtained.
ESI MS m/e 490, M (free) + Na+; 'HNMR (300 MHz, CDC13) 5 1.47 (s, 18 H), 1.63-2.13 (m, 8 H),
3.17 (s, 3 H), 3.28 (s, 3 H), 4.05-4.27 (m, 2 H), 5.52 (s, 1 H), 5.90-6.02 (m, 1 H), 6.57-6.73 (m, 1 H),
7.41-7.55 (m, 1 H), 7.63 (s, 2 H), 8.60-8.77 (m, 1 H), 13.00-13.24 (m, 1 H).
Example 3218
l-(23-Dichloro-phenyl)-3-[m-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-
urea hydrochloride
Step A: Synthesis of l-(23-dichloro-phenyI)-3-[c/s-4-(4-dimethylamino-pyrimidin-2-ylamino)-
cyclohexyl]-urea hydrochloride.
To a solution of 7V2-(c/5-4-amino-cyclohexyl)-A?4//4-dimethyl-pynmidine-2,4-
diamine in step C of example 3129 (300 mg) in DMSO (3 mL) was added
l,2-dich!oro-3-isocyanato-benzene (264 mg). The mixture was stirred at ambient temperature for 12
hr and poured into water. The precipitate was filtrated, washed with water, and purified by
medium-pressure liquid chromatography (NH-silica gel, 25% to 50% EtOAc in hexane). To a
solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (3 0 mL).
The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure.
A suspension of the residue in Et2O (20 mL) was stirred at ambient tempareture for 1 hr. The

732
precipitate was collected by filtration, washed with Et2O, and dried under reduced pressure to give
l~(2,3-dichloro-phenyl)-3-[c/5-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-
urea hydrochloride (421 mg) as a white solid.
ESI MS m/e 445, M (free) +Na+; 'HNMR(200 MHZ, CDC13) 5 1.63-2.19 (m, 8 H), 3.15 (s, 3 H),
3.25 (s, 3 H), 3.80-4.22 (m, 2 H), 5.94 (d, J= 1A Hz, 1 H), 7.00-7.19 (m, 2 H), 7.43-7.64 (m, 2 H),
8.16 (dd, 7=8.3, 1.7 Hz, 1 H), 8.37-8.52 (m, 1 H), 12.70-13.00 (m, 1 H).
Example 3219
Ar-[c/5-4-(4-Dimethylamino-pyrimidin-2-ylamino)-cyclohexylmethyl]-3,4-difluoro-
benzamide hydrochloride
Step A: Synthesis of Ar-[cw-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyc1ohexylmethyll-
3,4-difluoro-benzamide hydrochloride.
To a solution of A^-(cw-4-aminomethyl-cyC1-5hexyl)-A'4^V4-dimethyl-pyrimidine-2,4-
diamine in step B of example 3145 (300 mg) in CHC13 (3 mL) were added iPr2NEt (0.59 mL) and
3,4-difIuoro-benzoyl chloride (233 mg). The mixture was stirred at ambient temperature for 17 hr.
The reaction was quenched with saturated aqueous NaHCO3 and the aqueous layer was extracted with
CHCI3 (three times). The combined organic layer was dried over MgSGt, filtered, concentrated under
reduced pressure, and purified by medium-pressure liquid chromatography (NH-silica gel, 33%
EtOAc in hexane). To a solution of the above material in EtOAc (2 mL) was added 4 M hydrogen
chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated
under reduced pressure. A suspension of the residue in Et3O (20 mL) was stirred at ambient
tempareture for 1 hr. The precipitate was collected by filtration, washed with Et?O, and dried under
reduced pressure to give 7V-[c/5-4-(4-dimethyIamino-pyrimidin-2-ylamino)-cyclohexylmethyl]-
3,4-difluoro-benzamide hydrochloride (155 mg) as a white solid.
ESI MS m/e 412, M (free) + Na+; ]HNMR (200 MHz, CDC13) 5 1.26-2.03 (m, 9 H), 3.16 (s, 3 H),
3.26 (s, 3 H), 3.37-3.61 (m, 2 H), 4.18-4.35 (m, 1 H), 5.94 (d, J= 1A Hz, 1 H), 6.82-7.33 (m, 2 H),

733
7.46 (d, J= 1A Hz, 1 H), 7.74-8.07 (m, 2 H), 8.83-9.12 (m, I H).
Example 3220
Ar-[cw-4-(4-Dimethylamino-pyrimidin-2-ylamino)-cyclohexylmethyl]-2-(2,3,6-trichloro-
phenyl)-acetamide hydrochloride
Step A: Synthesis of A^cw-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexylmethyl]-
2-(2,3)6-trichloro-phenyl)-acetamide hydrochloride.
Using the procedure for the step C of example 3118, the title compound was
obtained.
ESI MS m/e 492, M (free) + Na+; !H NMR (300 MHz, CDCI3) 5 1.57-1.98 (m, 9 H), 3.16 (s, 3 H),
3.21-3.33 (m, 4 H), 4.16 (s, 2 H), 4.20-4.34 (m, 1 H), 5.95-5.99 (m, 1 H), 6.51-6.64 (m, 1 H),
7.23-7.51 (m, 3 H), 8.75-8.83 (m, 1 H), 12.80-12.95 (m, 1 H).
Example 3221
9//-Xanthene-9-carboxyIic acid [cis-4-(4-dimethylamino-pyriimdin-2-yIamino)-
cyclohexylmethyl]-amide hydrochloride
Step A: Synthesis of 9//-xanthene-9-carboxylic acid [C1-5-4-(4-dimethylamino-pyrimidin-
2-ylamino)-cyclohexylmethyl]-amide hydrochloride.
Using the procedure for the step C of example 3118, the title compound was
obtained.
ESI MS m/e 480, M (free) + Na+; !H NMR (300 MHz, CDCI3) 5 1.27-1.94 (m, 9 H), 3.05-3.19 (m,
5 H), 3.24 (s, 3 H), 4.14-4.28 (m, 1 H), 5.10 (s, 1 H), 5.91 (d, 7= 7.4 Hz, 1 H), 6.19-6.33 (m, 1 H),
6.98-7.18 (m, 3 H), 7.20-7.31 (m, 2 H), 7.37-7.54 (m, 3 H), 8.62-8.82 (m, 1 H) 12.88-13.08 (m, 1 H).

734
Example 3222
l-(2,3-Dichloro-phenyl)-3-[c/5-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexylmethyl]-
urea hydrochloride
Step A: Synthesis of l-(2,3-dichloro-phenyl)-3-[c/y-4-(4-dimethylamino-pyrimidin-2-ylainino)-
cydohexylmethyl]-urea hydrochloride.
To a solution of Ar2-(c/^-4-aminomethyl-cyclohexyI)-7V4,A/4-dimethyl-
pyrimidine-2,4-diamine in step B of example 3145 (300 mg) in DMSO (3 mL) was added
1,2-dichloro-3-isocyanato-benzene (249 mg). The mixture was stirred at ambient temperature for 15
hr and poured into water (20 mL). The precipitate was filtrated, washed with water, and purified by
medium-pressure liquid chromatography (NH-silica gel, 25% to 50% EtOAc in hexane). To a
solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL).
The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure.
A suspension of the residue in Et2O (20 mL) was stirred at ambient tempareture for 1 hr. The
precipitate was collected by filtration, washed with Et2O, and dried under reduced pressure to
l-(2,3-dichloro-phenyl)-3-[c/5-4-(4-dimethylamino-pyrimidin-2'ylamino)-cyclohexylmethyl]-
urea hydrochloride (260 mg) as a white solid.
ESI MS m/e 437, M+; 'HNMR (200 MHz, CDCI3) 6 1.35-2.10 (m, 9 H), 3.16 (s, 3 H), 3.26 (s, 3 H),
3.32-3.47 (m, 2 H), 4.27-4.47 (m, I H), 5.96 (d, J= 7.5 Hz, 1 H), 6.80-7.20 (m, 3 H), 7.47 (d, J= 7.5
Hz, 1 H), 8.08-8.37 (m, 2 H), 8.63-8.93 (m, 1 H).
Example 3223
3,4-Difluoro-Af-[c/s-4-(4-methyIamino-pyrimidin-2-ylamino)-cyclohexyl]-benzamide-
hydrochloride
Step A: Synthesis of (2-ch lo ro-py rim id in-4-yl)-m ethyl-am in e.

735
To a solution of 2,4-dichloro-pyrimidine (15.0 g) in THF (150 mL) was added 40% aqueous
MeNH2 (19.5 g). The mixture was stirred at ambient temperature for 1.5 hr. The solution was poured
into saturated aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (three times). The
combined organic layer was dried over MgSO4, filtrated, concentrated, and purified by flash
chromatography (NH-silica, 20% EtOAc in hexane) to give (2-chloro-pyrimidin-4-yl)-methyl-amine
(10.0 g) as a white solid and (4-chloro-pyrimidin-2-yl)-methyl-amine (0.87 g, 6%) as a white solid.
(2-chloro-pyrimidin-4-yl)-methyl-amine;
ESIMSm/el43, M ; 'H NMR (300 MHz, CDC13) 6 3.01 (d, J = 5.0 Hz, 3 H), 5-58-5.96 (m, 1 H),
6.55(d,J=5.1Hz, 1 H), 8.09-8.23 (m, 1 H).
(4-chloro-pyrimidin-2-yl)-methyl-amine;
ESI MS m/e 143, M+; lH NMR (300 MHz, CDC13) 8 2.98 (d, J= 5.0 Hz, 3 H), 6.27 (d, J= 6.1 Hz,
1 H), 7.93-8.20 (m, 1 H).
Step B: Synthesis of [cis-4-(4-methyIamino-pyrimidin-2-ylaniino)-cyC1-5hexyI]-
carbamic acid tert-butyl ester.
A mixture of (2-chloro-pyrimidin-4-yl)-methyl-amine (2.50 g) and (cjs-4-amino-
cyclohexyl)-carbamic acid tert-buXy\ ester obtained in step B of example 1 (4.10 g) in BuOH (2.50
mL) was stirred at reflux for 24 hr. The reaction mixture was poured into saturated aqueous NaHCO3,
and the aqueous layer was extracted with CHCI3 (three times). The combined organic layer was dried
over MgSO4, filtrated, concentrated under reduced pressure, and purified by medium-pressure liquid
chromatography (NH-silica, 25% to 66% EtOAc in hexane) to give [c/5-4-(4-methylamino-pyrimidin-
2-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester (2.63 g) as a white solid.
ESI MS m/e 344, M + Na+; *HNMR (300 MHz, CDC13) 5 1.36-1.88 (m, 17 H), 2.89 (d, J= 5.1 Hz,
3 H), 3.53-3.69 (m, 1 H), 3.84-4.04 (m, 1 H), 4.44-4.70 (m, 2 H), 4.76-4.86 (m, 1 H), 5.69-5.72 (m,
= 1 H), 7.80-7.91 (m, 1 H).
Step C: Synthesis of A^ciM-amino-cyclohexylJ-A^-methyl-pyrimidine^^-diamine.
A solution of [as-4-(4-methyIamino-pyrimidin-2-yIamino)-cyclohexyl]-carbamic acid

736
tert-butyl ester (4.76 g) in EtOAc (48 mL) was cooled on an ice-bath and 4 M hydrogen chloride in
EtOAc (24 mL) was added. The mixture was stirred at ambient temperature for 4 hr and concentrated
under reduced pressure. The residue was dissolved in 1 M aqueous NaOH and the aqueous layer was
extracted with CHC13 (five times). The combined organic layer was dried over MgSO4, filtered,
concentrated under reduced pressure, and dried under reduced pressure to give A^-(c/s-4-amino-
cyclohexyl)-7V4-methyl-pyrimidine-2,4-diamine (3.00 g, 80%) as a white solid.
ESI MS m/e 222, M + KT; 'H NMR (300 MHz, CDCI3) 5 0.95-1.92 (m, 10 H), 2.78-2.99 (m, 4 H),
3.92-4.08 (m, 1 H), 4.56-4.75 (m, 1 H), 4.84-4.97 (m, 1 H), 5.68 (d, J= 5.9 Hz, 1 H), 7.85 (d, J = 5.7
Hz, 1 H).
Step D: Synthesis of 3,4-difluoro-Ar-[cw-4-(4-methylamino-pyrimidin-2-ylamino)-
cyclohexyl]-benzamidehydrochloride.
To a solution of 3,4-drfluoro-benzoic acid (196 mg) andA^-(c/5-4-amino-cyclohexyl)-
V-methyl-pyrimidine-2,4-diamine (250 mg) in DMF (4 mL) were added Et3N (0.38 mL), HOBt-H2O
(259 mg), and EDC-HC1 (238 mg). The reaction mixture was stirred at ambient temperature for 12
hr. To the mixture was added water (20 mL) and the aqueous layer was extracted with CHC13 (three
times). The combined organic layer was dried over MgSO4, filtered, concentrated under reduced
pressure, and purified by medium-pressure liquid chromatography (NH-silica gel, 33% to 75% EtOAc
in hexane). To a solution of the above material in EtOAc (10 mL) was added 4 M hydrogen chloride
in EtOAc (0.2 mL). The mixture was stirred at ambient temperature for I hr. The precipitate was
collected by filtration, washed with EtOAc, and dried under reduced pressure to give
3,4-difluoro-A^-[c/5-4-(4-methylamino-pyrimidin-2-ylamino)-cyclohexyi]-
benzamide hydrochloride (317 mg) as a white solid.
ESI MS m/e 362, M (free) + \t; !H NMR (300 MHz, DMSO-d6) 5 1.59-1.90 (m, 8 H), 2.89 (d, J =
4.6 Hz, 3 H), 3.80-4.11 (m, 2 H), 6.03-6.13 (m, 1 H), 7.47-8.03 (m, 4 H), 8.27-8.49 (m, 2 H),
8.82-9.06 (m, 1 H), 11.92-12.11 (m, 1 H).

737
Example 3224
3-Chloro-4-fluoro-Ar-[C1-5-4-(4-methylamino-pyrimidin-2-ylainino)-cyclohexyl]-
benzamide hydrochloride
Step A: Synthesis of 3-chloro-4-fluoro-Ar-[C1-5-4-(4-methylamino-pyrimidin-2-ylamino)-
cyclohexylj-benzamide hydrochloride.
Using the procedure for the step C of example 3223, the title compound was
obtained.
ESI MS m/e 378, M (free) + H+; *H NMR (300 MHz, DMSO-d6) 5 1.59-1.90 (m, 8 H), 2.89 (d, J =
4.6 Hz, 3 H), 3.77-4.10 (m, 2 H), 6.00-6.12 (m, 1 H), 7.49-7.60 (m, 1 H), 7.67-7.76 (m, 1 H),
7.85-7.94 (m, 1 H), 8.U (dd, J= 7.1, 2.2 Hz, 1 H), 8.24-8.51 (m, 2 H), 8.82-8.94 (m, 1 H),
11.80-11.98 (m, 1H).
Example 3225
Ar-[c/s-4-(4-Ethylamino-pyrimidin-2-ylamino)-cyclohexyl]-3,4-difluoro-benzamide
hydrochloride
Step A: Synthesis of (2-chloro-pyrimidin-4-yI)-ethyl-amine.
To the solution of 2,4-dichloro-pyrimidine (5.00 g) in THF (50 mL) was added 70% aqueous
EtNH2 (5.40 g). The mixture was stirred at ambient temperature for 1 hr. To the residue was added
saturated aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (two times). The
combined organic layer was dried over MgSO4, filtered, concentrated under reduced pressure, and
purified flash chromatography (silica gel, 17% to 50% EtOAc in hexane) to give
(2-chioro-pyrimidin-4-yl)-ethyI-amine (3.69 g) as a white solid and (4-chloro-pyrimidin-2-yl)-
ethyl-amine (1.28 g) as a white solid.
(2-ch loro-pyr im i d in-4-y l)-ethy 1-am ine;
ESI MS m/e 157, M+; 'H NMR (500 MHz, CDC13) 5 1.26 (t, J= 7.3 Hz, 3 H), 3.16-3.62 (m, 2 H),

738
4.80-5.95 (m, 1 H), 6.23 (d, J = 5.8 Hz, 1 H), 8.02-8.22 (m, 1 H).
(4-chloro-pyrimidin-2-yl)-ethyl-amine;
CI MS m/e 158, M + H+; !H NMR (500 MHz, CDC13) 5 1.23 (t, J= 7.5 Hz, 3 H), 3.42-3.49 (m, 2 H),
5.30-5.62 (m, 1 H), 6.54 {d,J= 5.2 Hz, 1 H), 8.02-8.22 (m, 1 H).
Step B: Synthesis of Ar-[c/s-4-(4-ethylamino-pyrimidin-2-ylamino)-cyclohexyl]-
3,4-difluoro-benzamide hydrochloride.
To a solution of JV-(cw-4-amino-cyclohexyI)-3,4-difluoro-benzamide obtained in step D of
example 3031 (300 mg) in BuOH (1 mL) was added (2-chIoro-pyrimidin-4-yI)-
ethyl-amine (532 mg). The mixture was heated in a microwave synthesizer at 200°C for 30 min. To
the mixture was added saturated aqueous NaHCO3 and the aqueous layer was extracted with CHC13
(three times). The combined organic layer was dried over MgSO4, filtrated, concentrated under
reduced pressure, and purified by medium-pressure liquid chromatography (NH-silica gel, 20% to
50% in EtOAc in nexane). To a solution of the above material in EtOAc (10.0 mL) was added 4 M
hydrogen chloride in EtOAc (5.00 mL). The mixture was stirred at ambient temperature for 1 hr and
concentrated under reduced pressure. A suspension of the above material in Et2O (20 mL) was stirred
at ambient tempareture for 4 hr. The precipitate was collected by filtration, washed with Et^O, and
dried under reduced pressure to give A^-[c/5-4-(4-ethylamino-pyrimidin-2-ylamino)-cyclohexyl]-
3,4-difluoro-benzamide hydrochloride (398 mg) as a white solid.
ESI MS m/e 398, M (free) + Na+; !H NMR (500 MHz, CDCI3) 5 1.19-1.42 (m, 3 H), 1.61-2.05 (m,
8 H), 3.46-3.65 (m, 2 H), 4.00-4.34 (m, 2 H), 5.85-6.00 (m, 1 H), 6.42-6.72 (m, 2 H), 7.11-7.37 (m,
2 H), 7.52-7.82 (m, 2 H), 8.68-8.90 (m, 1 H).
Example 3226
Ar-{c/y-4-[4-(Ethyl-methyl-amino)-pyrimidin-2-ylamino]-cyclohexyI}-3,4-difluoro-
benzamide hydrochloride

739
Step A: Synthesis of (2-chloro-pyrimidin-4-yl)-ethyl-methyl-amine.
To the solution of 2,4-dichloro-pyrimidine (5.00 g) in THF (50 mL) was added
ethyl-methyl-amine (2.08 g). The mixture was stirred at ambient temperature for 1 hr. To the residue
was added saturated aqueous NaHCO3 and the aqueous layer was extracted with CHCI3 (two times).
The combined organic layer was dried over MgSO4, filtered, concentrated under reduced pressure,
and purified flash chromatography (silica gel, 17% to 50% EtOAc in hexane) to give
(2-chloro-pyrimidin-4-yl)-ethyl-methyl-amine (4.49 g) as a white solid and (4-chloro-pyrimidin-2-yl)-
ethyl-methyl-amine (0.91 g) as a colorless oil.
(2-chloro-pyrimidin^-yI)-ethyl-methyI-amine;
CT MS m/e 172, M (free) + H+; ]H NMR (500 MHz, CDCI3) 8 1.18 (t, J = 3.0 Hz, 3 H), 3.06 (brs, 3
H), 3.35-3.70 (m, 2 H), 6.29 (d, J= 4.8 Hz, 1 H), 7.99(d, J = 6.1 Hz, 1 H).
(4-chloro-pyrimidin-2-yl)-ethyl-methyl-amine;
CI MS m/e 172, M + it; !H NMR (500 MHz, CDC13) 5 1.17 (t, J= 3.0 Hz, 3 H), 3.10 (s, 3 H), 3.66
(q, J= 7.0 Hz, 2 H), 6.45 (d, .7=5.0 Hz, 1 H), 8.14 (d, J= 5.0 Hz, 1 H).
Step B: Synthesis of JV-{c/s-4-[4-(ethyl-methyl-amino)-pyrimidin-2-ylamino]-
cyclohexyI}-3,4-difluoro-benzamide hydrochloride.
Using the procedure for the step B of example 3225, the title compound was
obtained.
ESI MS m/e 412, M (free) + Na+; !H NMR (300 MHz, CDCI3) 8 1.18-1.33 (m, 3 H), 1.64-2.03 (m,
8 H), 3.13-3.32 (m, 3 H), 3.44-3.56 (m, 1 H), 3.67-3.82 (m, 1 H), 4.04-4.31 (m, 2 H), 5.90-6.00 (m,
1 H), 6.59-6.72 (m, 1 H), 7.14-7.27 (m, 1 H), 7.43-7.62 (m, 2 H), 7.68-7.79 (m, 1 H), 8.71-8.83 (m,
1H).
Example 3227
3,4-Difluoro-Ar-(m-4-{4-{(2-hydroxy-ethyl)-methyl-amino]-pyrimidin-2-ylamino}-

740
cyclohexyl)-benzamide hydrochloride
Step A: Synthesis of [(2-chloro-pyrimidin-4-yl)-methyI-amino]-ethanoI.
To the solution of 2,4-dichIoro-pyrimidine (5.00 g) in THF (50 mL) was added
2-methylamino-ethanol (2.65 g). The mixture was stirred at ambient temperature for Ihr. To the
residue was added saturated aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (two
times). The combined organic layer was dried over MgSO4, filtered, concentrated under reduced
pressure, and purified flash chromatography (silica gel, 17% to 50% EtOAc in hexane) to give
[(2-chloro-pyrimidin-4-y!)-methyl-amino]-ethanol (3.50 g) as a white solid and [(4-chloro-
pyrimidin-2-yl)-methyl-amino]-ethanol (827 mg) as a white solid.
[(2-chloro-pyrimidin-4-yl)-methyl-amino]-ethanol;
ESI MS m/e 188, M (free) + H+; ]H NMR (500 MHz, CDC13) 8 2.91 (brs, 3 H), 3.13 (s, 3 H),
3.64-3.92 (m, 4 H), 6.46-6.49 (m, 1 H), 7.99 (d, J = 6.1 Hz, 1 H).
[(4-chloro-pyrimidin-2-yl)-methyI-amino]-ethanoI
ESI MS m/e 210, M + Na+; ]H NMR (500 MHz, CDC13) 5 3.23 (s, 3 H), 3.76-3.92 (m, 4 H),
6.52 (d, y = 5.2 Hz, 1 H), 8.12 (d, J= 4.6 Hz, 1 H).
Step B: Synthesis of 3,4-difluoro-Ar-(c/y-4-{4-[(2-hydroxy-ethyl)-methyl-amino]-
pyrimidin-2-ylamino}-eyclohexyl)-benzamide hydrochloride.
Using the procedure for the step B of example 3225, the title compound was
obtained.
ESI MS m/e 428, M (free)+ Na+;iHNMR (300 MHz, DMSO-d6) 5 1.61-1.98 (m, 8 H), 3.13-3.25 (m,
3 H), 3.54-4.31 (m, 5 H), 4.76-5.02 (m, 1 H), 6.26-6.52 (m, 1 H), 7.48-7.62 (m, 1 H), 7.68-8.17 (m,
4 H), 8.28-8.47 (m, 1 H), 11.74-11.95 (m, 1 H).
Example 3228
3-ChIoro-Ar-[C1-5-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-4-fluoro-

741
benzamide hydrochloride
Step A: Synthesis of 7V-(c/s-4-amino-cyclohexyl)-3-chloro-4-fluoro-benzamide.
To a solution of 3-chloro-4-fluoro-benzoic acid (26.9 g) and (c/s-4-amino-
cyclohexyl)-carbamic acid ferf-butyl ester (30.0 g) in DMF (300 mL) were added Et3N (46.8 mL),
HOBt-H2O (32.2 g), and EDC-HC1 (29.5 g). The reaction mixture was stirred at ambient temperature
for 20 hr. To the mixture was added water (1.20 L) and the aqueous layer was extracted with CHCI3
(three times). The combined organic layer was dried over MgSO4, filtered, and concentrated under
reduced pressure. A solution of the above material in EtOAc (650 mL) was cooled on an ice-bath and
4 M hydrogen chloride in EtOAc (325 mL) was added. The mixture was stirred at ambient
temperature for 16 hr and concentrated under reduced pressure. The residue was dissolved in 1 M
aqueous NaOH (300 mL) and the aqueous layer was extracted with CHCI3 (three time). The
combined organic layer was dried over MgSO4, filtered, concentrated under reduced pressure, and
dried under reduced pressure to give A^-(cw-4-amino-cyclohexyl)-3-chloro-4-fluoro-benzamide (44.4
g) as a brown solid.
ESI MS m/e 271, M (free) + it; ]H NMR (300 MHz, CDC13) 8 1.37-1.92 (m, 8 H), 2.94-3.08 (m, 1
H), 4.06-4.22 (m, 1 H), 6.13-6.31 (m, 1 H), 7.19 (t, J=8.5 Hz, 1 H), 7.61-7.70 (m, 1 H), 7.79-7.87 (m,
1H).
Step B: Synthesis of 3-chloro-Af-[c/s-4-(4-dimethyJamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexyl]-4-fluoro-benzamide hydrochloride.
To a solution of A/-(c/5-4-amino-cyclohexyl)-3-chloro-4-iluoro-benzamide (432 mg) in BuOH
(1 mL) was added 2-chloro-4-dimethyIamino-5-methylpyrimidine obtained in step A of example 3119
(250 mg). The mixture was heated in a microwave synthesizer at 200°C for 10 min. To the mixture
was added saturated aqueous NaHCO3 and the aqueous layer was extracted with CHCI3 (three times).
The combined organic layer was dried over MgSO4, filtrated, concentrated under reduced pressure,
and purified by medium-pressure liquid chromatography (NH-silica gel, 20% to 50% EtOAc in
hexane) to give a pale yellow oil. To a solution of the above material in EtOAc (10 mL) was added

742
4 M hydrogen chloride in EtOAc (0.2 mL). The mixture was stirred at ambient temperature for 1 hr
and concentrated under reduced pressure. A suspension of the above material in Et2O (20 mL) was
stirred at ambient tempareture for 4 hr. The precipitate was collected by filtration, washed with Et2O,
and dried under reduced pressure to give 3-chIoro-/vr-[cw-4-(4-dimethy]amino-5-methyl-pyrimidin-
2-ylamino)-cyC1-5hexyi]-4-fIuoro-benzamide hydrochloride (174 mg) as a white solid.
ESI MS m/e 406, M (free) + H+; 'HNMR (300 MHz, CDC13) 5 1.61-2.02 (m, 8 H), 2.25 (s, 3 H), 3.30
(s, 6 H), 4.02-4.26 (m, 2 H), 6.81-6.93 (m, 1 H), 7.13-7.27 (m, 2 H), 7.70-7.78 (m, 1 H), 7.93-8.00 (m,
1 H), 8.50-8.63 (m, 1 H), 12.68-12.85 (m, 1 H).
Example 3229
3-Chloro-Ar-[c«-4-(4-dimethylamino-5-fluoro-pyriinidin-2-ylamino)-cyc]ohexyl]-4-fluoro-
benzamide hydrochloride
Step A: Synthesis of 3-chloro-A^c/s-4-(4-dimethylamino-5-fluoro-pyrimidin-2-ylamino)-
cyclohexyl]-4-fluoro-benzamide hydrochloride.
Using the procedure for the step B of example 3228, the title compound was
obtained.
ESI MS m/e 410, M (free) + H+; 'H NMR (300 MHz, CDC13) 5 1.64-2.03 (m, 8 H), 3.36 (s, 6 H),
4.00-4.23 (m, 2 H), 6.73-6.84 (m, I H), 7.18 (t,J= 8.6 Hz, 1 H), 7.45 (d, J= 7.6 Hz, 1 H), 7.67-7.76
(m, 1 H), 7.95 (dd, J= 7.0, 2.2 Hz, 1 H), 8.64-8.78 (m, 1 H).
Example 3230
3-C hloro-iV- [cis-4-(4-d i m ethyla m in o-6-m ethy l-py ri m id i n-2 -y lam ino)-cyclohexyl] -4-fl u o ro-
benzamide hydrochloride
Step A: Synthesis of 3-chIoro-iV-[c«-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-

743
cyclohexyl]-4-fluoro-benzamide hydrochloride.
Using the procedure for the step B of example 3228, the title compound was
obtained.
ESI MS m/e 406, M (free) + H+; lH NMR (300 MHz, CDC13) 8 1.62-2.04 (m, 8 H), 2.36 (s, 3 H), 3.15
(s, 3 H), 3.27 (s, 3 H), 4.01-4.31 (m, 2 H), 5.76 (s, 1 H), 6.73-6.84 (m, 1 H), 7.19 (t, J= 8.6 Hz, 1 H),
7.68-7.79 (m, I H), 7.97 (dd, J= 6.9, 2.2 Hz, 1 H), 8.50-8.63 (m, 1 H), 12.94-13.16 (m, 1 H).
Example 3231
Ar-[C1-5-4-(4-Dimethylamino-6-ethyl-pyrimidin-2-ylaniino)-cyclohexyl]-3,4-difluoro-
benzamide hydrochloride
Step A: Synthesis of (2,6-Dichloro-pyrimidin-4-yl)-dimethyl-amine.
To the solution of 2,4,6-trichloro-pyrimidine (10.0 g) in THF (50 mL) were added 50%
aqueous Me?NH (4.92 g) and iPr2NEt (8.46 g). The mixture was stirred at ambient temperature for
1.5 hr and concentrated under reduced pressure. To the residue was added saturated aqueous
NaHCOs and the aqueous layer was extracted with CHCI3 (three times). The combined organic layer
was dried over MgSO4, filtered, concentrated under reduced pressure, and purified flash
chromatography (NH-silica gel, 3% EtOAc in hexane) to give
(2,6-dichIoro-pyrimidin-4-yI)-dimethyl-amine (6.03 g) as white solid.
ESI MS m/e 192, M+; *H NMR (300 MHz, CDC13) 8 2.77-3.46 (m, 6 H), 6.34 (s, 1 H).
Step B: Synthesis of (2-chloro-6-ethyl-pyrimidin-4-yl)-dimethyl-amine.
A solution of ZnBr2 (3.87 g) in THF (60 mL) was cooled to -60°C and 1 M EtMgBr in THF
(17.2 mL) was added. The mixture was stirred at-60°C for 1 hr and wanned to ambient temperature.
To the mixture was added (2,6-dichloro-pyrimidin-4-yl)-dimethyl-amine in THF (60 mL) and stirred
at reflux for 5 days. To the mixture was added saturated aqueous NH4CI and the aqueous layer was
extracted with CHC13 (three times). The combined organic layer was dried over MgSO4, filtered,

744
concentrated under reduced pressure, and purified by medium-pressure liquid chromatography (silica
gel, 17% to 33% EtOAc in hexane) to give (2-chloro-6-ethyl-pyrimidin-4-yl)-dimethyl-amine (352
mg) as pale yellow solid and (6-chloro-2-ethyl-pyrimidin-4-yl)-dimethyl-amine (622 mg) as pale
yellow solid.
(2-chloro-6-ethyl-pyrimidin-4-yI)-dimethyI-amine;
ESI MS m/e 208, M (free) + Na+; *H NMR (300 MHz, CDC13) 6 1.25 (t, J = 1.6 Hz, 3 H), 2.54-2.66
(m,2H), 3.11 (s,6H),6.15(s, 1 H).
(6-chIoro-2-ethyl-pyrimidin-4-yl)-dimethyl-amine;
ESI MS m/e 186, M + H+; 'H NMR (300 MHz, CDCI3) 5 1.29 (t, J= 7.6 Hz, 3 H), 2.74 (q, J= 7.7
Hz, 2 H), 3.10 (s, 6 H), 6.24 (s, 1 H).
StepC: Synthesis of 7V-[c/s-4-(4-dimethylamino-6-ethyl-pyrimidin-2-ylamino)-cyclohexyI]-3,4-
diiluoro-benzamide hydrochloride
Using the procedure for the step B of example 3225, the title compound was
obtained.
ESI MS m/e 426, M (free) + Na+; lHNMR (300 MHz, CDC13) 5 1.29-1.44 (m, 3 H), 1.58-2.19 (m,
8 H), 2.54-2.77 (m, 2 H), 3.15 (s, 3 H), 3.26 (s, 3 H), 3.98-4.34 (m, 2 H), 5.74 (s, 1 H), 6.41-6.63 (m,
1 H), 7.08-7.32 (m, 1 H), 7.46-7.81 (m, 2 H), 8.58-8.81 (m, 1 H), 12.83-13.09 (m, 1 H).
Example 3232
Ar-[c«'-4-(4,6-Bis-diniethylamino-pyrimidiii-2-ylamino)-cyC1-5hexyl]-3,4-difluoro-benzamide
hydrochloride
Step A: Synthesis of 2-chloro-7V^V^V,/V-tetramethyl-pyrimidine-4,6-diamine.
To the solution of (2,6-dichIoro-pyrimidin-4-yl)-dimethyI-amine obtained in step A of
example 3231 (1.60 g) in THF (2 rnL) was added 50% aqueous Me2NH (789 mg). The mixture was
stirred at reflux for 3.5 hr in a sealed tube. To the residue was added saturated aqueous NaHCO3 and

745
the aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over
MgSO4, filtered, concentrated under reduced pressure, and purified by medium-pressure liquid
chromatography (silica gel, 20% EtOAc in hexane) to give 2-chIoro-AyvyV',JVT-tetramethyI-
pyrimidine-4,6-diamine (203 mg) as a pale brown solid and 6-chioro-JV,iV,./V,/V-tetramethyl-
pyrimidine-2,4-diamine (1.43 g) as a pale yellow solid.
2-chloro-Ar,A^,7V^V-tetramethyI-pyrimidine-4,6-diamine;
ESI MS m/e 201, M (free) + H+; 'H NMR (300 MHz, CDC13) 5 3.05 (s, 12 H), 5.15 (s, 1 H).
6-chloro-jV,Ar,A^,7V-tetramethyl-pyrimidine-2,4-diamine;
ESI MS m/e 201, M + H+; ]HNMR (300 MHz, CDC13) 5 3.04 (s, 6 H), 3.13 (s, 6 H), 5.76 (s, 1 H).
Step B: Synthesis of A^cw-4-(4,6-bis-dimethylamino-pyrimidin-2-yIamino)-
cyclohexyl]-3,4-difluoro-benzamidehydrochloride.
Using the procedure for the step B of example 3225, the title compound was
obtained.
ESI MS m/e 441, M (free) + Na+; 'HNMR (300 MHz, CDC13) 5 1.61-2.09 (m, 8 H), 2.96-3.38 (m,
12 H), 4.00-4.31 (m, 2 H), 4.73 (s, I H), 6.65-6.82 (m, 1 H), 7.13-7.25 (m, 1 H), 7.55-7.63 (m, 1 H),
7.68-7.78 (m, 1 H), 8.70-8.82 (m, 1 H), 11.79-11.99 (m, 1 H).
Example 3233
7V-[cw-4-(6-Chloro-4-dimethylamino-pyriinidin-2-ylamino)-cyclohexyIJ-2-phenoxy-
nicotinamide hydrochloride
Step A: Synthesis of iV-[c«-4-(6-chIoro-4-dimethylamino-pyriinidin-2-
ylamino)-cyclohexyl]-2-phenoxy-nicotinamide hydrochloride.
Using the procedure for the step B of example 3 032, the title compound was
obtained.
ESI MS m/e 489, M (free) + Na+; 'H NMR (300 MHz, CDC13) 6 1.52-2.10 (m, 8 H), 2.96-3.38 (m,

746
6 H), 4.02-4.29 (m, 2 H), 5.82-6.03 (m, 1 H), 7.04-7.55 (m, 6 H), 7.80-8.01 (m, 1 H), 8.15-8.28 (m,
1H), 8.47-8.61 (m, I H).
Example 3234
Ar-[C1-5-4-(6-Chloro-4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-3,4-difIuoro-
benzamide hydrochloride
Step A: Synthesis of Af-[c/s-4-(6-chloro-4-dimethylamino-pyrimidin-2-ylamino)-cyC1-5hexyl]-
3,4-difluoro-benzamide hydrochloride.
Using the procedure for the step B of example 3225, the title compound was
obtained.
ESI MS m/e 432, M (free) + Na+; !H NMR (300 MHz, CDCI3) 5 1.63-2.05 (m, 8 H), 3.04-3.37 (m,
6 H), 4.02-4.37 (m, 2 H), 5.88-6.03 (m, 1 H), 6.56-6.86 (m, 1 H), 7.14-7.27 (m, 1 H), 7.51-7.63 (m,
1 H), 7.66-7.82 (m, 1 H), 8.85-9.02 (m, 1 H).
Example 3235
7V-[ci5-4-(4-Amino-quinolin-2-ylamino)-cyclohexylJ-3,4-difluoro-benzamide hydrochloride
Step A: Synthesis of 2-chloro-quinolin-4-ylamine.
To the solution of 2,4-dichIoro-quinoline obtained in step A of example 1 (4.00 g) in IPA (40
mL) was added 28% aqueous NH3 (40.0 mL). The mixture was stirred at reflux for 10 days in a sealed
tube. To the residue was added saturated aqueous NaHCO3 and the aqueous layer was extracted with
CHCb (three times). The combined organic layer was dried over MgSC>4, filtered, concentrated under
reduced pressure, and purified by medium-pressure liquid chromatography (silica gel, 9% to 17%
EtOAc in hexane) to give 2-chloro-quinoIin-4-ylamine (1.39 g) as a white solid and 4-chloro-quinoiin-
2-ylamine (1.17 g) as a white solid.

747
2-chloro-quinolin-4-ylamine;
ESI MS m/e 178, MVHNMR (200 MHz, CDCl3) 5 4.69-4.97 (m, 2 H), 6.61 (s, I H), 7.37-7.78 (m,
3 H), 7.84-8.02 (m, 1 H).
4-chloro-quinolin-2-ylamine
ESI MS m/e 178, M+; !HNMR (300 MHz, CDCl3) 5 4.58-4.96 (m, 2 H), 6.85 (s, 1 H), 7.23-7.41 (m,
1 H), 7.53-7.72 (m, 2 H), 7.98-8.09 (m5 1 H).
Step B: Synthesis of Ar-[c/y-4-(4-amino-quinolin-2-ylamino)-cyclohexyl]-3,4-difluoro-
benzamide hydrochloride.
Using the procedure for the step B of example 3225, the title compound was
obtained.
ESI MS m/e 397, M (free) + H+; ]H NMR (300 MHz, CDC13) 5 1.29-2.15 (m, 8 H), 3.75-3.90 (m, 1
H) 4.05,4.26 (m, 1 H), 5.44-5.59 (m, 2 H), 5.89 (s, 1 H), 6.99-7.43 (m, 3 H), 7.55-7.84 (m, 5 H),
8.81-8.98 (m, 1 H).
Example 3236
2-(C1-5-4-{[l-(3,4-Difluoro-phenyl)-methanoyI]-amino}-cyclohexylamino)-quinoline-
4-carboxyIic acid amide
Step A: Synthesis of 2-chloro-quinoline-4-carboxylic acid amide.
To a solution of 2-chIoro-quinoline-4-carboxylic acid (3.00 g) in DMF (30 mL) were added
28% aqueous NH3 (1.05 g), Et3N (5.04 mL), HOBt-H2O (3.32 g), and EDC-HC1 (3.32 g). The
reaction mixture was stirred at ambient temperature for 16 hr. To the reaction mixture was added
water (20 mL) and the aqueous layer extracted with CHC13 (three times). The combined organic layer
was dried over MgSO4, filtered, concentrated under reduced pressure, purified by medium-pressure
liquid chromatography (NH-silica gel, 20% to 50% EtOAc in hexane) to give 2-chloro-quinoline-
4-carboxylic acid amide (1.77 g) as a white solid.

748
ESI MS m/e 207, M (free) + H+; 'H NMR (300 MHz, DMSO-d6) 8 7.65 (s, 1 H), 7.68-7.77 (m, 1 H),
7.83-7.93 (m, I H), 7.98-8.09 (m, 2 H), 8.18-8.25 (m, 1 H), 8.30-8.40 (m, 1 H).
Step B: Synthesis of 2-(m-4-{[l-(3,4-difluoro-phenyl)-methanoyl]-aminoJ~cyclohexylamino)-
quinoline-4-carboxylic acid amide.
A mixture of 2-chloro-quinoIine-4-carboxylic acid amide (300 mg) and N-(cis-4-amino-
cyclohexyl)-3,4-difluoro-benzamide obtained in step A of example 3031 (406 mg) in butanol (1 mL)
and DMSO (1 mL) was stirred at reflux for 24 hr. The reaction mixture was poured into saturated
aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (three times). The combined
organic layer was dried over MgSO4, filtered, concentrated under reduced pressure, purified by
medium-pressure liquid chromatography (NH-silica gel, EtOAc), and concentrated under reduced
pressure. The above material was washed with and dried under reduced pressure to give
2-(c/5-4-{[l-(3,4-difluoro-phenyl)-methanoyl]-amino}-cyclohexylamino)-quinoline-4-
carboxylic acid amide (136 mg) as a white solid.
ESI MS m/e 447, M (free) + Na+; !H NMR (300 MHz, DMSO-d6) 5 1.61-2.03 (m, 8 H), 3.78-3.93 (m,
1 H), 4.05-4.20 (m, 1 H), 6.89 (s, 1 H), 6.99-7.07 (m, 1 H), 7.11-7.21 (m, 1 H), 7.42-7.61 (m,3H),
7.65-7.82 (m, 3 H), 7.88-7.99 (m, 1 H), 8.02-8.10 (m, 1 H), 8.28-8.36 (m, 1 H).
Example 3237
3,4-Difluoro-Ar-[c«-4-(4-trifluoromethyl-quinolin-2-yI)-amino-cyC1-5hexyI]-benzamide
hydrochloride
Step A: Synthesis of 3,4-difluoro-Af-[c/s-4-(4-trifluoromethyI-quinolin-2-yl)-amino-cyC1-5hexyl]-
benzamide hydrochloride.
Using the procedure for the step B of example 3225, the title compound was
obtained.
ESI MS m/e 472, M (free) + Na+'; !H NMR (300 MHz, CDC13) 5 1.80-2.10 (m, 8 H), 3.99-4.28 (m,

749
2 H), 6.46-6.63 (m, 1 H), 7.12-7.34 (m, 2 H), 7.48-7.63 (m, 2 H), 7.66-7.90 (m, 3 H), 7.94-8.05 (m,
1 H), 10.14-10.35 (m, 1 H).
Example 3238
3,4-Difluoro-A^-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzainide
methanesulfonic acid
Step A: Synthesis of 3,4-difluoro-Ar-[cw-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-
benzamide methanesulfonic acid.
To a solution of jV-(ci5-4-methyl-quinolin-2-yl)-cyclohexane-l,4-diamine obtained in step A of
example 3070 (3.00 g) in CHC13 (30 mL) were added Et3N (3.40 mL) and 3,4-difluoro-benzoyl
chloride (2.28 g). The mixture was stirred at ambient temperature for 6 hr. To the mixture was added
saturated aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (three times). The
combined organic layer was dried over MgSO4, filtered, concentrated under reduced pressure, and
purified by medium-pressure liquid chromatography (NH-silica gel, 20% to 33% EtOAc in hexane
and silica gel, 2% to 5% MeOH in CHC13) to give 3,4-difluoro-7^-[ctt-4-(4-methyl-qumolin-
2-ylamino)-cyclohexyI]-benzamide (3.52 g) as colorless solid. To a solution of 3,4-difluoro-Ar-[cw-4-
(4-methyl-quinolin-2-yIamino)-cyclohexyl]-benzamide (700 mg) in EtOH (7 mL) was added MsOH
(179 mg). The mixture was stirred at ambient temperature for 3 hr. The precipitate was collected by
filtration, washed with EtOH, and dried at 70 °C under reduced pressure to give 3,4-difIuoro-/V-
[c/s-4-(4-methyl-quinolin-2-yIamino)-cyclohexyl]-benzamide methanesulfonic acid (769 mg) as a
white solid.
ESI MS m/e 396, M (free) + H+; lH NMR (300 MHz, DMSO-d6) 6 1.69-2.01 (m, 8 H), 2.42 (s, 3 H),
2.62 (brs, 3 H), 3.90-4.21 (m, 2 H), 7.02-7.13 (m, 1 H), 7.47-7.61 (m, 2 H), 7.75-8.04 (m, 5 H), 8.35,
(d,y= 6.4 Hz, 1 H), 9.15-9.42 (m, 1 H), 12.27-12.51 (m, 1 H).

750
Example 3239
3-Chloro-4-fluoro-7V-[C1-5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyll-benzamide
methanesulfonic acid
Step A: Synthesis of 3-chloro-4-(luoro-Ar-[m-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
benzamide methanesulfonic acid.
To a solution of 3-chIoro-4-fluoro-benzoic acid (2.26 g) and iV-(c«-4-methyl-quinolin-2-yl)-
cyclohexane-l,4-diamine obtained in step A of example 3070 (3.00 g) in DMF (30 mL) were added
Et3N (3.93 mL), HOBt-H2O (2.70 g), and EDC-HCI (2.47 g). The reaction mixture was stirred at
ambient temperature for 6 hr. To the reaction mixture was added water (200 mL) and the suspension
was stirred at ambient temperature for 30 min. The precipitated was collected by filtration, washed
with H2O, and purified by medium-pressure liquid chromatography (NH-silica gel, 20% to 33%
EtOAc in hexane) to give 3-chIoro-4-fluoro-A/:-[cz5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
benzamide (4.40 g) as a colorless solid. To a solution of 3-chloro-4-fluoro-Ar-[czs-4-(4-methyl-
quinoIin-2-ylamino)-cyclohexyI]-benzamide (800 mg) in EtOH (8 mL) was added MsOH (196 mg).
The mixture was stirred at ambient temperature for 4 hr. The precipitate was collected by filtration,
washed with EtOH, and dried at 80 °C under reduced pressure to give 3-chloro-4-fluoro-Ar-
[cz.y-4-(4-methyl-quinolin-2-ylamtno)-cyC1-5hexyl]-benzamide methanesulfonic acid (845 mg) as a
white solid.
ESI MS m/e 434, M (free) + Na+; 'H NMR (300 MHz, DMSO-d6) 5 1.66-1.99 (m, 8 H), 2.38 (s, 3 H),
2.56-2.73 (m, 3 H), 3.87-4.21 (m, 2 H), 6.99-7.14 (m, 1 H) 7.48-7.58 (m, 2 H), 7.74-7.84 (m, 1 H),
7.87-8.05 (m, 3 H), 8.12 (dd, 7= 7.2, 2.2 Hz, 1 H), 8.36-8.41 (m, 1 H), 9.14-9.39 (m, 1 H),
12.28-12.55 (m, 1H).
Example 3240
3-Methoxy-7V-[c«-4-(quinolin-2-yIamino)-cyclohexyl]-benzamide methanesulfonic acid

751
Step A: Synthesis of 3-methoxy-A^[cw-4-(quinolin-2-ylamino)-cyC1-5hexyl]-benzamide
methanesulfonic acid.
To a solution of c/5-7V-quinolin-2-yI-cyclohexane-l,4-diamine obtained in step A of example
3033 (4.00 g) in CHC13 (40 mL) were added Et3N (4.85 mL) and 3-methoxy-benzoyl chloride (3.10
g). The mixture was stirred at ambient temperature for 6 hr. The reaction was quenched with
saturated aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (three times). The
combined organic layer was dried over MgSO4, filtered, concentrated under reduced pressure, and
purified by medium-pressure liquid chromatography (NH-silica gel, 20% EtOAc in hexane) to give
3-methoxy-/V-[ c^-4-(quinoIin-2-ylamino)-cyclohexyl]-benzamide (5.42 g) as colorless solid. To a
solution of 3-methoxy-7v"-[ c/s-4-(quinolin-2-ylamino)-cyclohexyI]-benzamide (700 mg) in EtOH (7
mL) was added MsOH (188 mg). The mixture was stirred at ambient temperature for 24 hr. The
precipitate was collected by filtration, washed with EtOH, and dried at 80 °C under reduced pressure
to give 3-methoxy-AL[c/5-4-(quinoIin-2-ylamino)-cyclohexyl]-benzamide methanesulfonic acid (741
mg) as a white solid.
ESI MS m/e 398, M (free) + Na+; 'H NMR (300 MHz, DMSO-d6) 5 1.70-1.99 (m, 8 H), 2.35 (s, 3 H),
3.81 (s, 3 H) 3.90-4.04 (m, 1 H), 4.08-4.22 (m, 1 H), 7.06-7.26 (m, 2 H), 7.32-7.56 (m, 4 H), 7.73-8.02
(m, 3 H), 8.17-8.38 (m, 2 H), 12.41-12.58 (m, 1 H).

752
Example 3241
A^cis-4^(4-Amino-5~methylpyriniidin-2--yl)amino]cyclohexyI}-3,5-
bis(trifluoromethyl)benzamide hydrochloride
Step A: Synthesis of 2-chloro-5-methyl-pyrimidin-4-ylamine.
A solution of 2,4-dichloro-5-methyI-pyrimidine (4.1 g, 0.025 mol) was dissolved in THF (30
mL) and cooled with stirring on an ice bath. To the mixture was added 7 N NH3 in MeOH (14.4 mL,
0.10 mol) and stirring was continued overnight (in which time the ice melted and the reaction warmed
to room temperature). The excess solvent was removed in vacuo and the precipitate was suspended in
CH2C12 (20 mL). The organic layer was extracted with a NaHCO3 (aq) solution (20 mL) and both
layers of the extraction were filtered to collect the resulting insoluble precipitate. This precipitate was
washed with cold H2O and dried to yield 2-chloro-5-methyl-pyrimidin-4-ylamine (1.0 g, 0.0070 mol,
27 %) as a white solid.
ESI-MS m/e 144.2 M+H"; 'HNMR (400 MHz, DMSO-d6) 5 7.80 (s, 1H), 7.22 (bs, 2H), 1.93 (s, 3H).
Step B: Synthesis of Ar-{cis-4-[(4-amino-5-methylpyrimidin-2-yl)amino]cyC1-5hexyl}-3,5-
bis(trifluoromethyl)benzamide hydrochloride.
To a solution of 2-chloro-5-methyl-pyrimidin-4-ylamine (292 mg, 2.03 mmol) in 2 mL 2-
propanol was added DIEA (531 uL, 3.05 mmol) and m-JV-(4-amino-cyclohexyl)-3,5-
bis(trifluoromethyl)-benzamide (720 mg, 2.03 mmol). The mixture was then heated in a microwave at
170 °C for 1 hour. The reaction mixture was cooled and concentrated and the resulting oil was purified
by column (0-5 % MeOH in CH2C12). The organic solvents were evaporated and the resulting oil was
re-dissolved into 4 mL CH2C12 and 2M HC1 in Et2O (2.0 mL, 4.0 mmol) was added. The reaction was
stirred for 30 minutes and the solvent was removed. A precipitate formed that was subsequently
filtered and washed with a cold 50% ether in hexanes solution to yield A/-{cis-4-[(4-amino-5-

753
methylpyrimidin-2-yl)amino]cyclohexyl}-3,5-bis(trifluoromethyl)benzamide hydrochloride (500 mg,
1.00 mmol, 49%) as a HC1 salt.
ESI-MS m/e 462.2 M+H+ ; 'HNMR (400 MHz, DMSO-d6) 6 11.86 (s, 1H), 8.79 (s, 1H), 8.51 (s, 1H),
8.39 (s, 1H), 8.31 (s, 1H), 8.01 (s, 1H), 7.85 (s, 1H), 7.66 (s, 1H), 3.90 (bs, 2H), 1.90 (s, 3H), 1.89-1.61
(m, 8H).
Example 3242
2-[(ciy-4-{[4-(Dimethylamino)-5-methylpyrimidin-2-yI]amino}cyC1-5hexyl)aiiiino]-l-[4-
(trifluoromethoxy)phenyl]ethanone trifluoroacetate
Step A: Synthesis of 2-[(cw-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)amino]-l-[4-(trifluoromethoxy)phenyl]ethanone trifluoroacetate.
To a solution of c/5-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-l-cyclohexylamine
(37 mg, 0.14 mmol) and 4-trifluoromethoxy bromoacetophenone (42 mg, 0.14 mmol) in THF (2 mL)
was added DIEA (20 jaL). The reaction was stirred for 2 h at 65 °C, concentrated, dissolved in DMSO
(1 mL), and purified by prep-HPLC to give 2-[(c/s-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)amino]-l-[4-(trifluoromethoxy)phenyl]ethanone trifluoroacetate 24 mg (30 %) as
a white powder.
ESI-MS m/e 452 (M + H)+; 'H NMR (400 MHz, CDC13) 8 8.28 (bs, 2 H), 8.09 (d, 2 H, J = 8.8 Hz),
7.29 (m, 2 H), 7.20 (m, 1 H), 4.13 (bs, 1 H), 3.45 (bs, 1 H), 3.33 (s, 6 H), 3.27 (bm, 2 H), 2.28 (s, 3 H),
2.02-1.71 (m,8H).
Example 3243

754
7V-{l-[3,5-Bis(trifluoromethyl)phenyl]-l-methylethyl}-N'-(c/y-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)urea trifluoroacetate
Step A: Synthesis of iV-{l-[3,5-bis(trifluoroinethyl)phenyl]-l-methylethyl}-N'-(cw-4-{[4-
(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)urea trifluoroacetate.
To a solution of 2-(3,5-bistrifluoromethyl-phenyl)-2-methyl propionic acid (0.4 g, 1.3 mmol)
and Et3N (0.17 mL, 1.3 mmol) in dry benzene (4 mL) was added diphenylphosphoryl azide (0.36 g,
1.3 mmol). During the reaction being refluxed for about 3 h, 3,5-bistrifluoromethyI-4-(isocyanato-l-
methyl-ethyl)-benzene was formed as the reaction intermediate, which was directly used to prepare
urea derivatives.
To a solution of c/5-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-l-aminocyclohexane
(40 mg, 0.16 mmol) in EtOH (1 mL) was added 3,5-bistrifluoromethyl-4-(isocyanato-l-methyl-ethyl)-
benzene (48 mg, 0.16 mmol) from the above reaction. The reaction mixture was stirred at 60 °C for 1
h, and completed consumption of the starting material was observed by LC-MS. After removal of the
volatile solvent, the residue was dissolved in DMSO (1.5 mL) and purified by prep-HPLC to give 35
mg (35 %) of JV-{l-[3,5-bis(trifluorornethyl) phenyl]-l-methylethyl}-N'-(^-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino} cyclohexyl)urea trifluoroacetate.
ESI-MS m/e 547 (M + H)+; 'HNMR (400 MHz, CDC13) 5 13.4 (bs, 1 H), 8.37 (bd, 1 H, J = 6.4 Hz),
7.84 (s, 3 H), 7.71 (s, 1 H), 5,56 (bs, 1 H), 4.01 (bs, 1 H), 3.75 (m, 1 H), 3.29 (s, 6 H), 2.25 (s, 3 H),
1.75-1.60 (m, 14 H).
Example 3244
Ar-{l-[3,5-Bis(trifluoromethyI)phenyl]-l-methylethyl}-iV-(c/5-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)-./V-methylurea trifluoroacetate

755
Step A: Synthesis of iV-{l-[3,5-bis(trinuoromethyl)phenyl]-l-methylethyl}-iV-(c«-4-{[4-
(dimethylamino^S-methylpyrimidin-Z-ylJaminoJcyC1-5hexyO-A^methylurea trifluoroacetate.
3,5-Bistrifluoromethyl-4-(isocyanatO"l-methyI-ethyl)-benzene (36 mg, 0.12 mmol) was added
to a solution of c/5-4-(4-dimethyIamino-5-methyl-pyriniidin-2-ylamino)-l-aminocyclohexane (30 mg,
0.12 mmol) and CH3I (0.17 g, 1.2 mmol) in anhydrous benzene (1 mL) under an inert atmosphere.
The reaction mixture was stirred at 50 °C for 2 h, and formation of the methylated and protonated
products were observed by LC-MS. After removal of the volatile solvent, the residue was dissolved in
DMSO (1.5 mL) and purified by prep-HPLC. 20 mg (25 %) of Ar-{l-[3,5-bis(trifluoromethyl)phenyl]-
l-methylethyl}-A/I-(c/5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-Ar-
methylurea trifluoroacetate was isolated as a white powder.
ESI-MS m/e 561 (M + H)+; *H NMR (400 MHz, CDC13) 5 14.5 (bs, 1 H), 9.19 (bd, 1 H, J = 6.0 Hz),
7.84 (s, 2 H), 7.79 (s, 1 H), 7.70 (s, 1 H), 4.87 (s, 1 H), 4.23 (bs, 1 H), 4.14 (m, 1 H), 3.26 (s, 6 H), 2.98
(s, 3 H), 2.23 (s, 3 H), 1.75-1.65 (m, 14 H).
Example 3245
c/5-AL{l-[3,5-Bis(trifluoromethyl)phenyI]-l-inethylethyl}-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyC1-5hexanecarboxamide trifluoroacetate
Step A: Synthesis of l-(3,5-bistrifluoromethyl-phenyl)-l-methyl-ethylamine.
3,5-Bistrifluoromethyl-4-(isocyanato-l-methyl-ethyl)-benzene(0.1 g, 0.33 mmol) was treated
with 8-N HC1 (4 mL). The acidic aqueous solution was heated for 1 h at 60 °C. After cooling the
reaction, NaOH pellets were added to make the aqueous mixture alkaline. The solid precipitates were
filtered off, and the basic aqueous was extracted with DC1-5 (2x). The combined organic was washed
with H2O, dried, and concentrated to give l-(3,5-bistrifluoromethyl-phenyl)-l-methyl-ethylamine: 1-

756
(3,5-bistrifluoromethyl-phenyl)-l-methyl-ethylamine appeared to be unstable in neat. The product was
kept in DC1-5 solution.
ESI-MSm/e272(M + H)+
Step B: Synthesis of cw-Ar-{l-[3,5-bis(trifluoromethyl)phenylJ-l-methylethyl}-4-{[4-
(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexanecarboxamide trifluoroacetate.
To a solution of c/s-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexanecarboxylic acid (15 mg, 0.05 mmol) and l-(3,5-bistrifIuoromethyl-phenyl)-l-methyl-
ethylamine (15 mg, 0.05 mmol) in DC1-5 (1.5 mL) was added HATU (25 mg, 0.06 mmol) and followed
by Et3N (10 mg, 0.1 mmol). After 4h stirring at room temperature, the reaction was concentrated,
dissolved in DMSO (1.5 mL), and purified by prep-HPLC to give 11 mg (30 %) of cw-iV-{l-[3,5-
bis(trifluoromethyl)phenyl]-l-methylethyl}-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yljamino} cyclohexanecarboxamide trifluoroacetate.
ESI-MS m/e 532 (M + H)+; lH NMR (400 MHz, CDC13) 5 14.6 (bs, 1 H), 8.64 (bd, 1 H, J = 6.0 Hz),
7.78 (s, 2 H), 7.69 (s, 1 H), 7.30 (d, 1 H, J = 7.2 Hz), 7.16 (s, 1 H), 4.40 (bs, 1 H), 3.30 (s, 6 H), 2.26 (s,
3 H), 2.18 (m, 1 H), 2.07-1.80 (m, 8 H), 1.70 (s, 6 H).
Example 3246
3,4-Difluoro-A/-{ciy-4-[(4-methoxy-5-methylpyrimidin-2-yl)amino]cyclohexyl}benzamide
trifluoroacetate
Step A: Synthesis of 2-chloro-4-methoxy-5-methyl pyrimidine.
2,4-dichloro-5-methyl pyrimidine (0.8 g, 5 mmol) was dissolved in MeOH (10 mL), and 0.5
M-NaOCH3 in MeOH (10 mL, 5 mmol) was slowly added into the solution. The reaction was stirred
for 40 min at room temperature, diluted with H?O, and extracted with DC1-5 (3x). The combined

757
organic was washed with H20 (2x) and saline (Ix), dried, and concentrated. 0.8 g (99 %) of 2-chIoro-
4-methoxy-5-methyl pyrimidine was isolated, which was directly used for the next reaction without a
further purification.
^NMR^OO MHz, CDC13) 5 8.10 (s, 1 H), 4.03 (s, 3 H), 2.12 (s, 3 H).
Step B: Synthesis of N-[cw-4-(4-methoxy-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]carbamic
acid tert-butyl ester.
A sealed tube containing 2-chloro-4-methoxy-5-methyl pyrimidine (0.35 g, 2.2 mmol), cis-(4-
amino-cyclohexyl)-carbamic acid tert-buty\ ester (0.56 g, 2.4 mmol), DIEA (0.8 mL, 4.5 mmol), and
IPA (2 mL) was reacted for 4000 sec at 175 °C in a Personal Microwave Synthesizer. The reaction
was diluted with DC1-5, washed with 1N-HC1 and H?O, dried, and concentrated. The crude product
was purified by column chromatography [silica gel, DC1-5:MeOH (100:0 to 97:3)]. 0.25 g (34 %) of
N-[cw-4-(4-methoxy-5-methyl-pyrimidin-2-ylamino)-cyclohexyl] carbamic acid ter/-butyl ester was
isolated.
ESI-MS m/e 337 (M + H)+; !H NMR (400 MHz, CDC13) 5 7.80 (s, 1 H), 4.86 (bd, \H,J= 6.0 Hz),
4.55 (bs, lH),3.93(bm, 1 H), 3.89 (s, 3 H), 3.62 (bs, 1 H), 1.97 (s, 3 H), 1.83-1.55 (m, 8 H), 1.45 (s, 9
H).
Step C: Synthesis of c/s-4-(4-methoxy-5-methyl-pyrimidin-2-ylainino)-aminocyC1-5hexane.
To a solution of N-[c/5-4-(4-methoxy-5-methyl-pyrimidin-2-ylamino)-cyclohexyl] carbamic
acid /e/7-butyl ester (0.24 g, 0.7 mmol) in DC1-5 (10 mL) was added TFA (5 mL). The reaction was
stirred for 1.5 h at room temperature. After removal of the volatile solvent, the residue was treated
with 4N-NaOH (3 mL). The basic aqueous was extracted with DC1-5 (3x), and combined organic was
washed with H2O (2x) and brine (lx), and concentrated. 0.13 g (82 %) of cis-4-(4-methoxy-5-methyl-
pyrimidin-2-ylamino)-aminocyclohexane was isolated as a yellowish solid.

758
ESI-MS m/e 237 (M + H)+; !H NMR (400 MHz, CDC13) 5 7.79 (s, 1 H), 5.05 (bd, 1 H, J = 6.4 Hz),
3.99 (bs, 1 H), 3.89 (s, 3 H), 2.92 (bm, 1 H), 2.45 (bs, 2 H), 1.96 (s, 3 H), 1.83-1.45 (m, 8 H).
Step D: Synthesis of S^-difluoro-A^c/s^-^-methoxy-S-methylpyrimidin-Z-
yl)amino]cyclohexyl}benzamide trifluoroacetate.
To a solution of c/5-4-(4-methoxy-5-methyI-pyrimidin-2-ylamino)-aminocyclohexane (20 mg,
0.08 mmol) in DC1-5 (1 mL) was added 3,4-difluorobenzoyl chloride (14 mg, 0.08 mmol), and
followed by Et3N (25 ^L). The reaction was stirred for 2 h at room temperature, and MeOH (0.2 mL)
was added to quench the reaction. After removal of the volatile solvent, the residue was dissolved in
DMSO (1.5 mL) and purified by prep-HPLC to give 12 mg (40 %) of 3,4-difluoro-Ar-{c/s-4-[(4-
methoxy-5-methylpyrimJdin-2-yl)amino]cyclohexyl}benzamide trifluoroacetate as a white powder.
ESI-MS m/e 377 (M + Rf; !H NMR (400 MHz, CDC13) 5 15.7 (bs, 1 H), 9.55 (d, 1 H, J = 7.2 Hz),
7.73 (m, 1 H), 7.59 (m, 1 H), 7.57 (s, 1 H), 7.20 (m, 1 H), 6.80 (d, lH,/= 8.0 Hz), 4.37 (bs, 1 H),
4.18 (bm, 1 H), 4.09 (s, 3 H), 2.04 (s, 3 H), 1.89-1.75 (m, 8 H).
Example 3247
-/V-(m-4-{[4-MethyI-6-(methylamino)pyrimidin-2-yl]amino}cyC1-5hexyI)-4-
(trifluoromethoxy)benzamide hydrochloride
Step A: Synthesis of (2-chloro-6-methyl-pyrimidin-4-yl)-methyl-amine.
2,4-Dichloro-6-methylpyrirnidine (10 g, 61.34 mmol) in 50 mL in CH2C12 was added 2 M
methylamine in methyl alcohol (46.01ml, 92.02 mmol) at 0°C. The reaction mixture was stirred
overnight and then the excess solvent was evaporated off and the material subjected to chromatography
(50% hexanes in ethyl acetate) to yield (2-chloro-6-methyl-pyrimidin-4yl)-methyl-amine (5.835 g,
37.17 mmol, 60.59%) as a white solid.

759
ESI-MS 158.0 M+JT ; 'HNMR(400 MHZ, DMSO-d6) 5 7.62 (s, 1H), 6.18 (s, 1H), 2.70 (bs, 3H), 2.10
(bs, 3H).
Step B: Synthesis AL(m-4-{[4-methyl-6-(methylamino)pyrimidin-2-yl]amino}cyclohexyl)-4-
(trifluoromethoxy)benzamide hydrochloride.
To a solution of (2-chIoro-6-methyl-pyrimidin-4yl)-methyl-amine (500 mg, 3.18 mmol) in 3
mL 2-propanol was added c/5-Ar-(4-amino-cyclohexyl)-4-trifluoromethoxy-benzamide (1.25 g, 4.14
mmol) andDIEA (1.108 mL, 6.36 mmol). The mixture was heated in a microwave synthesizer at 180
°C for 2 hours. The solvent was evaporated and obtained compound was dissolved in CH2C]2 and was
added 2 M HC1 in diethyl ether (6.2 mL) to give A4cw-4-{[4-methyl-6-(methylamino)pyrimidin-2-
yl]amino}cyclohexyi)-4-(trifluoromethoxy)benzamide hydrochloride (1.3014 g, 2.83 mmol, 89 %) as a
yellowish solid.
ESI-MS 424.2 M+H*; *H NMR (400 MHz, DMSO-d6) 5 8.72 (s, 1H), 8.44 (s, 1H), 7.99-7.96 (d, J= 8
Hz, 2H), 7.86 (s, 1H), 7.47-7.45 (d, /= 8 Hz, 2H, 4.03 (s, 1H), 3.87 (s, 1H), 2.89-2.88 (d, 7=4 Hz, 3H),
2.20 (s, 3H), 1.85 (bs, 2H), 1.72 (bs, 6H).
Example 3248
A'-({ci.s-4-[(4-Amino-5-methylpyrimidin-2-yl)ainino3cyclohexyl}methyI)-3,5-
bis(trifluoromethyl)benzamide hyd rochloride
Step A: Synthesis of 7V-({m-4-[(4-amino-5-methylpyrimidin-2-yl)aminolcyclohexyl}methyl)-3,5-
bis(trifluoromethyl)benzamide hydrochloride.
To a solution of 2-chloro-5-methyl-pyrimidin-4-ylamine (269 mg, 1.87 mmol) in 1 mL 2-
propanol was added c/5-jV-(4-amino-cyclohexylmethyl)-3,5-bis4rifluoromethyl-benzamide (689.8 mg,
1.87 mmol) and DIEA (489.5.4 JJ.1, 2.81 mmol). The mixture was heated in a microwave synthesizer at

760
180 °C for 2 hours. The solvent was evaporated and the material subjected to chromatography (1 -2%
methanol/ CH2CI2) The obtained compound was dissolved in CH2C12 and was added 2 M HC1 in
diethyl ether (2.2 mL) to give A^-({cj5-4-[(4-amino-5-methyIpyrimidin-2-
yl)amino]cyC1-5hexyl}methyl)-3,5-bis(trifluoromethyl)benzamide hydrochloride (667.1 mg, 1.30 mmol,
70%) as a white solid.
ESI-MS 476.2 M+H+ ; 'H NMR (400 MHz, DMSO-d6) 5 9.16-9.13 (t, J= 4 Hz, J= 8 Hz, 1H), 8.55 (s,
2H), 8.36-8.31 (bs, 2H), 7.86 (bs, 1H),7.71 (bs, lH),4.07(bs, 1H), 3.27-3.24 (t,J= 8 Hz, J = 4 Hz,
2H), 1.91 (bs, 3H), 1.73-1.42 (m, 8H).
Example 3249
2-[(2-Chlorophenyl)sulfonyl]-Ar-(c«-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide trifluoroacetate
Step A: Synthesis of c/s-2-chloro-A^4-(4-dimethylamino-6-methyl-pyrimidin-2ylamino)-
cyclohexylj-nicotinamide.
c/5-Ar2-(4-Amino-cyclohexyI)-6, JV',-/V/-trimethyl-pyrimidine-2,4-diamine (2.86 g, 11.5 mmol)
in 20 mL CH2Cl2was added 2-chloronicotinoyl chloride (2.02 g, 11.5 mmol), and DIEA (3.9 mL, 23
mmol). The reaction mixture was stirred for an hour. The solvent was evaporated off and the
compound was crystallized (2% hexanes in ether) to yield c/.s-2-chloro-./V-[4-(4-dirnethylamino-6-
methyl-pyrimidin-2ylamino)-cyclohexyl]-nicotinamide (4.2 g, 10.8 mmol, 94%).
ESI-MS 389.2 M+H"; lH NMR (400 MHz, DMSO-d6) 6 13.1 (bs, 1H), 8.72-8.70 (d,J= 8 Hz, 1H),
8.49-8.46(dt,/=8Hz,l/=4Hz, 1H), 8.04 (s, 1H), 7.89-7.87 (dd, J= 4 Hz, J= 4Hz, 1H), 7.52-7.47 (q,
7= 8 Hz, J=4Hz, 1H), 6.27 (s, 1H), 3.95 (bs, 2H), 3.27 (bs, 6H), 2.31 (s, 3H), 1.82-1.74 (m, 8H).

761
Step B: Synthesis of 2-[(2-chlorophenyl)sulfonyl]-Ar-(c/s-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yl]amino}cyclohexyI)nicotinamide trifluoroacetate.
To a solution of c/5-2-chloro-iV-[4-(4-d imethylami no-6-m ethyl-pyri mid in-2y lam in o)-
cyclohexylj-nicotinamide (50 mg, 0.128 mmol) in 1 mL dioxane was added 2-chlorobenzenethioI (37.1
mg, 0.256 mmol), and Cs2CO3 (83.4 mg, 0.256 mmol). The mixture was heated in a microwave
synthesizer at 180 °C for 1 hour. After the solvent was evaporated, the compound was then subjected to
purification by prep HPLC to give c/5-2-(2-chloro-phenylsulfanyl)-iV-[4-(4-dimethylamino-6-methyl-
pyrimidin-2-ylamino)-cyclohexyl]-nicotinamide trifluoroacetate (23.2 mg, 30 %) as a white solid.
ESI-MS m/e 497.4 M+lT ;
To a solution of c/5-2-(2-chloro-phenyIsulfanyl)-7V-[4-(4-dimethylamino-6-methyl-pyrimidin-
2-ylamino)-cyclohexyl]-nicotinamide trifluoroacetate (23.2 mg, 0.038 mmol) in lmL CHiCU was
added 3-chloroperoxybenzoic acid (31.5 mgO.14 mmol). The reaction mixture was stirred for 15 h and
quenching with NaHCO3. The solvent was evaporated and compound was then subjected to
purification by prep HPLC to give 2-[(2-chlorophenyl)sulfonyl]-A'-(cw-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yl]amino}cyC1-5hexy!)nicotinamide trifluoroacetate (8.9 mg, 0.014 mmol, 36%) as a
white solid.
ESI-MS m/e 529.2 M+H+ ; !H NMR (400 MHz, DMSO-d6) 5 11.98 (s, 1H), 8.61-8.59 (m, 2H), 8.24-
8.21 (dd, J= 4 Hz, 4 Hz, 1H), 8.08-8.06 (d, J= 8Hz, 1H), 7.79-7.74 (m, 2H), 7.71-7.69 (t, J= 4Hz,
1H), 7.64-7.62 (d, J= 8 Hz, 1H), 7.58 (bs, 1H), 6.32 (s, 1H), 3.94 (bs, 2H), 3.2l(s, 3H), 3.15 (s, 3H),
2.28 (s,3H), 1.84-1.78 (m, 8 H).
Example 3250
A/-(c/5-4-{[(4-MethylquinoIin-2-yI)methyl]amino}cyclohexyl)-3,5-bis(trifluoromethyl)ben2amide
trifluoroacetate

762
Step A: Synthesis of 4-methyl-2-vinyl-quinoline.
To 50 mL toluene in a 150 mL rounded-bottom flask, was added 2-chlorolepidine (1 g, 63
mmol), tetrakis (triphenylphonsine ) palladium (0) (65 mg, 0.63 mmol), triphenyl phosphine (0.495 g,
1.89 mmol) and vinyltributyl tin (2.2 g,6.76 mmol). The mixture was refluxed at 116 °C under N? for 2
hours. The reaction mixture was concentrated and purified by silica gel with 0-10% EtOAc/Hexane to
yield 4-methyl-2-vinyl-quincline (720 mg, 4.26 mmol, 76%).
ESI MS m/e: 170.0 M+H+; 'H NMR (400 MHz, CDC13) 5 7.96 (d, J= 8 Hz,lH), 7.85 (d, J= 8 Hz,
1H), 7.58(dd,Ji= J2=8Hz, 1H), 7.43 (dd,y,- J2=8Hz, 1H), (7.15 (s, 1H), 6.89 (dd,J,= 16 Hz,
J2= 12 Hz, 1H), 6.15 (d, J = 16 Hz, 1H), 5.54 (d, J= 8 Hz, 1H), 2.60 (s, 3H)
Step B: Synthesis of 4-methyl-quinoline-2-carbaldehyde.
To a 500 mL rounded bottom flask filled with 40 mL 90% THF/H2O was added 4-methyl-2-
vinyl-quinoline (1.2 g, 7.1 mmoI)NMO (1.29 g, 10.65 mmol), and OsO4 (1.3 mL, 0.21 mmol) under
N2. The mixture was stirred at room temperature overnight under N2. The reaction mixture was
quenched with saturated solution of Na2S2O3 , and the organic phase was then extracted EtOAc (100
mL x 4. The organic layer was combined and washed with brine, and concentrated. The crude product,
l-(4-methyl-quinolin-2-yI)-ethane-],2-diol (1.5 g), was directly used to next Step without further
purification.
To 60 mL 90%THF/H2O, was added 1.5 g of the crude l-(4-methyI-quinolin-2-yl)-ethane-l,2-dioI and
NaIO4 (1.4 g, 8.86 mmol). The mixture was stirred at room temperature under N2 for 6 hours. The
organic phase was extracted with EtOAc (100 mL x4, combined, and dried by anhydrous MgSO4. It
was concentrated to purify by silica gel column using 0-5% EtOAc /Hexane to yield 4-methyl-
quinoline-2-carbaldehyde (600 mg, 3.5 mL, 49.4%).
ESI MS m/e: 172.0 M+rf; ]H NMR (400 MHz, CDC13) 6 10.2 (s, 1H), 8.25 (d, J= 8 Hz, 1H), 8.07 (d,
J= 8 Hz, 1H), 7.88 (s, 1H), 7.82 (dd, 7, = J2= 8 Hz, 1H), 7.71 (dd, Jl = J2= 8 Hz, 1H), 2.79 (s, 3H).

763
Step C: Synthesis of resin bound cfr-(4-amino cyclohexyl) carbamic acid fluorenylmethyl ester.
In a 30 mL manual synthesis vessel, 2-(3,5 dimethoxy-4-formyl) phenoxy ethyl polystyrene
resin (0.5 gram; 0.90 mmol/gram) and c/.s-(4-amino cyclohexyl) carbamic acid fluorenylmethyl ester 2
(453mg, 1.35 mmol) were suspended in 4 mL of DMF. To this suspension was added a solution of
NaBH(OAc)3 (299 mg, 1.35 mmol) in 1% acetic acid/DMF solution (4 mL). After shaking the mixture
overnight in a rotary shaker, the solution was removed by filtration and the resin washed sequentially
with DMF, 10% DIEA/DMF, DMF, DC1-5 and MeOH. The washing sequence was repeated four times.
The resulting resin bound intermediate was dried under vacuum for 20 minutes.
Step D: Synthesis of resin bound-cfr -[4- (4- methyl-quinolin-2-methyl-amino)-cyclohexyl]-
carbamic acid flourenylmethyl ester.
To the resin bound intermediate (0.315 mmol) was added 4-methyI-quinoline-2-carbaIdehyde
(96 mg, 0.564 mmol) in dimethyl acetamide (5 mL) and 1% acetic acid (.050 mL). The resin
suspension was mixed in a rotary shaker for 1 hour at room temperature. Sodium cyanoborohydride
(195 mg, 3.15 mmol) was added to the resin suspension and the reaction was mixed overnight at room
temperature. At the completion of the reaction, the solution was filtered and the resin washed
sequentially with DMF, 10%DIEA/DMF, DMF, DC1-5 and MeOH. The washing sequence was
repeated four times. The resulting resin bound intermediate 5 was dried under vacuum for 20 minutes
Step E: Synthesis of AL(c«-4-{[(4-methylquinolin-2-yl)methyl]amino}cyC1-5hexyl)-3,5-
bis(trifluoromethyl) benzamide trifluoroacetate.
The resin bound intermediate (0.171 mmol) was treated with 20% piperidine in DMF (3 mL)
for 30 minutes at room temperature. After 30 minutes, the solution was filtered and the resin washed
with DMF, DC1-5 and MeOH. The washing sequence was repeated four times.
The deprotected resin bound intermediate was suspended in DMF (1.0 mL). 3,5 bis-
trifluoromethylbenzoyl chloride (47 mg, 0.171 mmol) was added to the resin suspension followed by

764
triethylamine (0.0519 mL, 0.513 mmol). The reaction was mixed for 30 minutes at room temperature.
The solution was then filtered and the resin washed sequentially with DMF, DC1-5 and MeOH. The
washing sequence was repeated four times.
After drying under vacuum for 20 minutes, the resin bound intermediate was treated with 5 mL
of TFA solution (TFA /CH2C12 /H20 20:20:1 v/v). The reaction was shaken for 2 hours and the TFA
solution was collected after filtration. The TFA was removed by rotary evaporation and the compound
subjected to purification by preparative HPLC to give iV-(c/5-4-{[(4-methyl quinolin-2-
yl)methy!]amino}cyclohexyl)-3,5-bis(trifluoromethyl)benzamide trifluoroacetate (3.8 mg; 8%) as a
white solid.
ESI MS m/e 510.2 M+H+; 'H NMR (400MHz, CD3OD) 5 (ppm): 8.56 (m, 1H), 8.42 (s, 2H), 8.19 (m,
3H), 7.82 (m, 1H), 7.69 (m, 1H), 7.39 (s, 1H), 4.6 (s, 2H), 4.14 (m, 1H), 3.40 (m, 1H), 2.78 (s, 3H),
2.22-1.81 (m,8H).
Example 3251
C1-5-Ar-[(15)-l-(4-Chlorophenyl)ethyl]-4-{[4-(dimethylamino)-5-methylpyriinidin-2-
yl)amino}cyclohexanecarboxamide trifluoroacetate
Step A: Synthesis of C1-5-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexanecar boxy lie acid.
A mixture of (2-chIoro-5-methyl-pyrimidin-4-yl)-dimethyl-amine (28.9 g, 0.186 mol) and 4-
amino-cyclohexanecarboxylic acid (20 g, 0.140 mol) in 100 mL of toluene was stirred at room
temperature for 5 minutes to form a slurry under N2. To the slurry, was added Pd(OAc)2 (0.34 g, 1.5 x
10"3 mol), 2-(di-t-butylphosphine) biphenyl (0.24, 0.8 mmol) and NaOtBu (33.64 g, 0.35 mol). The
mixture was heated and refluxed at 118 °C under N2 for 2 hours. The reaction mixture was
concentrated to give a brown solid. The above brown solid was dissolved with 100 mL MeOH and 5

765
mL H20, neutralized with acetic acid. The precipitate was filtered and washed with cold water (5mL x
2) and toluene (100 mL x 2) to yield cw-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexanecarboxylic acid (36.7 g, 0.132 mol, 94%) as a white solid.
ESI MS m/e 279 M+H+; !H NMR (400 MHz, CDC13) 6 7.46 (s, 1H), 4.20 (s, 1H), 3.3 (s, 6H), 3.2 (s,
1H), 2.48 (m, 1H), 2.27 (s, 3H), 2.15-1.63 (m, 8H).
Step B: Synthesis of c/s-iV-[(15)-l-(4-chlorophenyl)ethyl]-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexanecarboxamide trifluoroacetate.
To a solution of (S)-l-(4-chloro-phenyl)-ethylamine (61.5 mg, 0.395 mmol) in 10 mL DC1-5
was added c/s-4-(4-dimethyIamino-5-methyl-pyrimidin-2-ylamino)-cyclohexanecarboxylic (100 mg,
0.395 mmoi), HATU (150 mg, 0.395 mmol), and 5 drops of Et3N. The reaction mixture was stirred at
room temperature under N2 overnight. The solvent was evaporated and the material subjected to prep-
HPLC to give c/s-Ar-[(15)-l-(4-chlorophenyl)ethyl]-4-{[4-(dimethyl amino)-5-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide trifluoroacetate (20 mg, 0.048 mmol, 13.4%) as a white solid.
ESI MS m/e 416.3 M+H+; 'HNMR(400 MHZ, DMSO-d6) 6 8.24-8.12 (d, 1H), 7.55 (s, 1H), 7.32-7.10
(m, 4H), 4.87 (m, 1H), 2.47 (s, 6H), 2.28 (bs, 1H), 2.18 (s, 3H), 1.81-1.39 (m, 8H), 1.31(d, 3H).
Example 3252
ci'5-Ar-[(17?)-l-(4-Bromophenyl)ethyl]-4-[(4-methylquinolin-2-yl)amino]cyC1-5hexanecarboxaniide
trifluoroacetate
Step A: Synthesis of c/s-4-(4-methyiquinolin-2-yIamino)cyclohexanecarboxyIic acid.
A mixture of 2-chloro-4-methyl-quinoline (6.67, 0.0375 mol) and 4-amino-
cyclohexanecarboxylic acid (4.48 g, 0.0312 mol) was dissolved in 100 mL of toluene and stirred at
room temperature for 5 minutes to form a slurry under N2. To the slurry, was added Pd(OAc)2 (0.077 g,

766
3.43x 10'4 mol), 2-(di-t-butylphosphine) biphenyl (0.093, 3.12X10"4 mol) and NaOtBu (7.5g, 0.078
mol). The above material was heated and refluxed at 118 °C for 2 hours. The reaction mixture was
concentrated under reduced pressure to give a brown solid. The above brown solid was dissolved with
100 mL MeOH and 5 mL H2O, neutralized with acetic acid. The precipitates were filtered and washed
with coid water (5 mL x 2) and toluene (100 mL x 2) to yield cw-4-(4-methylquinolin-2-
ylamino)cyclohexanecarboxylic acid (7.45 g, 0.026 mol, 84%) as a white solid.
ESI MS m/e 285.1 M+H+; ]H NMR (400 MHz, DMSO-d6) 5 7.78 (d, 1H), 7.49 (m, 1H), 7.21 (m, 1H),
6.85 (d, 1H), 6.72 (s, 1H)5 4.19 (s, 1H), 2,54-2.53 (m, 2H), 2.46 (s, 3H).
Step B: Synthesis of c«-Ar-[(lJR)-l-(4-bromophenyl)ethyl]-4-[(4-methylquinoliii-2-
yl)amino]cyclohexanecarboxamide trifluoroacetate.
To a solution of (i?)-l-(4-bromo-phenyl)-ethylamine (77.4 mg, 0.39 mmol) in 10 mL DC1-5
was added c/s-4-(4-methylquinolin-2-yIamino)cyclohexanecarboxylic acid (100 mg, 0.35 mmol),
HATU (148 mg, 0.39 mmol), and 5 drops of Et3N. The reaction mixture was stirred at room
temperature under N2 overnight. The solvent was evaporated and the material subjected to prep HPLC
to give cis-N-[( 17?)-1 -(4-bromophenyl)ethyl]-4-[(4-methylquinolin-2-yI)amino]
cyclohexanecarboxamide trifluoroacetate (24 mg, 0.052 mmol, 14.7%) as white solid.
ESI MS m/e 468.2 M+H"; ]H NMR (400 MHz, DMSO-d6) 5 9.18-9.07 (s, 1H), 7.94-7.84 (t, 1H), 7.74-
7.68 (t, 1H), 7.46-7.42 (m, 2H), 7.22-7.17 (m, 2H), 7.00-6.94 (s, 1H), 4.86 (m, 1H), 4.11 (s,lH), 2.58 (s,
3H), 2.40-2.23 (m, 2H), 1.88-1.49 (m, 8H), 1.33-1.19 (d, 3H).
Example 3253
/rrt«*-2-(4-Chlorophenyl)-Ar-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide trifluoroacetate

767
Step A: Synthesis of frfl«s-3-(4-chlorophenyl)-N-methoxy-N-methylacrylamide.
A solution of 4-chlorobenzalehyde (3 g, 21.34 mmol) and N-methoxy-N-methyl-2-
(triphenylphosphoranylidene)acetamide (8.5 g, 23.47 mmol) in CH2C12 was stirred at room
temperature for 16 h. The solvent was removed in vacuo, and the crude product was purified by
column chromatography on silica gel (0-20% EtOAc / Hex) to afford /ron^-3'(4-chIorophenyl)-N-
methoxy-N-methylacrylamide (4.78 g, 99%) as colorless crystals.
ESI MS m/e 226.1 M+H"; ]H NMR (400 MHz, CDC13) 5 7.66 (d, J= 5.6 Hz, 1H), 7.45 (d, J = 8.4 Hz,
2H), 7.33 (d, J= 8.4 Hz, 2H), 6.99 d,J= 5.6 Hz, 1H), 3.75 (s, 3H), 3.29 (s, 3H)
Step B: Synthesis of N-methoxy-N-methyl -trans-2-(4-ch\oropheny\) cyclo- propanecarbxoamide.
To a solution of trimethylsulfoxonium iodide (9.3 g, 42.4 mmol) in DMSO (40 mL) was added
sodium hydride (1.7 g, 42.4 mmol) at room temperature in portions. After 1 h, a solution of trans-3-(4-
chlorophenyl)-N-methoxy-N-methylaery 1 amide (4.78 g, 21.2 mmol) in DMSO (20 mL) was added via
cannula at r.t. The mixture was stirred for another 6 h, and then it was quenched with saturated aqueous
NH4C1 solution, extracted with CH2CI2, washed with brine and dried over anhydrous MgSO4. The
crude product was purified by column chromatography (0-50 % EtOAc / Hex)to afford N-methoxy-N-
methyl -/rtms-2-(4-chlorophenyl)cyclopropanecarboxamide as colorless oil (4.76 g, 88.5 %).
ESI MS m/e 239.9 M+H"; ]H NMR (400 MHz, CDCI3) 5 7.24 (d, J = 8 Hz, 2H), 7.06 (d, J= 8 Hz, 2H),
3.69 (s,3H), 3.23 (s, 3H), 2.47 (m, lH),2.37(bs, 1H), 1.63 (m, 1H), 1.27 (m, 1H)
Step C: Synthesis of #Yms-2-(4-chloro-phenyI)cyclopropanecarboxylic acid.
A suspension of afford N-methoxy-N-methyl -trans-2-(4-
chlorophenyl)cyclopropanecarboxamide (4.76 g, 18.76 mmol) and potassium tert-butoxide (4.76 g,
18.76 mmol) in the TBME (130 mL) and water (0.68 mL, 37.5 mmol) was stirred at room temperature
for I6h. The mixture was acidified by slowly adding concentrated HC1, and the aqueous mixture was
extracted with CH2C12 (3x60 mL). The combined organic layers were washed with brine and dried over

768
anhydrous MgSO4. The solvent was removed in vacuo and the product was obtained as white solid
(3.447 g, 93.5%)
ESI MS m/e 197.0 M+H+; 'H NMR (400 MHz, CDC13) 5 11.4 (bs, 1H), 7.28 (d, J= 8.4 Hz, 2H), 7.06
(d, J= 8.4 Hz, 2H), 2.60 (ddd, Jx = 9.5 Hz, J2 - 6.6 Hz, J3 = 4.1 Hz, 1H), 1.89 (ddd, J{ = 9.5 Hz, J2 =
5.2 Hz, J3 = 4.2 Hz, 1H), 1.69(dt,J;= 9.5 Hz, J2 = 5.1 Hz, 1H), 1.40 (ddd, Jx= 8.4 Hz, J2 = 5.2 Hz, J3
- 4.3 Hz, 1H)
Step D: Synthesis of/rfl«5-2-(4-chIorophenyl)-Ar-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide trifluoroacetate.
To a mixture of rra/w-2-(4-chloro-phenyI)cyclopropanecarboxylic acid (22.1 mg, 0.112 mmol) and 2-
chloro-4-dimethylamino-5-methyIpyrimidine (28 mg, 0.112 mmol) in CH2CI2 (5 mL) was added
HATU (42.6 mg, 0.112 mmol)at r.t. After 30 sec Et3N (5 drops) was added dropwise. The mixture was
stirred overnight. fra«5-2-(4-chlorophenyl)-A?-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide trifluoroacetate (20 mg, 37%) was obtained from
prep-HPLC.
ESI MS m/e: 428.4 M+JT; 'HNMR (400 MHz, CDC13) 6 8.49 (bs, 1H), 7.23 (d,J= 8 Hz, 2H),
7.02( d, J= 8 Hz, 2H), 6.28 (d, J= 8 Hz, 1H), 4.11 (m, 1H), 3.99 (m, 1H), 3.29 (s, 6H)5 2.45 (ddd, J} =
12 Hz, J2 = 8 Hz, J3 = 4 Hz, 1H), 2.25 (s, 3H), 1.85-1.65 (m, 11H), 1.58 (dt, Jx = 8 Hz, J2 = 4 Hz,
1H), 1.18(dt,7j= 8Hz,J2 = 4Hz, 1H)
Example 3254
Ar-{c/5-4-[(4,5-Dimethylpyrimidin-2-yl)amino]cyC1-5hexyl}-3,5-bis(trinuoromethyl)benzamide
trifluoroacetate
Step A: Synthesis of 2-chIoro-4,5~dimethylpyrimidine.

769
A mixture of 2, 4-dichloro-5-methylpyrimidine (0.3 g, 1.84 mmoi), AlMe3 (0.3 mL, 2.0M) and
Pd(PPh3)4 (85 mg, 4%mol) in dry THF (5 mL) was heated in a microwave synthesizer at 150 °C for 20
min. The solvent was removed in vacuo and the crude product subjected to chromatography (0-40 %
EtOAC/Hex) to yield 2-chIoro-4, 5-dimethyIpyrimidine (0.13 g, 50 %) as yellow solid.
ESI MS m/e: 143.1 M+¥f; 'HNMR (400 MHz, CDC13) 6 8.24 (s, 1H), 2.45 (s, 3H), 2.22 (s, 3H)
Step B: Synthesis of Ar-{m-4-[(4,5-dimethylpyrimidin-2-yI)amino]cyclohexyl}-3,5-
bis(trifluorom ethyl) benzam id e trifluoroacetate.
A mixture of 2-chloro-4, 5-dimethylpyrimidine (30 mg, 0.21 mmol), N-(cis-4-
aminocyclohexyl)-3,5-bis(trifluorornethyl)benzamide (74.6 mg, 0.21 mmol), Pd(OAc)2 (0.47 mg,
0.01 equiv.), dppf (1.16 mg, 0.01 equiv.) andKOtBu (59 mg, 0.53 mmol) in toluene (3 mL) was heated
in a microwave synthesizer at 150 °C for 20 min. The solvent was removed in vacuo and the crude
product subjected to purification by HPLC to give Ar-{c/5-4-[(4,5-dimethyl pyrimidin-2-
yl)amino]cyC1-5hexyl}-3,5-bis(trifluoromethyl)benzamide trifluoroacetate (25 mg, 21%) as yellow solid.
ESI MS m/e 461.2 M+JT; 'HNMR (400 MHz, CDC13) 5 8.36 (s, 3H), 7.99 (s, 1H), 4.47 (d, 1H), 4.23
(bs, 1H), 2.52 (s, 3H), 2.13 (s, 3H), 1.95-1.65 (m, 8H)
Example 3255
7V-(3,4-Difluorophenyl)-iV'-(m-4-{I4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)urea trifluoroacetate
Step A: Synthesis of Ar-(3,4-difluorophenyl)-7V'-(cw-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)urea trifluoroacetate.
c/i-A^^-Amino-cyclohexyO-S^A^-trimethyi-pyrimidine^^-diamine (30 mg, 0.12 mmol) was
dissolved in 1 mL of DMSO. l,2-Difluoro-4-isocyanato-benzene was added to the solution, and the

770
solution was stirred overnight. The crude was purified by HPLC to give JV-(3,4-difluoro phenyl)-JV-
(c/5-4-{[4-(dimethylamino)-5-methy]pyrimidin-2-yl]amino}cyC1-5hexyl)urea trifluoroacetate as a white
solid. (32.2 mg, 54.0%).
ESI MS m/e 405.3 (M + ¥t); lH NMR (400 MHz, CDCI3) 5 13.45 (s, 1H), 8.35 (d, J= 8.0 Hz, 1H),
7.67 (s, 1H), 7.52-7.47 (m, 1H), 7.28-7.26 (m, 1H), 7.07-6.99 (m, 2H), 4.00 (m, 1H), 3.96 (m, 1H),
3.32 (s, 6H), 2.27 (s, 3H), 1.78-1.67 (m, 8H).
Example 3256
2-[(3,4-Difluorophenyl)amino]-Ar-(c/s-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide
Step A: Synthesis of 2-[(3,4-difluorophenyl)amino]-Ar-(m-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyC1-5hexyl)nicotinamide.
3,4-Difluoro-aniIine (20.6 uL, 0.204 mmol) was dissolved in 1.0 mL of DMF. NaH (8.2 mg,
0.204 mmol) was added to the solution and allowed to stir for 10 minutes. 2-Chloro-Ar-[4-(4-
dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-nicotinamide (40 mg, 0.102 mmol) was
added and the mixture was stirred for another 5 minutes. The reaction was heated via Smith
Synthesizer at 200 °C for 1 hour. The crude was purified by silica column chromatography. The
column was flushed with 200 mL mixture methanol and methylene (1:9) and 100 mL of methanol to
give2-[(3,4-difluorophenyl)amino]-iV-(c/5-4-{[4-(dimethylamino)-5-methylpynmidin-2-
yl]amino}cyclohexyl)nicotinamide as a white solid. (30.0 mg, 61.2%)
ESI-MS m/z 482.5 (M + H*) ; 'H NMR (400 MHz, CDCI3) 5 8.32 (dd, J= 4.8, 1.6 Hz, 1H), 7.92-7.86
(m, 1H), 7.71 (dd, J= 7.6, J= 1.6 Hz, 1H), 7.64 (s, 1H), 7.19-7.03 (m, 2H), 6.76-6.73 (m, 1H), 6.34 (d,
J= 6.8 Hz, 1H), 4.95 (s, 1H), 4.11-4.03 (m, 2H),2.96 (s, 6H), 2.15 (s, 3H), 1.90-1.68 (m, 8H).

771
Example 3257
A^-(4-Chlorophenyl)-iV-(c/5-4-{[4-(dimethylamino)-5-methylpyrimidin-2-y1]amino}cyclohexyi)-iV-
ethylurea trifluoroacetate
Step A: Synthesis of ^-(^chlorophenyl^A^-^/y-^Jf^tdimethylamino^S-methylpyrimidin-l-
ylJaminoJcyclohexyO-A^-ethylurea trifluoroacetate.
c/5-A/2-(4-Amino-cyclohexyl)-5TA^fAr'-trimethyl-pyrimidine-2;4-diamine (75 mg, 0.30 mmol)
and IJ'-carbonyldiimidazole (58 mg, 0.36 mmol) were dissolved in 1 mL of methylene chloride in a
Smith Synthesizer vial and allowed to stir at room temperature overnight. To the vial, (4-chloro-
phenyl)-ethyl-amine (94 mg, 0.60 mmol) was added. The solution was heated via Smith Synthesizer at
130 °C for 30 minutes. The solvent was evaporated, and 1 mL of methanol was added to the crude to
redissolve it. The crude was then purified by HPLC to give yV-(4-chIorophenyi)-iV-(c/.s-4-{[4-
(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-Ar-ethylurea trifluoroacetate as a white
solid. (25.0 mg, 15%)
ESI MS m/e 431.3 (M + H+) ;'HNMR (400 MHz, CDC13) 5 14.0 (s, 1H), 8.65 (d, J= 6.4 Hz, 1H),
7.53 (dd, J= 9.2, J= 2.4 Hz, 2H), 7.43 (b, 1H), 7.28 (dd, J = 9.2, J= 2.4 Hz, 2H), 4.48 (bs, 1H), 4.16
(bs, 1H), 3.99 (m, 2H), 3.39 (s, 6H), 2.34 (s, 3H), 1.84-1.60 (m, 8H), 1.21 (t, J= 7.0 Hz, 3H).
Example 3258
Ar-(cis-4-{[5-Methyl-4-(methylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-{[2-
(trifluoromethyl)pyrimidin-4-yl]oxy}acetamide trifluoroacetate
Step A: Synthesis of resin bound N-methyl am in e.

772
2-(3,5 Dimethoxy-4-formyI)phenoxy ethyl polystyrene resin (1.0 gram; 0.90 mmol/gram) and
methylamine 2 M in methanol (5.85 mL, 11.7mmol) in 15 mL of CH2C12 was suspended in a fritted
synthesis flask. To this suspension was added a solution of NaBH(OAc)3 (.0117 mol) in CH2C12 (15
mL). After shaking the mixture overnight in a rotary shaker, the solution was removed by filtration.
The resulting resin bound N-methylamine was washed sequentially with CH2C12, DMF, and MeOH.
The washing sequence was repeated four times. The resin bound N-methylamine was dried under
vacuum for 20 minutes.
Step B: Synthesis of resin bound-4-(N-methyl-5 methyl- 2-chIoro)-pyrimidine.
The resin bound N-methylamine was suspended in DMF (10 mL). To the resin suspension was
added 2,4 dichloro-5-methyl-pyrimidine (1.35 mmol) followed by triethylamine (0.273 mL, 2.70
mmol). The reaction mixture was shaken overnight at room temperature. The solution was removed by
filtration and the resin washed sequentially with DMF, CH2C12 and MeOH. The wash sequence was
repeated four times. The resulting resin bound intermediate was dried under vacuum for 20 minutes..
Step C: Synthesis of resin bound c/s-N-(4-N-methyI-5 methyl-pyrimidyl-2yl)cyclohexane-l,4-
diamine.
The resin bound intermediate was divided up into three portions and each portion was
transferred into a 5 mL Smith synthesizer reaction vessel. The resins (0.272 mmol) were separately
suspended in anhydrous dioxane (3 mL). To each suspension was added cis 1,4 diamino cyclohexane
(0.405 mmol), tris(dibenzylidineacetone)dipalladium(O) (0.027 mol), 2,2 bisdiphenylphosphino-1,1
binapthyl (BINAP) ( 0.081mmol) and sodium tert-butoxide (1.35 mmol). The reactions were heated in
a microwave synthesizer at 140°C for 20 minutes. At the completion of the reaction, the resin
suspension was transferred to 8 mL fritted tubes. The solutions were removed by filtration. The resins
were sequentially washed with MeOH, H2O, MeOH, CH2C12, and MeOH. The washing sequence was
repeated three times. The resulting resin bound intermediate was dried under vacuum for 20 minutes.

773
Step D: Synthesis of c«-N-[4-(4-N-methyl-5 methyl-pyrimidyl-2yl-amino)-cyclohexyl]-
bromoacetamide.
The resin bound intermediate (0.27 mmol) was suspended in DC1-5 (3 mL). To the resin
suspension was added bromoacetyl bromide (0.27 mmol) and DIEA (.094 mL; 0.54 mmol). The
reaction was mixed in a rotary shaker for 45 minutes at room temperature- At the completion of the
reaction, the solution was removed by filtration. The resin was sequentially washed with DC1-5, DMF,
DC1-5, and MeOH. The washing sequence was repeated three times. The resulting resin bound
intermediate was dried under vacuum for 20 minutes.
Step E: Synthesis of Ar-(cis-4-{[5-methyl-4-(methyIamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-2-{[2-
(trifluoromethyI)pyrimidin-4-yl]oxy}acetamide trifluoro acetate.
The resin bound intermediate from Step D (0.27 mmol) was transferred into a 5 mL microwave
synthesizer vial. The resin was suspended in anhydrous DMF ( 2 mL). To the resin suspension was
added 4 hydroxy-2-trifluoromethyI pyrimidine (0.54 mmol) and potassium carbonate (0.54 mmol)
The reaction was heated in a microwave oven at 140 °C for 30 minutes. At the completion of the
reaction, the resin suspension was transferred to an 8 mL fritted tube. The solution was removed by
filtration and the resin washed sequentially with DMF, DC1-5, MeOH. The wash sequence repeated
three times.
After drying under vacuum for 20 minutes, the resin bound intermediate was treated with 5 mL
of TFA solution (TFA /CH2Cl2 /H20 20:20:1 v/v). The reaction was shaken for 2 hours and the TFA
solution was collected after filtration. The TFA was removed by rotary evaporation and the compound
subjected to purification by preparative HPLC to give Ar-(cis-4-{[5-methyl-4-(methylamino)pyrimidin-
2-yl]amino}cyclohexyl)-2-{[2-(trifluoromethyl)pyrimidin-4-yl]oxy}acetamide trifluoroacetate (2.1 mg.
5%) as a white solid.

774
ESI MS m/e 440.3 M+H4"; *H NMR (400MHz, CD3OD) 8 (ppm): 8.69 (m, 1H), 7.45 (m, 1H), 7.21-
7.17 (m, 1H), 4.95 (m, 2H), 4.03 (bs, 1H), 3.82 (bs, 1H), 3.04 (s, 3H), 1.98 (s, 3H), 1.93-1.61 (m, 8H).
Example 3259
2,2-Difluoro-Ar-(c«-4-{[4-methyl-6-(methyIamino)pyrimidin-2-yl]amino}cyclohexyl)-lr3-
benzodioxole-5-carboxamide trifluoroacetate
Step A: Synthesis of resin bound N-methylamine.
2-(3,5 Dimethoxy-4-formyl)phenoxy ethyl polystyrene resin (1.0 gram; 0.94mmol/gram) and
methylamine (0.0122 mol) in 15 mL of CH?C12 was suspended in a fritted synthesis flask. To this
suspension was added a solution of NaBH(OAC)3 (0.0122 mol) in CH2CI2 (15 mL). After shaking the
mixture overnight in a rotary shaker, the solution was removed by filtration. The resulting resin bound
N-methylamine was washed sequentially with CH2C12, DMF, and MeOH. The washing sequence was
repeated four times. The resin bound N-methylamine was dried under vacuum for 20 minutes.
Step B: Synthesis of resin bound-4-(N-methyl-6 methyl- 2-chIoro)-pyrimidine.
The resin bound N-methylamine was suspended in DMF (10 mL). To the resin suspension was
added 2,4 dichloro-6-methyl-pyrimidine (1.41 mmol) followed by triethylamine (0.393 mL, 2.82
mmol). The reaction mixture was shaken at 40 °C overnight. The solution was removed by filtration
and the resin washed sequentially with DMF, CH2C12 and MeOH. The wash sequence was repeated
four times. The resulting resin bound intermediate was dried under vacuum for 20 minutes.
Step C: Synthesis of resin bound c/s-N-(4-N-methyl-6methyl-pyrimidyl-2yl)cyclohexane-
1,4-diamine.

775
The resin bound intermediate was divided up into three portions and each portion was
transferred into a 5 mL Smith synthesizer reaction vessel. The resins (0.282 mmol) were separately
suspended in a 1:1 solution of IPA/H20 (3 mL). To each suspension was added cis 1,4 diamino
cyclohexane (0.85 mmol) and DIEA (0.295ml; 1.69 mmol). The reactions were heated in a microwave
synthesizer at 180°C for 4.5 hours. The resins were pooled together; and the solution removed by
filtration. The resin was sequentially washed with IPA, H20, MeOH, CH2CI2, and MeOH. The washing
sequence was repeated three times. The resulting resin bound intermediate was dried under vacuum for
20 minutes.
Step D: Synthesis of 2^-difluoro-Ar-(c«p-4-{[4-methyl-6-(methyIamino)pyrimidin-2-
yl]amino}cyclohexyl)-l,3-beiizodioxole-5-carboxamide trifluoroacetate.
The resin bound intermediate was suspended in DMF (8mL). To the resin suspension was
added the 2,2 diflouro 1,3 benzodioxole 5- carbonyl chloride (0.846 mmol) and triethylamine ( 0.256
mL; 1.69 mmol). The reaction was shaken in a rotary mixer at room temperature for 45 minutes. The
solution was removed by filtration and the resin washed sequentially with DMF, CH2CI2, MeOH. The
wash sequence repeated three times.
After drying under vacuum for 20 minutes, the resin bound intermediate was treated with 15
mL of TFA solution (TFA /CH2C12 /H20 20:20:1 v/v). The reaction was shaken for 2 hours and the
TFA solution was collected after filtration. The TFA was removed by rotary evaporation and the
compound subjected to purification by preparative HPLC to give 2,2-difluoro-Ar-(cw-4-{[4-methyl-6-
(methylamino)pyrimidin-2-yl]amino}cyclohexyl)-l)3-benzodioxole-5-carboxamide trifluoroacetate
(2.0 mg. 2%) as a white solid.
ESI MS m/e 420.5 M+H*; 'HNMR (400MHZ, CD3OD) 5 (ppm): 8.24 (m, 1H), 7.72-7.68 (m, 2H),
7.31-7.29 (m, 1H), 5.86 (s, 1H), 4.18-3.99 (m, 2H), 2.99 (s, 3H), 2.25 (s, 3H), 1.93-1.80 (m, 8H).

776
Examples 3260-3262
Compounds 3260 to 3262 were prepared in a similar manner as described in Example 3242
using the appropriate bromoacetophemone and amine intermediate from Step A.
Examples 3263-3267
Compounds 3263 to 3267 were prepared in a similar manner as described in Example 3243
using the appropriate acid and amine intermediate from Step A.
Examples 3268-3272
Compounds 3268 to 3272 were prepared in a similar manner as described in Example 3244
using the appropriate isocyanate and amine intermediate from Step A.
Examples 3273-3275
Compounds 3723 to 3275 were prepared in a similar manner as described in Example 3245
using the appropriate amine and carboxylic intermediate from Step A.
Examples 3276-3280
Compounds 3276 to 3280 were prepared in a similar manner as described in Example 3246
using the appropriate acid chloride and amine intermediate from Step D.
Examples 3281-3291
Compounds 3281 to 3291 were prepared in a similar manner as described in Example 2656
using the appropriate thioderivative and amine intermediate from Step A.
Examples 3292-3303

777
Compounds 3292 to 3303 were prepared in a similar manner as described in Example 3251
using the appropriate amine and carboxylic intermediate from Step B.
Examples 3304-3307
Compounds 3304 to 3307 were prepared in a similar manner as described in Example 3252
using the appropriate amine and carboxylic intermediate from Step B.
Examples 3308
Compounds 3308 were prepared in a similar manner as described in Example 3251 using the
appropriate amine and carboxylic intermediate from Step B.
Examples 3309-3315
Compounds 3309 to 3315 were prepared in a similar manner as described in Example 3252
using the appropriate amine and carboxylic intermediate from Step B.
Examples 3316-3320
Compounds 3316 to 3320 were prepared in a similar manner as described in Example 3253
using the appropriate aldehyde and amine intermediate from Step D.
Examples 3321-3345
Compounds 3321 to 3345 were prepared in a similar manner as described in Example 3255
using the appropriate isocyate and amine intermediate from Step A.
Examples 3346-3355
Compounds 3346 to 3355 were prepared in a similar manner as described in Example 3257
using the appropriate aniline and amine intermediate from Step A.

778
Examples 3356-3357
Compounds 3356 to 3357 were prepared in a similar manner as described in Example 2638
using the appropriate hydroxyaryl derivative and bromide intermediate from Step B.
Examples 3358-3359
Compounds 3358 to 3359 were prepared in a similar manner as described in Example 3259
using the appropriate acid chloride and amine intermediate from Step D.
Examples 3360-3365
Compounds 3360 to 3365 were prepared in a similar manner as described in Example 3259
using the appropriate hydroxyaryl derivative and bromide intermediate from Step E.
Examples 3366-3367
Compounds 3366 to 3367 were prepared in a similar manner as described in Example 3250
using the appropriate acid chloride derivative and amine intermediate from Step E.
Examples 3368-3381
Compounds 3368 to 3381 were prepared in a similar manner as described in Example 3249
using the appropriate thiophenol and nicotinamide intermediate from Step A.
Example 3382
Compound 3382 was prepared in a similar manner as described in Example 2497 using 4-
trifluoromethoxy-benzoyl chloride and the amine intermediate from Step E.

779

Ex. No. compound name MS class
3260 1 -(4-chlorophenyl)-2-[(cis-4- {[4-(dimethylamino)-5-
methyIpyrimidin-2-yl]amino}cyclohexyl)amino]ethanone 402.4 (M + H) 2
3261 l-(3,4-difluorophenyl)-2-[(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)aminolethanone 404.4 (M + H) 3
3262 l-(4-bromophenyl)-2-[(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yllamino}cyclohexyl)amino]ethanone 446.3 (M + H) 3
3263 N-{l-[3,5-bis(trifluoromethyl)phenyl]-l-methylethyl}-N'-(cis-4-
{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino} -
cyclohexyl)urea 547.6 (M + H) 2
3264 N-[l-t4-chIorophenyl)-l-methylethyI]-N'-(cis-4-{[4-
(dimethylamino)-5-methylpyrimidin-2-ynamino}cyC1-5hexyl)urea 445.3 (M + H) 1
3265 N-[l-(4-chlorophenyl)-l-methylethyl]-N'-(cis-4-{[4-
(dimethylatnino)-6-methylpyrimidin-2-yl]amino}cyclohexyi)urea 445.2 (M + H) 2
3266 N-[l-(4-chlorophenyl)cyclopropyl]-N'-(cis-4-{[4-
(dimethylamino)-5-methvlpyrimidin-2-yllamino}cyclohexvl)urea 443.3 (M + H) 1
3267 N-[l-(4-chlorophenyl)cyclopropyl]-N'-(cis-4-{[4-
(dimethylamino)-6-methylpyrimidin-2-vllamino}cyc!ohexyl)urea 443.4 (M + H) 1
3268 N-{l-[3,5-bis(trifluoromethyl)phenyl]-l-methylethyl}-N'-(cis-4-
{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-
N-methylurea 561.4 (M + H) 3
3269 N-[l-(4-chlorophenyl)-l-methylethyl]-N'-(cis-4-{[4-
(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-
methylurea 459.6 (M + H) 1
3270 N-[ 1 -(4-chlorophenyl)-1 -methyIethyl]-N'-(cis-4- {[4-
(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)'N-
methyiurea 459.5 (M + H) 2
3271 N-[ 1 -(4-chlorophenyl)cyC1-5propy l]-N'-(cis-4-{ [4-
(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyI)-N-
methylurea 457.5 (M + H) 2
3272 N-[ 1 -(4-chlorophenyl)cyclopropyI]-N'-(cis-4- {[4-
(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-N-
methylurea 457.2 (M + H) 3
3273 cis-N-[l-(4-chlorophenyl)-l-methylethyl]-4-{[4-(dimethylamino)-
5-methylpyrimidin-2-yl]amino}cyclohexanecarboxamide 430.3 (M + H) 2
3274 cis-N-[ 1 -(4-chlorophenyl)-1 -methylethyl]-4- {[4-(dimethy lamino)-
6-methylpyrimidin-2-yIlamino}cyC1-5hexanecarboxamide 430.4 (M + H) -i
3275 cis-N-{l-[3,5-bis(trifluoromethyl)phenyl]-l-methylethyl}-4-{[4-
(dimethylamino)-6-methylpyrimidin-2-
vllaminojcyclohexanecarboxamide 532.3 (M + H) 3
3276 4-chloro-N-{cis-4-[(4-methoxy-5-methylpyrimidin-2-
yl)aminolcyclohexyl}benzamide 375.1 (M + H) -i
3277 N-{cis-4-[(4-methoxy-5-methylpyrimidin-2-
yl)aminolcyclohexyl}-4-(trifluoromethoxy)benzamide 425.1 (M + H) 3
3278 3,4'dichloro-N-{cis-4-[(4-methoxy-5-methylpyrimidin-2-
yl)aminolcyclohexyl}benzamide 408.9 (M + H) 2
3279 3,5-dichloro-N-{cis-4-[(4-methoxy-5-rnethylpyrimidin-2-
yl)amino]cyclohexvl}ben2amide 409.1 (M + H) 3

780

Ex. No. compound name MS class
3280 N-{cis-4-[(4-methoxy-5-methylpyrimidin-2-
yl)aminolcyclohexvl}-3,5-bis(trifluoromethyl)benzamide 477.2 (M + H) 3
3281 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexvl)-2-[(4-fluorophenyl)sulfonyllnicotinamide 513.4(M + H) 1
3282 2-[(4-chIorophenyl)sulfonyl]-N-(cis-4-{[4-(dimethylamino)-5-
methylpvrimidin-2-yllamino}cvclohexyl)nicotinamide 529.4 (M + H) 1
3283 2-[(3-chlorophenyl)sulfonyl]-N-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yI]amino}cyclohexyl)nicotinamide 529.4 (M + H) 2
3284 2-[(2-chloropheny l)sulfonyl]-N-(cis-4- {[4-(dimethylamino)-5-
methylpyrimidin-2-vl]amino}cyclohexyl)nicotinamide 529.3 (M + H) 2
3285 2-[(3-bromophenyl)sulfonyl]-N-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-vl1amino}cyclohexyl)nicotinamide 573.6 (M + H) 2
3286 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-[(4-methoxyphenyI)sulfonyl]-
nicotinamide 525.4 (M + H)
3287 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-{[3-(trifluoromethyl)phenyl]sulfonyl}-
nicotinamide 563.5 (M + H) 2
3288 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cvclohexyl)-24(4-methylphenyl)sulfonyllnicotinamide 509.6 (M + H) 2
3289 2-[(4-bromophenyl)sulfonyl]-N-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-vllamino}cyclohexyl)nicotinamide 573.5 (M + H) 2
3290 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
vllamino}cyclohexvl)-2-f(2-methvl-3-furvl)sulfonyllnicotinaniide 499.4 (M + H) -i
3291 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-{[4-(trifluoromethyl)phenyI]sulfonyl}-
nicotinamide 563.5 (M + H) 2
3292 cis-N-[( 1 S)-l -(4-chlorophenyl)ethy l]-4- {[4-(dimethy lamino)-5-
methylpyrimidin-2-yllamino}cyclohexanecarboxamide 416.3 (M + H) 2
3293 cis-N-{(lS)-l-[3,5-bis(trifIuoromethyl)phenyl]ethyl}-4-{[4-
(dimethylamino)-5-methyIpyrimidin-2-
vllaminojcyclohexanecarboxamide 518.4 (M + H) 3
3294 cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino} -N-
r(lR)-l-(2-fluorophenyl)ethyllcyclohexanecarboxamide 400.3 (M + H) 3
3295 cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-
[(1S)-1 -(2-fluorophenyl)ethyllcyclohexanecarboxamide 400.3 (M + H)
3296 cis-N-[( 1S)-1 -(4-bromopheny l)ethyl]-4-{ [4-(dimethylamino>5-
methylpyrimidin-2-yl]amino}cyclohexanecarboxamide 460.3 (M + H) 1
3297 cis-N-[(lR)-l-(4-bromophenyl)ethyl]-4-{[4-(dimethylamino>5-
methylpyrimidin-2-yllamino}cyclohexanecarboxamide 460.3 (M + H) 2
3298 4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-{(lS)-
l-[3-(trifluoromethyl)phenyIlethyl}cyclohexanecarboxamide 450.2 (M + H) 1
3299 4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-{(lR)-
l-[3-(trifluoromethyl)phenyllethyl}cyclohexanecarboxamide 450.3 (M + H) 1
3300 4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-{(lS)-
l-[2-(trifluoromethyl)phenyl]ethyl}cyclohexanecarboxamide 450.4 (M + H) 1
3301 4- {[4-(dimethy lamino)-5-methylpyrimidin-2-y I]amino} -N- {(1R)-
l-[2-(trifluoromethyl)phenyl]ethyl}cyclohexanecarboxamide 450 (M + H) 3

781

Ex. No. compound name MS class
3302 cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
N- {(1S)-1 -[4-(trifluoromethoxy)phenyl]ethy 1} -
cyclohexanecarboxamide 466.4 (M + H) 1
3303 cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-
N-{( 1R)-1 -[4-(trifluoromethoxy)pheny ljethyl} -
cyclohexanecarboxamide 466.4 (M + H) 2
3304 cis-N-[( 1S)-1 -(4-bromophenyl)ethyl]-4-[(4-methylquinolin-2-
yl)amino"|cyclohexanecarboxamide 466.4 (M + H) 3
3305 cis-N-[(lR)-l-(4-chlorophenyl)ethyI]-4-[{4-methylquinolin-2-
yl)ami no] cyclohexanecarboxamide 422.3 (M + H) 2
3306 cis-N-[(lS)-l-(4-chlorophenyl)ethyl]-4-[(4-methylquinolin-2-
yl)amino]cyclohexanecarboxamide 422.4 (M + H) 2
3307 cis-4-[(4-methylquinolin-2-yl)amino]-N-{(lR)-l-[3-
(trifluoromethyl)phenyllethyl} cyclohexanecarboxamide 456.3 (M + H) 1
3308 cis-N-[(lS)-l-(4-bromophenyl)ethyl]-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yllamino}cyclohexanecarboxamide 460 (M + H) 1
3309 cis-N-{(lS)-l-[3,5-bis(trifluoromethyl)phenyl]ethyl}-4-[(4-
methylquinolin-2-yl)aminolcyclohexanecarboxamide 524.2 (M + H) 2
3310 cis-4-[(4-methyIquinolm-2-yl)amino]-N-{(lR)-l-[4-
(trifluoromethoxy)phenyl]ethyl} cyclohexanecarboxamide 472.4 (M + H)
3311 cis-N-[( 1R)-1 -(2-fluorophenyl)ethyl]-4-[(4-methylquinolin-2-
yl)amino]cyclohexanecarboxamide 406.2 (M + H) 3
3312 cis-N-[( 1S)-1 -(2-fluorophenyl)ethyl]-4-[(4-methyIquinolin-2-
yl)amino]cyclohexanecarboxamide 406.3 (M + H) 1
3313 cis-4-[(4-methylquinolin-2-yl)amino]-N-{(lR)-l-[2-
(trifluoromethyl)phenyl]ethyl}cyclohexanecarboxamide 456.2 (M + H) 2
3314 cis-4-[(4-methylquinolin-2-yl)amino]-N-{( 1S)-1 -[2-
(trifluoromethyl)phenyll ethyl} cyclohexanecarboxamide 456.3 (M + H) 1
3315 cis-4-[(4-methylquinolin-2-yi)amino]-N- {(1S)-1 -[3-
(trifluoromethyl)phenyl]ethyl}cyclohexanecarboxamide 456 (M + H) 1
3316 trans -2-(4-chlorophenyl)-N-(cis-4-{ [4-(dimethylamino)-5-
methylpyrimidin-2-yI]amino}cyclohexyl)-
cyclopropanecarboxamide 428.4 (M + H) 1
3317 rra«5-2-(3-chlorophenyl)-N-(cis-4-{[4'(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)-
cyclopropanecarboxamide 428 (M + H) 1
3318 /ri3«5-2-(3,4-difluorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-
methy!pyrimidin-2-yl]amino}cyC1-5hexyl)-
cyclopropanecarboxamide 430.2 (M + H) 1
3319 /m«5-2-(3,4-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)-
cyclopropanecarboxamide 462.3 (M + H) 1
3320 rraw-2-[3,5-bis(trifluoromethyl)phenyl]-N-(cis-4-{[4-
(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-
cyclopropanecarboxamide 530.2 (M + H) 1
3321 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)-Nl-(2-methoxyphenyl)urea 399.3 (M + H) 2

782

Ex. No. compound name MS class
3322 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyl)-N'-{3-methoxyphenyl)urea 399.3 (M + H) ■■>
3323 N-(3,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yI]amino}cyclohexyl)urea 429.4 (M + H) 1
3324 N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yl]amino)cyclohexyl)-N'-(2-fluorophenyl)urea 387.5 (M + H) 2
3325 N-(cis-4- {[4-(dimethylamino)-5-methy lpyrimidin-2-
yllamino}cyclohexyl)-N'-(3-fluorophenyl)urea 387.4 (M + H) 2
3326 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
ynamino}cyclohexyl)-N'-(4-fluorophenyl)urea 387.4 (M + H) 1
3327 N-(3,4-difluorophenyl)-N'-(cis-4-{[4-(dimethyIamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)urea 405.3 (M + H) 2
3328 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyC1-5hexyl)-N'43-(trifluoromethyl)phenyl]urea 437.3 (M + H)
3329 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyl)-N'-[4-(trifluoromethyI)phenyllurea 437.2 (M + H)
3330 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
ynamino}cyclohexyl)-N'-[2-(trifluoromethoxy)phenyl]urea 453.1 (M + H) 1
3331 N-(3-chloro-4-fluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-
methvlpyrimidin-2-yllamino}cyclohexyl)urea 421.1 (M + H) 2
3332 N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)-N'-[4-fluoro-3-(trifluoromethyl)-
phenyl]urea 455.3 (M + H)
3333 N-(4-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yIlamino}cyclohexyl)urea 403.2 (M + H) 2
3334 N-[355-bis(trifluoromethyl)phenyl]-N'-(cis-4-{[4-
(dimethylamino)-5-methy]pyrimidin-2-yl]amino}cyC1-5hexyl)urea 505.3 (M + H) 2
3335 N-(4-bromophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)urea 447.1 (M + H) 1
3336 N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yllamino}cyclohexyI)-N'-(2-methylphenyl)urea 383.2 (M + H) 2
3337 N-(3,4-dichlorophenyl)-N'-(cis-4-{[4-(dimethyIamino)-5-
methylpyrimidin-2-yIlamino}cyclohexy!)urea 437.3 (M + H) 2
3338 N-(2,4-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yllamino}cyclohexyl)urea 437.3 (M + H) 2
3339 N-(3,5-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yllamino}cyclohexyl)urea 437.3 (M + H) 2
3340 N-(3-chlorophenyl)-N'-(cis-4- {[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyI)urea 403.4 (M + H)
3341 N-benzyI-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino} eye lohexyl) urea 383.5 (M + H) 2
3342 N-(2,5-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yllamino}cyclohexyl)urea 437.3 (M + H) 2
3343 N-(2,3-dichlorophenyl)-Nl-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)urea 437.3 (M + H) 3
3344 N-[2-chloro-6-(trifluoromethyl)phenyI]-N'-(cis-4-{[4-
(dimethylamino)-5-methYlpyrimidin-2-yllamino}cyclohexyl)urea 471.3 (M + H) 3

783

Ex. No. compound name MS class
3345 N-(cis-4- {[4-(dimethy lamino)-5-methy lpyrimidin-2-
yl]amino}cyC1-5hexyl)-N'-(2,4,6-trichlorophenyl)urea 471.3 (M + H) 1
3346 N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyC1-5hexyl)-N-(2-fluorophenyl)-N-methylurea 401.2 (M + H) 3
3347 N-(2-chlorophenyl)-N'-(ds-4- {[4-(dimethylamino)-5-
methyipyrimidin-2-yllamino}cyclohexyl)-N-methylurea 417.1 (M + H) 2
3348 N-(2,4-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yllamino}cyclohexyl)-N-methylurea 451.2 (M + H) 1
3349 N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyI)-N-ethyl~N-[2-(trifluoromethoxy)-
phenyllurea 481.3 (M + H) 2
3350 Nt-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yllamino}cyclohexyl)-N-ethyl-N-phenylurea 397.1 (M + H) 1
3351 N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-N-ethyl-N-[4-(trifluoromethoxy)-
phenyl]urea 481.1 (M + H) 1
3352 N'-(cis-4- {[4-(dimethylamino)~5-methylpyrimidin-2-
yl]amino}cyclohexyl)-N-methyl-N-[2-(trifluoromethoxy)-
phenyllurea 467.2 (M + H) 1
3353 N-(4-chlorophenyl)-N'-(cis-4- {[4-(dimethy lamino)-5-
methylpyrimidin-2-yllamino}cyclohexyl)-N-ethyIurea 431.3 (M + H) 1
3354 N-[3,5-bis(trifIuoromethyl)phenyl]-N'-(cis-4-{[4-
(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-
ethylurea 533.1 (M + H) 1
3355 N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyI)-N-ethyUN-(3-methylphenyl)urea 411.3 (M + H) 1
3356 N-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyI)-2-{[l-methyl-3-(trifluoromethyl)-lH-
pyrazol-5-yl]oxy}acetamide 456.4 (M + H) 1
3357 N-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-{[6-(trifluoromethyl)pyrimidin-4-
yl]oxy) acetamide 454.2 (M + H) 3
3358 2,2-difluoro-N-(cis-4-{[4-methyl-6-(methylamino)pyrimidin-2-
yllamino)cyclohexyI)-l,3-benzodioxole-5-carboxamide 420.5 (M + H)
3359 4-chloro-N-(cis-4-{[4-methyl-6-(methylamino)pyrimidin-2-
yl]amino}cyclohexyl)-3-(trifluoromethyl)benzamide 442.1 (M + H)
3360 2-(3,4-dichlorophenoxy)-N-(cis-4-{[4-methyl-6-
(methylamino)pyrimidin-2-yllamino}cyclohexyl)acetamide 438.3 (M + H) 1
3361 N-(cis-4- {[5-methyl-4-(methylamino)pyrimidin-2-yl]amino} -
cyclohexyl)-2-{[2-(trifluoromethyl)pyrimidin-4-yl]oxy}-
acetamide 440.3 (M + H)
3362 N-(cis-4-{[5-methyl-4-(methylamino)pyrimidin-2-yl]amino}-
cyclohexy l)-2- {[ 1 -methyl-3-(trifluoromethyl)-1 H-pyrazol-5-
yl]oxy}acetamide 442.5 (M + H) 3
JJOJ N-(cis-4- {[5-methyl-4-(methylamino)pyrimidin-2-yl]amino} -
cyclohexyl)-2-{[6-(trifIuoromethyl)pyrimidin-4-ylloxy}acetamide 440.3 (M + H)

784

Ex. No. compound name MS class
3364 N-(cis-4-{[5-methyl-4-(methylamino)pyrimidin-2-yl]amino}-
cyclohexyI)-2- {[ 1 -methyl-5-(trifluoromethyl)-1 H-pyrazoi-3-
yl]oxy}acetamide 442.4 (M + H)
3365 N-(cis-4-{[5-methyl-4-(methylamino)pyrimidin-2-yl]amino}-
cyclohexyl)-2-{[3-(trifluoromethyl)-lH-pyrazol-5-yl]oxy}-
acetamide 428.2 (M + H)
3366 3,4-difluoro-N-(cis-4-{[(4-methylquinolin-2-
yl)methyllamino}cyclohexyl)benzamide 410.3 (M + H)
3367 3-chloro-N-(cis-4-{[(4-methylquinoIin-2-
yl)methy]]amino}cyclohexyl)benzamide 408.3 (M + H)
3368 N-(cis-4- {[4-(dimethy lamino)-6-methy lpyrimidin-2-
yl]amino}cvclohexyI)-2-[(4-fluorophenyI)sulfonyllnicotinamide 513.5 (M + H) 2
3369 2-[(2-chlorophenyl)sulfonyl]-N-(cis-4-{[4-(dimethylamino)-6-
methyIpyrimidin-2-yl]amino}cyclohexyl)nicotinamide 513.5 (M + H) 2
3370 2-[(3-chlorophenyl)sulfonyl]-N-(cis-4-{[4-(dimethylamino)-6-
methylpvrimidin-2-y!lamino}cyclohexyl)nicotinamide 529.1 (M + H) 2
3371 2-[(4-chlorophenyl)sulfonyl]-N-(cis-4-{[4-(dimemylamino)-6-
methylpyrimidin-2-yllamino}cyclohexyI)nicotin amide 529.1 (M + H) ^
3372 2-[(2-bromophenyl)sulfonyI]-N-(cis-4- {[4 -(dimethyl amino)-6-
methylpyrimidin-2-yl]amino}cyclohexyl)nicotinamide 573.3 (M + H) 3
3373 2-[(3-bromophenyl)suifonyl]-N-(cis-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yllamino}cyclohexyI)nicotinamide 575.4 (M + H) 2
3374 2-[(4-bromophenyl)sulfonyl]-N-(cis-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yl]amino}cyclohexyl)nicotinamide 573.2 (M + H)
3375 N-(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}cyC1-5hexyl)-2-f(2-methylphenyi)sulfonyl]nicotinamide 509.5 (M + H) 2
3376 N-(cis-4- {[4-( dimethyl ami no)-6-methyIpyrim id in-2-
yllamino}cyclohexyl)-2-[(3-methylphenyl)sulfonyllnicotinamide 509.5 (M + H) 3
3377 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yllamino}cyclohexyl)-2-f'(4-methylphenyl)sulfonyl]nicotinamide 509.5 (M + H) 2
3378 N-(cis-4- {[4~(dimethylamino)-6-methylpyrimtdin-2-
yl]amino}cyclohexyl)-2-[(2-methoxyphenyl)sulfonyl]-
nicotinamide 525.3 (M + H) 3
3379 N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-[(3-methoxyphenyl)sulfonyl]-
nicotinamide 525.3 (M + H) 3
3380 N-(cis-4- {[4-(dimethy lamino)-6-methylpyrimidin-2-
y!]amino}cyclohexyl)-2-[(4-methoxyphenyl)sulfonyl]-
nicotinamide 525.3 (M + H) 3
3381 N-(cis-4- {[4-(dimethy lamino)-6-methylpyrimidin-2-
yI]amino}cyclohexyl)-2-{[2-(trifluoromethyl)phenyl]-
sulfonyljnicotinamide 563.4 (M + H) 3
3382 N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}-4-
(trifluoromethoxy)benzamide 444.4 (M + H) 1

785
Example 3383
4-Chloro-Ar-[cw-4-(4-dimethylamino-6-methyI-pyrimidin-2-ylamino)-cyC1-5hexyli-3-
fluoro-benzamide hydrochloride
Step A: Synthesis of 4-chloro-Ar-[cw-4-(4-dimethylamino-6-methyl-pyrimidin-2-
ylamino)-cyclohexyl]-3-fluoro-benzamide hydrochloride.
To a solution of Ar2-{c/5-4-amino-cyclohexyl)-6^V/;Ar'-trimethyI-pyrimidine-2,4-diamine
obtained in step A of example 3127 (300 mg) in DMF (3 mL) were added 4-chloro-3-fluoro-benzoic
acid (252 mg), Et3N (0.42 mL), HOBt-H2O (276 mg), and EDC-HC1 (277 mg). The reaction mixture
was stirred at ambient temperature for 1 day. The reaction mixture was poured into saturated aqueous
NaHCO3 and the aqueous layer was extracted with CHC13 (three times). The combined organic layer
was dried over MgSOj, filtered, concentrated under reduced pressure, and purified by medium-
pressure liquid chromatography (NH-silica gel, 15% to 60% EtOAc in hexane). The solution of the
above purified material in EtOAc (5 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). The
mixture was stirred at ambient temperature for 1 hr and concentrated. The residue was suspended in
Et2O (20 mL) and the suspension was stirred at ambient temperature for 2 hr. The precipitate was
collected by filtration, washed with Et2O, and dried at 80 °C under reduced pressure to give
4-chloro-Ar-[cw-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-cyclohexyl]-3-fluoro-
benzamide hydrochloride (335 mg) as a white solid.
ESI MS m/e 406, M (free) + it; 'HNMR (300 MHz, CDC13) 5 1.64-2.01 (m, 8 H), 2.35 (s, 3 H), 3.14
(s, 3 H), 3.26 (s, 3 H), 4.02-4.31 (m, 2 H), 5.74 (s, 1 H), 6.84-6.96 (m, 1 H), 7.40-7.49 (m, 1 H),
7.53-7.60 (m, 1 H), 7.69 (dd, J = 9.7, 1.9 Hz, 1 H), 8.48-8.65 (m, 1 H), 12.93-13.08 (m, 1 H).
Example 3384
3-Chloro-7V-[cw-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-cyclohexyl]-5-
fluoro-benzamide hydrochloride

786
Step A: Synthesis of 3-chloro-iV-[c/s-4-(4-dimethylamino-6-inethyl-pyrimidin-2-ylamino)-
cyclohexyl]-5-fluoro-benzamide hydrochloride.
Using the procedure for the step A of example 3383, the title compound was obtained.
ESI MS m/e 406, M (free) + H+; 'H NMR (300 MHz, CDC13) 5 1.64-2.05 (m, 8 H), 2.36 (s, 3 H), 3.15
(s, 3 H), 3.26 (s, 3 H), 4.01-4.30 (m, 2 H), 5.75 (s, 1 H), 6.45-6.54 (m, 1 H), 7.17-7.23 (m, 1 H),
7.40-7.47 (m, 1 H), 7.57-7.61 (m, 1 H), 8.60-8.71 (m, 1 H), 13.07-13.19 (m, I H).
Example 3385
Ar-[c«-4-(4-Dimethylamino-6-methyl-pyrimidin-2-ylamino)-cyclohexyl]-3,4,5-trifluoro-
benzamide hydrochloride
Step A: Synthesis of AT-[cw-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
3,4,5-trifluoro-benzamide hydrochloride.
Using the procedure for the step A of example 3383, the title compound was obtained.
ESI MS m/e 408, M (free) + H+; ]H NMR (300 MHz, CDC13) 5 1.62-2.01 (m, 8 H), 2.36 (s, 3 H), 3.14
(s, 3 H), 3.26 (s, 3 H), 4.00-4.32 (m, 2 H), 5.75 (s, 1 H), 6.70-6.81 (m, 1 H), 7.47-7.59 (m, 2 H),
8.54-8.66 (m, 1 H), 12.92-13.08 (m, 1 H).
Example 3386
3-Chloro-4-fluoro-Ar-[cw-4-(5-methyl-4-methylamino-pyrimidin-2-ylamino)-cyclohexyl]-
benzamide hydrochloride
Step A: Synthesis of (2-chloro-5-methyl-pyrimidin-4-yl)-methyl-amine.
To the solution of 2,4-dichloro-5-methylpyrimidine (5.00 g) in THF (50 mL) were added
iPr2NEt (6.4 mL) and 40% aqueous MeNH2 (4.78 mL). The mixture was stirred at ambient
temperature for 12 hr and concentrated under reduced pressure. To the residue was added saturated

787
aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (three times). The combined
organic layer was dried over MgSO4, filtered, concentrated, and purified by medium-pressure liquid
chromatography (NH-silica gel, 9% to 20% EtOAc in hexane) to give (2-chloro-5-methyl-pyrimidin-
4-yl)-methyl-amine (3.55 g) as a white solid.
ESI MS m/e 408, M + H+; !H NMR (300 MHz, CDCI3) 5 2.01 (d, J= 0.8 Hz, 3 H), 3.07 (d, J= 5.0
Hz, 3 H), 4.89-5.06 (m, 1 H), 7.79 (s, 1 H).
Step B: Synthesis of 3-chloro-4-fluoro-7V-[c«-4-(5-methyl-4-methylamino-pyrimidin-2-
ylamino)-cyclohexyl]-benzamide hydrochloride.
Using the procedure for the step B of example 3228, the title compound was obtained.
ESI MS m/e 392, M (free) + H-, lH NMR (300 MHz, DMSO-d6) 5 1.64-1.98 (m, 11 H), 2.94 (d, J =
4.5 Hz, 3 H), 3.80-4.08 (m, 2 H), 7.48-7.67 (m, 2 H), 7.87-7.95 (m, 1 H), 8.08-8.51 (m, 4 H),
11.95-12.03 (m, 1 H).
Example 3387
4-Chloro-Af-[c/s-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-3-fluoro-
benzamide hydrochloride
Step A: Synthesis of 4-chloro-iV-[c/s-4-(4-dimethylamino-5-methyI-pyrimidin-2-ylamino)-
cyC1-5hexylI-3-fluoro-benzamide hydrochloride.
To a solution of ^-(c/M-amino-cyclohexy^-S^/^-trimethyl-pyrimidine-
2,4-diamine obtained in step C of example 3119 (250 mg) in DMF (4 mL) were added
4-chloro-3-fluoro-benzoic acid (209 mg), Et3N (0.36 mL), HOBt-H2O (230 mg), and EDC-HC1 (230
mg). The reaction mixture was stirred at ambient temperature for 16 hr. The reaction mixture was
poured into saturated aqueous NaHCO3 and the aqueous layer was extracted with CHCI3 (three times).
The combined organic layer was dried over MgSO4, filtered, concentrated under reduced pressure,
and purified by medium-pressure liquid chromatography (NH-silica gel, 20% to 40% EtOAc in

788
hexane). The solution of the above purified material in EtOAc (10 mL) was added 4 M hydrogen
chloride in EtOAc (0.5 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated.
The residue was suspended in Et2O (10 mL) and the suspension was stirred at ambient temperature
for 4 hr. The precipitate was collected by filtration, washed with Et2O, and dried at 80 °C under
reduced pressure to give 4-chloro-Af-[c/s-4-(4-dimethylamino-5-methyl-pyrirnidin-2-
ylamino)-cyclohexyl]-3-fluoro-benzamide hydrochloride (208 mg) as a white solid.
ESI MS m/e 406, M (free) + H+; 'HNMR (300 MHz, CDC13) 8 1.65-2.00 (m, 8 H), 2.26 (s, 3 H), 3.31
(s, 6 H), 3.98-4.27 (m, 2 H), 6.53-6.72 (m, 1 H), 7.20-7.27 (m, 1 H), 7.41-7.59 (m, 2 H), 7.64-7.73 (m,
1 H), 8.53-8.73 (m, 1 H), 12.76-12.95 (m, 1 H).
Example 3388
3-Chloro-7V-[ci5-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyI]-5-fluoro-
benzamide hydrochloride
Step A: Synthesis of 3-chIoro-7V-[cw-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylaniino)-
cyelohexyl]-5-fluoro-benzamide hydrochloride.
Using the procedure for the step A of example 3387, the title compound was obtained.
ESI MS m/e 406, M (free) + H+; 'HNMR (300 MHz, CDC13) 5 1.64-2.01 (m, 8 H), 2.26 (s, 3 H), 3.30
(s, 6 H), 4.02-4.25 (m, 2 H), 7.02-7.28 (m, 3 H), 7.46-7.53 (m, 1 H), 7.63-7.68 (m, 1 H), 8.48-8.60 (m,
1 H), 12.70-12.84 (m, 1 H).
Example 3389
Ar-[cw-4-(4-Dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-3,4,5-trifluoro-
benzamide hydrochloride
Step A: Synthesis of Ar-[cw-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-

789
3,4,5-trifluoro-benzamidehydrochloride.
Using the procedure for the step A of example 3387, the title compound was obtained.
ESI MS m/e 408, M (free) + H+; !H NMR (300 MHz, CDC13) 5 1.60-2.02 (m, 8 H), 2.26 (s, 3 H), 3.31
(s, 6 H), 4.01-4.26 (m, 2 H), 6.65-6.76 (m, 1 H), 7.21-7.29 (m, 1 H), 7.48-7.60 (m, 2 H), 8.57-8.69 (m,
1 H), 12.73-12.91 (m, 1 H).
Example 3390
iV-lC1-5^^-Dimethylamino-S-methyl-pyrimidin^-ylaminoVcyclohexylJ-S^-difluoro-
benzamide hydrochloride
Step A: Synthesis of A4c&-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-
cyclohexyl]-3,5-difluoro-benzamide hydrochloride.
Using the procedure for the step D of example 3119, the title compound was obtained.
ESI MS m/e 390, M (free) + if; !H NMR (300 MHz, CDC13) 6 1.61-2.06 (m, 8 H), 2.26 (s, 3 H), 3.31
(s, 6 H), 4.01-4.29 (m, 2 H), 6.55-6.70 (m, 1 H), 6.84-7.01 (m, 1 H), 7.18-7.43 (m, 3 H), 8.54-8.71 (m,
1H), 12.77-12.97 (m, 1 H).
Example 3391
2-(3,4-Difluoro-phenyI)-7V-[cw-4-(4-dimethylamino-5-methyl-pyrimidin-2-yIamino)-
cydohexyl]-acetamide hydrochloride
Step A: Synthesis of 2-(3,4-difluoro-phenyl)-7V-[cis-4-(4-dimethylamino-5-methyl-
pyrimidin-2-ylamino)-cyclohexyl]-acetamide hydrochloride.
Using the procedure for the step A of example 3387, the title compound was obtained.
ESI MS m/e 404, M (free) + H+; 'HNMR (300 MHz, CDC13) S 1.57-1.94 (m, 8 H), 2.24 (s, 3 H), 3.29
(s,6H), 3.47 (s, 2 H), 3.80-3.97 (m, 1 H), 4.05-4.18 (m, 1 H), 6.01-6.15 (m, 1 H), 6.95-7.28 (m, 4

790
H), 8.46-8.86 (m, 1 H), 12.81-13.01 (m, 1 H).
Example 3392
Ar-[cw-4-(4-Amino-5-methyl-pyrimidin-2-ylainino)-cyclohexyl]-3-chloro-4-fluoro-
benzamide hydrochloride
Step A: Synthesis of 2-chloro-5-methyl-pyrimidin-4-ylamine.
To the solution of 2,4-dichloro-5-methylpyrimidine (1.00 g) in IPA (2 mL) was added 28%
aqueous NH3 (2 mL). The mixture was heated in a microwave synthesizer at 120°C for 20 min. To the
mixture was added saturated aqueous NaHCO3 and the aqueous layer was extracted with CHC13 (three
times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by
medium-pressure liquid chromatography (NH-silica gel, 20% to 50% EtOAc in hexane) to give
2-chloro-5-methyl-pyrimidin-4-ylamine (151 mg) as a white solid.
ESI MS m/e 143, M+; *H NMR (300 MHz, DMSO-d6) 5 1.94 (s, 3 H), 7.81 (s, 1 H).
Step B: Synthesis of 7V-[c«-4-(4-amino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
3-chIoro-4-fluoro-benzamide hydrochloride.
Using the procedure for the step B of example 3228, the title compound was obtained.
ESI MS m/e 378, M (free) + H+; 'H NMR (300 MHz, DMSO-d6) 5 1.63-1.94 (m, 8 H), 1.91 (s, 3 H),
3.79-4.00 (m, 2 H), 7.52 (t, J= 8.9 Hz, 1 H), 7.63-7.70 (m, 1 H), 7.78-7.99 (m, 2 H), 8.07-8.13 (m,
1 H), 8.28-8.48 (m, 1 H), 11.86-11.96 (m, 1 H).
Example 3393
2-(3,4-Dichloro-phenoxy)-Ar-Icw-4-(4-dimethylamino-pyrimidin-2-ylamino)-
cyclohexylj-acetamide hydrochloride

791
Step A: Synthesis of 2-(3,4-dichloro-phenoxy)-Ar-[cw-4-(4-dimethylamino-pyrimidin-2-
ylamino)-cyclohexyl]-acetamide hydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e 438, M (free)+ ; !HNMR (300 MHz, CDC13) 5 1.59-2.03 (m, 8 H), 3.17 (s, 3 H), 3.27
(s, 3 H), 3.88-4.08 (m, 1 H), 4.11-4.25 (m, 1 H), 4.43 (s, 2 H), 5.96 (d, J= 7.5 Hz, 1 H), 6.66-6.79 (m,
1 H), 6.88 (dd, J= 8.9, 3.0 Hz, 1 H), 7.10 (d, J= 3.0 Hz, 1 H), 7.37 (d, J = 8.9 Hz, 1 H), 7.43-7.53 (m,
1 H), 8.69-8.83 (m, 1 H), 13.21 (brs, 1 H).
Example 3394
Ar-[ci5-4-(4-Dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-2-(3-methoxy-phenoxy)-
acetamide hydrochloride
Step A: Synthesis of 7V-[cry-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-2-(3-
methoxy-phenoxy)-acetamide hydrochloride.
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e 400, M (free) + H+ ; 'H NMR (300 MHz, CDC13) 5 1.63-2.03 (m, 8 H), 3.16 (s, 3 H),
3.27 (s, 3 H), 3.82 (s, 3 H), 3.92-4.08 (m, 1 H), 4.09-4.23 (m, 1 H), 4.45 (s, 2 H), 5.96 (d, J= 7.3 Hz,
1 H), 6.47-6.64 (m, 3 H), 6.75-6.90 (m, 1 H), 7.14-7.25 (m, 1 H), 7.40-7.56 (m, 1 H), 8.62-8.79 (m,
1 H), 13.29 (brs, I H).
Example 3395
iV-[c«-4-(4-Dimethylamino-pyrimidin-2-ylamino)-cyclohexyIJ-C-(ethyl-phenyl-amino)-
acetamide dihydrochloride
Step A: Synthesis of Ar-[c/5-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyI]-
C-(ethyl-phenyl-amino)-acetamide dihydrochloride.

792
Using the procedure for the step A of example 3198, the title compound was obtained.
ESI MS m/e 397, M (free) + H+ ; 'H NMR (300 MHz, DMSO-d6) 5 1.09 (t, J= 7.0 Hz, 3 H),
1.41-1.87 (m, 8 H), 3.14 (s, 3 H), 3.18 (s, 3 H), 3.43 (q,J= 7.0 Hz, 2 H), 3.60-3.80 (m, 1 H), 3.82-4.01
(m, 3H), 6.36 (d, J= 7.5 Hz, 1 H), 6.57-6.80 (m, 3 H), 7.06-7.28 (m, 2 H), 7.72-8.05 (m, 2 H),
8.20-8.42 (m, 1 H), 12.19 (brs, 1 H).
Example 3396
5-Chloro-JV-[cis-4-(4-methyl-quinoIin-2-yIamino)-cyclohexyl]-nicotinamide
Step A: Synthesis of 5-bromo-AL[ci.y-4-(4-methyl-quinolin-2-ylaniino)-cyclohexyl]-
nicotinamide.
To a solution of A/-(c/5-4-methyl-quinolin-2-yl)-cyclohexane-l,4-diamine obtained in step A of
example 3070 (5.00 g) in DMF (50 mL) were added 5-bromo-nicotinic acid (4.74 g), Et3N (6.55 mL),
HOBt-H2O (4.50 g), and EDC-HC1 (4.51 g). The reaction mixture was stirred at ambient temperature
for 16 hr. The reaction mixture was poured into saturated aqueous NaHCO3 and the aqueous layer
was extracted with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtered,
concentrated under reduced pressure, and purified by medium-pressure liquid chromatography
(NH-silica gel, 20% to 40% EtOAc in hexane) to give 5-bromo-/V-[c/5-4-(4-methyI-
quinolin-2-ylamino)-cyclohexyI]-nicotinamide (9.81 g) as a white solid.
ESI MS m/e 439, M + H"; 'HNMR (300 MHz, CDC13) 5 1.67-2.84 (m, 8 H), 2.58 (s, 3 H), 4.07-4.24
(m, 2 H), 4.72-4.83 (m, 1 H), 6.11-6.20 (m, 1 H), 6.52 (s, 1 H), 7.20-7.28 (m, 1 H), 7.49-7.81 (m, 3
H), 8.23-8.29 (m, 1 H), 8.79 (d,J = 2.3 Hz, 1 H), 8.86 (d, J= 1.9 Hz, 1 H).
Step B: Synthesis of 5-amino-iV-[c/s-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-
nicotinamide.
To the solution of 5-bromo-iV-[c^-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
nicotinamide (6.00 g) in EtOH (40 mL) were added copper (2.17 g), cuprous chloride (3.37 g), and

793
28% aqueous NH3 (40.0 mL). The mixture was stirred at 180°C for 4 hr in a sealed tube. The mixture
was filtrated through a pad of celite and the aqueous layer was extracted vvith CHCN (three times).
The combined organic layer was dried over MgSO4, filtered, concentrated under reduced pressure,
and purified by medium-pressure liquid chromatography (silica gel, 25% to 50% EtOAc in hexane) to
give 5-amino-Ar-[c/j-4-(4-methyI-quinolin-2-ylamino)-cyclohexyI]-nicotinamide (3.92 g) as a white
solid.
ESI MS m/e 376, M + H*; ]H NMR (300 MHz, CDC13) 5 1.66-2.04 (m, 8 H), 2.58 (s, 3 H), 3.88-4.24
(m, 4 H), 4.75-4.90 (m, 1 H), 6.18-6.31 (m, 1 H), 6.52 (s, 1 H), 7.19-7.29 (m, 1 H), 7.39-7.44 (m, 1
H), 7.48-7.58 (m, 1 H), 7.62-7.70 (m, 1 H), 7.73-7.80 (m, 1 H), 8.19 (d, J= 2.8 Hz, 1 H), 8.29 (d, J
= 1.6 Hz, 1 H).
Step C: Synthesis of 5-chIoro-Ar-[cis-4-(4-methyl-quinolin-2-yIamino)-cyclohexyl]-
nicotin amide.
A mixture of cone. HC1 (1.33 mL) and NaNO2 (137.8 mg) was stirred at 70 °C for 10 min and
cooled to ambient temperature. To the reaction mixture was added a solution of 5-amino-TV-[c 15-4-
(4-methyI-quinolin-2-ylamino)-cyclohexyI]-nicotinamide (500 mg) in AcOH (45 mL) and the mixture
was stirred at ambient temperature for 30 min. To the reaction mixture was added a solution of CuCl
(460.8 mg) in cone. HCI (3.0 mL) and the mixture was stirred at 80 °C for 6 hr. The reaction mixture
was alkalized with 1M aqueous NaOH and the aqueous layer was extracted with CHCI3 (three times).
The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by flash
chromatography (NH-silica gel, 20% EtOAc in hexane and silica gel, 2% MeOH in CHC13) to give
5-chloro-7V-[c/5-4-(4-methyl-quino!in-2-ylamino)-cyclohexyl]-nicotinamide (52.3 mg) as a yellow
solid.
ESI MS m/e 395, M (free) + H+ ; lH NMR (300 MHz, CDC13) 5 1.65-2.03 (m, 8 H); 2.57 (s, 3 H),
4.03-4.29 (m, 2 H), 5.05 (brs, 1 H), 6.33-6.44 (m, 1 H), 6.53 (s, 1 H), 7.19-7.28 (m, 1 H), 7.48-7.56
(m, 1 H), 7.61-7.67 (m, 1 H), 7.73-7.79 (m, 1 H), 8.08-8.13 (m, 1 H), 8.66 (d, J= 2.3 Hz, 1 H), 8.83
(d, .7=1.9 Hz, 1 H).

794
Example 3397
5-Fluoro-Ar-[c/5-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-nicotinamide
Step A: Synthesis of 5-fluoro-7V-[c«-4-(4-methyl-quinolin-2-ylamino)-cyclohexylJ-
nicotin amide.
To a solution of 5-amino-Ar-[cf5-4-(4-methyI-quinolin-2-ylamino)-cyclohexyI]-
nicotinamide obtained in step B of example 3396 (500 mg) in 48% aqueous HBF4 (3.95 mL) and
EtOH (4.00 mL) was added CuF2 (132.0 mg) at ambient temperature. To the reaction mixture was
added a solution of NaNO? (183.5 mg) in H2O (3.95 mL) and the mixture was stirred at ambient
temperature for 1 hr. Then the mixture was stirred at 50°C for 2 hr and 80°C for 2 hr. The reaction
mixture was alkalized with 1M aqueous NaOH and the aqueous layer was extracted with EtOAc (three
times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by
flash chromatography (NH-silica gel, 50% EtOAc in hexane) to give
5-fluoro-7(/-[c/j-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-nicotinamide (20.9 mg) as a yellow
amorphous.
ESI MS m/e 379, M (free) + H+ ; ]H NMR (300 MHz, CDCI3) 6 1.67-2.05 (m, 8 H), 2.57 (s, 3 H),
4.08-4.25 (m, 2 H), 4.72 (brs, 1 H), 6.17-6.29 (m, 1 H), 6.52 (s, 1 H), 7.19-7.28 (m, 1 H), 7.48-7.57
(m, 1 H), 7.62-7.69 (m, 1 H), 7.73-7.80 (m, 1 H), 7.82-7.91 (m, 1 H), 8.60 (d, J= 2.8 Hz, 1 H), 8.76
(t,J=1.5Hz, 1 H).
Example 3398
3-chloro-Ar-[c/5-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyC1-5hexyl]-4-fluoro-
benzamide methanesulfonic acid
Step A: Synthesis of 3-chloro-Ar-[c/s-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-
cyc!ohexyl]-4-fluoro-benzamide methanesulfonic acid.

795
To a solution of A^-(cz5-4-amino-cyclohexyI)-3-chloro-4-fluoro-benzamide obtained in step A
of example 3228 (1.76 g) in BuOH (2.5 mL) was added 2-chloro-4-dimethylamino-5-
methylpyrimidine obtained in step A of example 3119 (1.00 g). The mixture was heated in a
microwave synthesizer at 200°C for 15 min. The reaction was repeated 3 more times and the reaction
mixtures were pooled. The mixture was poured into saturated aqueous NaHCO3 and the aqueous
layer was extracted with CHC13 (three times). The combined organic layer was dried over MgSO4,
filtrated, concentrated under reduced pressure, and purified by medium-pressure liquid
chromatography (NH-silica gel, 15% to 80% EtOAc in nexane) to give a colorless solid. To a solution
of the above solid (1.85 g) in EtOH (18 mL) was added MsOH (460 mg). The mixture was stirred at
ambient temperature for 30 min and stirred on an ice-bath for 4 hr. The precipitate was collected by
filtration, washed with EtOH, and dried at 80°C under reduced pressure to give 3-chloro-Ar-[c/5-4-(4-
dimethylamino-5-methyI-pyrimidin-2-ylamino)-cyC1-5hexyl]-4-fluoro-benzamidemethanesulfonic
acid (1.41 g) as a white solid.
ESI MS m/e 406, M (free) + H+; 'H NMR (300 MHz, CDC13) 5 1.60-2.03 (m, 8 H), 2.25 (s, 3 H), 2.89
(s, 3 H), 3.30 (s, 6 H), 4.07-4.30 (m, 2 H), 7.13-7.29 (m, 2 H), 7.38-7.49 (m, 1 H), 7.81-7.89 (m, 1
H), 7.96-8.05 (m, 1 H), 8.07 (dd, J= 7.1, 2.3 Hz, 1 H), 12.07-12.23 (m, 1 H).

796
Assay Procedures
Example 3399
ASSAY FOR DETERMINATION OF CONSTITUTIVE ACTIVITY OF GPCRS
A. Intracellular IP3 Accumulation Assay
On day 1, cells to be tranfected can be plated onto 24 well plates, usually lxlO5 cells/well
(although his umber can be optimized. On day 2 cells can be transfected by firstly mixing 0.25ug
DNA (e.g., pC1-5V vector or pC1-5V vector comprising polynucleotide enocoding receptor) in 50 ul
serum free DMEM/well and 2 ul lipofectamine in 50 ul serum-free DMEM/well. The solutions are
gently mixed and incubated for 15-30 min at room temperature. Cells are washed with 0.5 ml PBS
and 400 (4.1 of serum free media is mixed with the transfection media and added to the cells. The cells
are then incubated for 3-4 hrs at 37°C/5%CO2 and then the transfection media is removed and
replaced with lml/well of regular growth media. On day 3 the cells are labeled with 3H-myo-inositoI.
Briefly, the media is removed and the cells are washed with 0.5 ml PBS. Then 0.5 ml
inositol-free/serum free media (GIBCO BRJL) is added/well with 0.25 uCi of 3H-myo-inositol/ well
and the cells are incubated for 16-18 hrs o/n at 37°C/5%CO2 On Day 4 the cells are washed with 0.5
ml PBS and 0.45 ml of assay medium is added containing inositol-free/serum free media lOuM
pargyline 10 mM lithium chloride or 0.4 ml of assay medium and 50 ul of lOx ketanserin (ket) to
final concentration of lOuM. The cells are then incubated for 30 min at 37°C. The cells are then
washed with 0.5 ml PBS and 200 ul of fresh/ice cold stop solution (1M KOH; 18 mM Na-borate; 3.8
mMEDTA) is added/well. The solution is kept on ice for 5-10 min or until cells were lysed and then
neutralized by 200 fil of fresh/ice cold neutralization sol. (7.5 % HCL). The lysate is then transferred
into 1.5 ml eppendorf tubes and 1 ml of chloroform/methanol (1:2) is added/tube. The solution is
vortexed for 15 sec and the upper phase is applied to a Biorad AG1-X8™ anion exchange resin
(100-200 mesh). Firstly, the resin is washed with water at 1:1.25 W/V and 0.9 ml of upper phase is
loaded onto the column. The column is washed with 10 mis of 5 mM myo-inositol and 10 ml of 5
mM Na-borate/60mM Na-formate. The inositol tris phosphates are eluted into scintillation vials
containing 10 ml of scintillation cocktail with 2 ml of 0.1 M formic acid/ 1 M ammonium formate.
The columns are regenerated by washing with 10 ml of 0.1 M formic acid/3M ammonium formate

797
and rinsed twice with H20 and stored at 4°C in water.
Example 3400
High Throughput Functional Screening: FLIPR™
Subsequently, a functional based assay was used to confirm the lead hits, referred to as
FLIPR™ (the Fluorometric Imaging Plate Reader) and FDSS6000™ (Functional Drug Screening
System). This assay utilized a non-endogenous, constitutively active version of the MCH receptor.
The FLIPR and FDSS assays are able to detect intracellular Ca2+ concentration in cells,
which can be utilized to assess receptor activation and determine whether a candidate compound is
an, for example, antagonist, inverse agonist or agonist to a Gq-coupled receptor. The concentration
of free Ca2+ in the cytosol of any cell is extremely low, whereas its concentration in the extracellular
fluid and endoplasmic reticulum (ER) is very high. Thus, there is a large gradient tending to drive
Ca2+ into the cytosol across both the plasma membrane and ER. The FLIPR™ and FDSS6000™
systems (Molecular Devices Corporation, HAMAMATSU Photonics K.K.) are designed to perform
functional cell-based assays, such as the measurement of intracellular calcium for high-throughput
screening. The measurement of fluorescent is associated with calcium release upon activation of the
Gq-coupled receptors. Gi or Go coupled receptors are not as easily monitored through the FLIPR™
and FDSS6000™ systems because these G proteins do not couple with calcium signal pathways.
Fluorometric Imaging Plate Reader system was used to allow for rapid, kinetic
measurements of intracellular fluorescence in 96 well microplates (or 384 well microplates).
Simultaneous measurements of fluorescence in all wells can be made by FLIPR or FDSS6000 M
every second with high sensitivity and precision. These systems are ideal for measuring cell-based
functional assays such as monitoring the intracellular calcium fluxes that occur within seconds after
activation of the Gq coupled receptor.
Briefly, the cells are seeded into 96 well at 5.5x10 cells/well with complete culture media
(Dulbecco's Modified Eagle Medium with 10 % fetal bovine serum, 2 mM L-glutamine, 1 mM
sodium pyruvate and 0.5 mg/ml G418, pH 7.4) for the assay next day. On the day of assay, the media
is removed and the cells are incubated with 100 p.1 of loading buffer (4 uM Fluo4-AM in complete

798
culture media containing 2.5 mMProbenicid, 0.5 mg/ml and 0.2% bovine serum albumin) in5%CO2
incubator at 37°C for 1 hr. The loading buffer is removed, and the cells are washed with wash buffer
(Hank's Balanced Salt Solution containing 2.5 mM Probenicid, 20 mM HEPES, 0.5 mg/ml and 0.2%
bovine serum albumin, pH 7.4)). One hundred fifty fil of wash buffer containing various
concentrations of test compound is added to the cells, and the cells are incubated in 5% CO?
incubator at 37°C for 30 min. Fifty u.1 of wash buffer containing various concentration of MCH are
added to each well, and transient changes in [Ca +]i evoked by MCH are monitored using the FLIPR
or FDSS in 96 wel) plates at Ex. 488 nm and Em. 530 nm for 290 second. When antagonist activity
of compound is tested, 50 nM of MCH is used.
Use of FLIPR™ and FDSS6000™ can be accomplished by following manufacturer's
instruction (Molecular Device Corporation and HAMAMATSU Photonics K.K.).
Representative examples are shown below.

Compound No. IC50 (nM)
Example 7 11
Example 15 19
Example 19 21
Example 2524 2.1
Example 2526 7.6
The results were shown on the tables in the Examples section and the table in the next page in
accordance with the classification as defined below.
Class 1 : The value of percent of control at 10"7 M was less than 40% or the value of IC50
was less than 50 nM.
Class 2 : The value of percent of control at 10"7 M was from 40% to 60% or the value of IC50

799
was from 50 nM to 200 nM.
Class 3 : The value of percent of control at 10'7 M was more than 60% or the value of IC50
was more than 200 nM.
The compounds in Examples 2497 to 2542, 2588 to 2689, and 3241 to 3259 were tested and
they showed IC50 activities less than about 50 \JM.

Ex. No. class Ex. No. class Ex. No. class Ex. No. class Ex. No. class Ex. No. class
1 2 3058 1 3104 2 3150 3196 2 3384 1
2 2 3059 1 3105 2 3151 1 3197 2 3385 1
1 3060 2 3106 1 3152 1 3198 1 3386 1
4 1 3061 1 3107 1 3153 1 3199 1 3387 1
5 2 3062 1 3108 1 3154 1 3200 3 3388 1
6 2 3063 1 3109 1 3155 ■t 3201 1 3389 1
7 1 3064 1 3110 1 3156 -> 3202 1 3390 1
8 1 3065 I 3111 1 3157 2 3203 1 3391 1
9 3 3066 1 3112 1 3158 1 3204 2 3392 3
10 2 3067 2 3113 3159 1 3205 2 3393 1
11 1 3068 2 3114 1 3160 1 3206 1 3394 1
12 2 3069 2 3115 1 3161 2 3207 1 3395 1
13 3 3070 1 3116 3 3162 2 3208 3 3396 1
14 1 3071 1 3117 1 3163 1 3209 3 3397 1
15 1 3072 ■ 1 3118 3 3164 2 3210 -i 3398 1
16 1 3073 1 3119 1 3165 2 3211 1
17 2 3074 1 3120 1 3166 1 3212 3

18 1 3075 1 3121 1 3167 1 3213 3

19 1 3076 1 3122 1 3168 1 3214 2


800

3031 1 3077 1 3123 1 3169 1 3215 2
3032 1 3078 1 3124 1 3170 1 3216 1
3033 1 3079 1 3125 1 3171 2 3217 1
3034 1 3080 1 3126 1 3172 1 3218 -»
3035 1 3081 1 3127 1 3173 3219 2
3036 1 3082 1 3128 1 3174 1 3220 1
3037 -> 3083 1 3129 2 3175 1 3221 1
3038 1 3084 1 3130 3 3176 2 3222 1
3039 1 3085 1 3131 -i 3177 2 3223
3040 1 3086 1 3132 3 3178 2 3224 2
3041 1 3087 1 3133 -> 3179 1 3225 3
3042 1 3088 1 3134 3180 1 3226 3
3043 1 3089 1 3135 3181 2 3227 3
3044 2 3090 1 3136 J 3182 -> 3228 1
3045 1 3091 1 3137 2 3183 i 3229 1
3046 1 3092 1 3138 2 3184 2 3230 1
3047 I 3093 1 3139 2 3185 1 3231 2
3048 1 3094 1 3140 2 3186 2 3232 2
3049 1 3095 1 3141 2 3187 3 3233 ->
3050 1 3096 1 3142 3188 1 3234
3051 1 3097 1 3143 3189 1 3235 1
3052 1 3098 1 3144 3190 2 3236
3053 1 3099 1 3145 3 3191 2 3237 *>
3054 1 3100 1 3146 1 3192 1 3238 1
3055 1 3101 1 3147 2 3193 1 3239 1
3056 1 3102 1 3148 3194 1 3240 1
3057 1 3103 2 3149 2 3195 2 3383 1

801
Example 3401
Receptor Binding Assay
In addition to the methods described herein, another means for evaluating a test compound is
by determining binding affinities to the MCH receptor. This type of assay generally requires a
radiolabelled ligand to the MCH receptor. Absent the use of known ligands for the MCH receptor
and radiolabels thereof, compounds of Formula (I) can be labelled with a radioisotope and used in an
assay for evaluating the affinity of a test compound to the MCH receptor.
A radiolabelled MCH compound of Formula (I) can be used in a screening assay to
identify/evaluate compounds. In general terms, a newly synthesized or identified compound (i.e.,
test compound) can be evaluated for its ability to reduce binding of the "radiolabelled compound of
Formula (I)" to the MCH receptor. Accordingly, the ability to compete with the "radio-labelled
compound of Formula (I)" or Radiolabelled MCH Ligand for the binding to the MCH receptor
directly correlates to its binding affinity of the test compound to the MCH receptor.
ASSAY PROTOCOL FOR DETERMINING RECEPTOR BINDING FOR MCH:
A. MCH RECEPTOR PREPARATION
293 cells (human kidney, ATCC), transiently transfected with 10 ug human MCH receptor
and 60 ul Lipofectamine (per 15-C1-5 dish), are grown in the dish for 24 hours (75% confluency) with
a media change and removed with 10 ml/dish of Hepes-EDTA buffer (20mM Hepes + 10 mM EDTA,
pH 7.4). The cells are then centrifuged in a Beckman Coulter centrifuge for 20 minutes, 17,000 rpm
(JA-25.50 rotor). Subsequently, the pellet is resuspended in 20 mM Hepes + 1 mM EDTA, pH 7.4
and homogenized with a 50- ml Dounce homogenizer and again centrifuged. After removing the
supernatant, the pellets can be stored at -80°C, until used in binding assay. When used in the assay,
membranes are thawed on ice for 20 minutes and then 10 mL of incubation buffer (20 mM Hepes, 1
mM MgCl2, 100 mM NaCl, pH 7.4) added. The membranes are then vortexed to resuspend the crude
membrane pellet and homogenized with a Brinkmann PT-3100 Polytron homogenizer for 15 seconds
at setting 6. The concentration of membrane protein is determined using the BRL Bradford protein
assay.

802
B. BINDING ASSAY
For total binding, a total volume of 50ul of appropriately diluted membranes (diluted in
assay buffer containing 50mM Tris HC1 (pH 7.4), 1 OmM MgCl2, and lmM EDTA; 5-50ug protein) is
added to 96-well polyproylene microtiter plates followed by addition of 1 OOul of assay buffer and
50ul of Radiolabelled MCH Ligand. For nonspecific binding, 50 ul of assay buffer is added instead
of lOOul and an additional 50ul of lOuM cold MCH is added before 50ul of Radiolabelled MCH
Ligand is added. Plates are then incubated at room temperature for 60-120 minutes. The binding
reaction is terminated by filtering assay plates through a Microplate Devices GF/C Unifilter filtration
plate with a Brandell 96-well plate harvestor followed by washing with cold 50 mM Tris HC1, pH 7.4
containing 0.9% NaCI. Then, the bottom of the filtration plate are sealed, 50 u,l of Optiphase
Supermix is added to each well, the top of the plates are sealed, and plates are counted in a Trilux
MicroBeta scintillation counter. For compound competition studies, instead of adding 100 }i\ of
assay buffer, 100 [i\ of appropriately diluted test compound is added to appropriate wells followed by
addition of 50 ul of Radiolabelled MCH Ligand.
C. CALCULATIONS
The test compounds are initially assayed at 1 and 0.1 fiM and then at a range of
concentrations chosen such that the middle dose would cause about 50% inhibition of a
Radiolabelled MCH Ligand binding (i.e., IC50). Specific binding in the absence of test compound
(Bo) is the difference of total binding (BT) minus non-specific binding (NSB) and similarly specific
binding (in the presence of test compound) (B) is the difference of displacement binding (BD) minus
non-specific binding (NSB). IC50 is determined from an inhibition response curve, logit-log plot
of % B/Bo vs concentration of test compound.
Kj is calculated by the Cheng and Prustoff transformation:
K, = IC50/(l + [L]/KD)
wherein [L] is the concentration of a Radiolabelled MCH Ligand used in the assay and KD
is the dissociation constant of a Radiolabelled MCH Ligand determined independently under the

803
same binding conditions.
It is intended that each of the patents, applications, printed publications, and other published
documents mentioned or referred to in this specification be herein incorporated by reference in their
entirety.
Those skilled in the art will appreciate that numerous changes and modifications may be
made to the preferred embodiments of the invention and that such changes and modifications may be
made without departing from the spirit of the invention. It is therefore intended that the appended
claims cover all such equivalent variations as fall within the true spirit and scope of the invention.

804
CLAIMS
A compound of Formula (I):

wherein Q is:

Ri is selected from the group consisting of:
(i) C1-16 alkyl, and
C1-16 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
"OXO,
•C1-5 alkoxy,
•Ci_; alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••carbocyclic aryl,
••heterocyclyl, and
••heterocyclyl substituted by C1-5 alkyl,
•Cj.5 alkylcarbonyloxy,

805
•carbocyclyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••hydroxy,
••carboxy,
••carbamoyl,
••nitro,
••cyano,
••amino,
••carbocyclic aryl,
••carbocyclic aryl substituted by C1-5 alkoxy,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
—halogen,
•••hydroxy,
•••carboxy,
•••oxo,
•••mono-C1-5 alkylamino,
•••di-C1-5 alkylamino,
•••mono-C^ alkylamino substituted by carbocyclic aryl,
•••di-C1-5 alkylamino substituted by carbocyclic aryl,
•••mono-C1-5 alkylamino substituted by halogenated
carbocyclic aryl,

806
••■di-C1-5 alkylamino substituted by halogenated
carbocyclic aryl,
—carbocyclic arylcarbonylamino, and
•••carbocyclic arylcarbonylamino substituted by halogen,
"heterocyclyloxy,
•heterocyclyloxy substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••carboxy,
••carbamoyl,
••nitro,
••cyano,
••amino,
••carbocyclic aryl,
••carbocyclic aryl substituted by C1-5 alkoxy,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by substituent(s) independently selected
from the group consisting of:
—halogen,
—hydroxy, and
•••carboxy,
••C1-5 alkyl, and
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••hydroxy, and
•••carboxy,

807
•substituted heterocyclyl-ethylideneaminooxy,
•C1-5 alkoxycarbonyl,
•Ci-s alkoxycarbonyl substituted by carbocyclic aryl,
•mono-C1-5 alky lam inocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by substituent(s) independently selected
from the group consisting of:
••cyano,
••carbocyclic aryl, and
••heterocyclyl,
•di-C1-5 alkylamino,
•di-C1-5 alkylamino substituted by substituent(s) independently selected
from the group consisting of:
••cyano,
••carbocyclic aryl, and
••heterocyclyl,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
—hydroxy,
••carboxy,
••carbamoyl,
••nitro,
••cyano,
••amino,
••carbocyclic aryl,

808
••carbocyclic aryl substituted by C1-5 alkoxy,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••hydroxy, and
••• carboxy,
••C1-5 alkyl, and
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••hydroxy, and
•••carboxy,
•di-carbocyclic arylamino,
•di-carbocyclic arylamino substituted by substituent(s) independently
selected from the group consisting of:
"•halogen,
"hydroxy,
"carboxy,
••carbamoyl,
••nitro,
••cyano,
••amino,
"carbocyclic aryl,
"carbocyclic aryl substituted by Cj.5 alkoxy,
"C1-5 alkoxy,
••C1-5 alkoxy substituted by substituent(s) independently selected
from the group consisting of:

809
•••halogen,
•••hydroxy, and
•••carboxy,
••C1-5 alkyl, and
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
—halogen,
•••hydroxy, and
•••carboxy,
•mono-heterocyclylamino,
•mono-heterocyclylamino substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
••hydroxy,
••carboxy,
••carbamoyl,
••nitro,
••cyano,
••amino,
••carbocyclic aryl,
••carbocyclic aryl substituted by C^5 alkoxy,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••hydroxy, and
•••carboxy,
••C1-5 alkyl, and

810
"C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••hydroxy, and
—carboxy,
•di-heterocyclylamino,
•di-heterocyclylamino substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••hydroxy,
••carboxy,
••carbamoyl,
••nitro,
••cyano,
••amino,
••carbocyclic aryl,
••carbocyclic aryl substituted by C1-5 alkoxy,
"C1-5 alkoxy,
••C1-5 alkoxy substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••hydroxy, and
•••carboxy,
••Ci-g alkyl, and
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••hydroxy, and

811
•••carboxy,
•C1-5 alkylcarbonylamino,
•C1-5 alkylcarbonylamino substituted by substituent(s) independently
selected from the group consisting of:
••C1-5 alkylcarbonylamino,
••carbocyclic arylcarbonylamino, and
••heterocyclyl,
•C|.5 alkoxycarbonylamino,
•carbocyclic arylcarbonylamino,
•heterocyclyl carbonylamino,
•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted by substituent(s) independently
selected from the group consisting of:
••nitro,
••C1-5arkyI,
••mono-C1-5 alkylamino, and
••di-C1-5 alkylamino,
•C^alkylthio,
•C1-5 alkylthio substituted by substituent(s) independently selected from
the group consisting of:
••mono-carbocyclic arylaminocarbonyl,
••mono-carbocyclic arylaminocarbonyl substituted by halogen,
••di-carbocyclic arylaminocarbonyl,
••di-carbocyclic arylaminocarbonyl substituted by halogen,
••mono-carbocyclic arylamino,
••mono-carbocyclic arylamino substituted by halogen,
••di-carbocyclic arylamino,
•*di-carbocyclic arylamino substituted by halogen,

812
••carbocyclic aryl, and
"carbocyclic aryl substituted by substituent(s) independently
selected from the group consisting of:
•••halogen, and
•••C1-5 alkoxy,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
"C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
•carbocyclic arylsulfinyl,
•carbocyclic arylsulfinyl substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
"C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
"C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
•heterocyclylthio,
•heterocyclylthio substituted by substituent(s) independently selected from
the group consisting of:
••nitro, and
"C1-5 alkyl,

813
•C3-6 cycloalkyl,
•C3-6 cycloalkyl substituted by C1-5 alkyl,
•C3-6 cycloalkyl substituted by carbocyclic aryl,
•C3-6 cycloalkenyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C1-5 alkyl,
••C1-5 alkoxy,
••C2_5 alkenyl, and
••C2.5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•'•carbocyclic aryl, and
"••carbocyclic aryl substituted by C1-5 alkylsulflnyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••carboxy,
••carbamoyl,
••cyano,
••nitro,
••amino,
••C1-5 alkylcarbonylamino,
••C3-6 cycloalkylcarbonylamino,
»C1-5 alkyl,

814
"C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••hydroxy,
•••carboxy,
•••carbamoyl,
•••oxo,
•••carbocyclic aryl,
•••heterocyclyl,
—mono-carbocyclic arylamino.,
—di-carbocyclic arylamino,
•••mono-carbocyclic arylamino substituted by
substituent(s) independently selected from the group
consisting of:
••••halogen,
••••nitro,
••••C1-5 alkyl,
••••C1-5 alkoxy, and
••••C1-5 alkoxy substituted by halogen,
•••di-carbocyclic arylamino substituted by substituent(s)
independently selected from the group consisting of:
••••halogen,
••••nitro,
••••Ct.5 alkyl,
"••C1-5 alkoxy, and
••••C1-5 alkoxy substituted by halogen,
••C2-5 alkenyl,
••C1-5 alkoxy,

815
"Q.5 alkoxy substituted by substituent(s) independently selected
from the group consisting of:
•••halogen, and
•••carbocyclic aryl,
••carbocyclic aryloxy,
••C1-5 alkoxycarbonyl,
••C1-5 alkylcarbonyloxy,
••mono-Cj.5 alkylamino,
••di-C1-5 alkylamino,
••mono-carbocyclic arylamino,
••mono-carbocyclic arylamino substituted by halogen,
••di-carbocyclic arylamino,
••di-carbocyclic arylamino substituted by halogen,
••mono-carbocyclic arylaminocarbonyl,
••mono-carbocyclic arylaminocarbonyl substituted by
substituent(s) selected from the group consisting of:
•••halogen,
—nitro,
•••C1-5 alkyl,
•••C1-5 alkoxy, and
•••C1-5 alkoxy substituted by halogen,
••di-carbocyclic arylaminocarbonyl,
••di-carbocyclic arylaminocarbonyl substituted by substituent(s)
selected from the group consisting of:
•••halogen,
• "nitro,
•"•C1-5 alkyl,
•••C1-5 alkoxy, and

816
•••C1-5 alkoxy substituted by halogen,
••mercapto,
••C[.5alkylthio,
••C1-5 alkylthio substituted by halogen,
••C1-5 alkylsulfonyl,
••C3-6 cycloalkyl,
••carbocyclic aryl, and
••heterocyclyl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••hydroxy,
••carboxy,
••carbamoyl,
••cyano,
••nitro,
•*amino,
-C1-5 alkyl,
••Ct_5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
—halogen,
—hydroxy,
"••carboxy, and
"••carbamoyl,
•*C1-5 alkyl substituted by carbocyclic aryl,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by halogen,

817
••C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryl, and
••carbocyclic aryl substituted by halogen,
(ii) C2-8 alkenyl, and
C2-8 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••nitro,
"C1-5 alkyl,
"C1-5 alkyl substituted by halogen,
••C1-5 alkoxy, and
••C1-5 alkoxy substituted by halogen,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••hydroxy,
••nitro,
••Cj-5 alkyl, and
••C1-5 alkoxy,
(iii) C2-5 alkynyl, and

818
C2-5 alkynyl substituted by carbocyclic aryl,
(iv) C3.12 cycloalkyl, and
C3-12 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:
•d_5 alky],
■C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••hydroxy,
••oxo, and
••carbocyclic aryl,
•mono-C1-5 alkylamino.,
•mono-C1-5 alkylamino substituted by carbocyclic aryl,
•di-C1-5 alkylamino,
•di-C1-5 alkylamino substituted by carbocyclic aryl,
•carbocyclic arylcarbonylamino,
•carbocyclic aryl, and
•carbocyclic aryi substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
"C1-5 alkoxy,
••C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
(v) C3-6 cycloalkenyl, and
C3-6 cycloalkenyl substituted by C1-5 alkyl,
(vi) carbocyclyl, and
carbocyclyl substituted by substitutent(s) independently selected from the
group consisting of:
•hydroxy, and

819
•nitro,
(vii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
"hydroxy,
•cyano,
•nitro,
•Cj.io alkyl,
•C1-5O alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••hydroxy,
••carboxy,
••carbamoyl,
"OXO,
••C1-5 alkoxy,
••carbocyclic aryloxy,
••mono-C1-5 alky lam ino-N-oxy,
••di-C1-5 alky lam ino-N-oxy,
••mono-C1-5 alkylamino,
••di-C1-5 alkylamino,
••mono-C1-5 alkylamino substituted by carbocyclic aryl,
••di-Ct.5 alkylamino substituted by carbocyclic aryl,
••mono-carbocyclic arylamino,
••di-carbocyclic arylamino,
••carbocyclylimino,
••carbocyclylimino substituted by carbocyclic aryl,

820
••mono-carbocyclic arylamino,
••di-carbocyclic arylamino,
••mono-carbocyclic arylamino substituted by C1-5 alkoxy,
••di-carbocyctic arylamino substituted by C1-5 alkoxy,
'•mono-carbocyclic arylaminocarbonyl,
••di-carbocyclic arylaminocarbonyl,
••mono-carbocyclic arylaminocarbonyl substituted by C1-5 alkoxy,
•*di-carbocyclic arylaminocarbonyl substituted by C\.5 alkoxy,
••carbocyclic aryl,
••carbocyclic aryl substituted by substituent(s) independently
selected from the group consisting of:
•••halogen,
•••C1-5 alkyl, and
•••C1-5 alkyl substituted by halogen,
••heterocyclyl, and
••heterocyclyl substituted by C^5 alkyl,
•C2.5 alkenyl,
•C2-5 alkenyl substituted by carbocyclic aryl,
•C1-9 alkoxy,
•C1.9 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••hydroxy,
—halogen,
••carboxy,
••mono-C1-5 alkylamino,
•*di-C|_5 alkylamino,
••carbocyclic aryl,
••halogenated carbocyclic aryl,

821
••heterocyclyl,
••heterocyclyl substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
—heterocyclyl, and
•••heterocyclyl substituted by substituent(s) independently
selected from the group consisting of:
••••halogen,
••••C1-5 alkyl, and
••••C1-5 alkyl substituted by halogen,
•C2.5 alkenyloxy,
•C3^ cycloalkoxy,
•Ct_5 alkylcarbonyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••hydroxy,
••carboxy,
••carbamoyl,
••cyano,
••nitro,
••amino,
••C1-5 alkyl,
"C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••hydroxy,

822
•••carboxy, and
•••carbamoyl,
"C1-5 alkoxy, and
••C1-5 alkoxy substituted by halogen,
•heterocyclyloxy,
•heterocyclyloxy substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••carboxy,
••carbamoyl,
••cyano,
••nitro,
••amino,
"C1-5 alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••hydroxy,
•••carboxy, and
•••carbamoyl,
••C1-5 alkoxy, and
"C1-5 alkoxy substituted by halogen,
•(carbocyclic aryl)S(O)2O,
•carboxy,
•carbamoyl,
•C1-5 alkoxycarbonyl,
•mono-C1-5 alkylaminocarbonyl,

823
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•mono-carbocyclic arylaminocarbonyl,
•di-carbocyclic arylaminocarbonyl,
•mono-carbocyclic arylaminocarbonyl substituted by C1-5 alky],
•di-carbocyclic arylaminocarbonyl substituted by C1-5 alkyl,
•amino,
•mono-Cj.5 alkylamino,
•di-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino substituted by cyano,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•C1-5 alkylcarbonylamino,
•C3-6 cycloalkylcarbonylamino,
•C2-5 alkynylcarbonylamino,
•C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,
•C1-5 alkoxycarbonylamino,
•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted by C1-5 alkyl,
•(carbocyclic aryl)NHC(O)NH,
•(carbocyclic aryl)NHC(O)NH substituted by C1-5 alkoxy,
•(carbocyclic aryl)NHC(O)NH substituted by haloganated C1-5 alkoxy,
•carbocyclic aryl azo,
•carbocyclic aryl azo substituted by mono-C1-5 alkylamino,
•carbocyclic aryl azo substituted by di-C1-5 alkylamino,
•Ct-5 alkylthio,

824
•C1-5 alkylthio substituted by halogen,
'carbocyclic arylthio,
•carbocyclic arylthio substituted by substituent(s) independently selected
from the group consisting of:
—halogen,
••nitro,
••cyano, and
••C.5 alkyl,
•aminosulfonyl,
• heterocycly lth io,
•C1-5 alkylsulfonyl,
•mono-C1-5 alkylaminosulfonyl,
•di-Cj.5 alkylaminosulfonyl,
•heterocyclylsulfonyl,
•C3-6 cycloalkyl,
•C3-6 cycloalkyl substituted by d_5 alkyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••C1.7 alkyl, and
••C1.7 alkyl substituted by halogen,
•heterocycly 1, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
"C1-5 alkyl,
••carbocyclic aryl, and
••halogenated carbocyclic aryl,
"C[.5 alkoxycarbonyl substituted by carbocyclic aryl, and

825
(viii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•carboxy,
•carbamoyl,
•cyano,
•nitro,
•amino,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••hydroxy,
••carboxy,
••carbamoyl,
••oxo,
••C1-5 alkylcarbonyloxy,
••carbocyclic arylcarbonylamino,
••carbocyclic arylcarbonylamino substituted by halogen,
••C1-5 alkoxycarbonyl,
••C1-5 alkylthio,
••C1-5 alkylthio substituted by carbocyclic aryl,
••Ci.s alkylthio substituted by halogenated carbocyclic aryl,
•"carbocyclic aryl,
••carbocyclic aryl substituted by substituent(s) independently
selected from the group consisting of:

826
•••halogen, and
•••nitro,
••heterocyclyl, and
••heterocyclyl substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••C1-5 alkyl, and
—C1-5 alkyl substituted by halogen,
•Ci_s alkoxy,
•C1-5 alkoxy substituted by halogen,
•Cj-s alkoxy substituted by carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••nitro,
••cyano,
••hydroxy,
••carboxy,
••carbamoyl,
••amino,
••C1-5 alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••hydroxy,
•••carboxy, and
•••carbamoyl,

827
"mono-C1-5 alkylamino,
••di-C]o alkylamino,
"•C1-5 alkylcarbonylamino,
••C3-6 cycloalkycarbonylamino,
•"C1-5 alkoxy,
•■Ci_s alkoxy substituted by halogen,
••C3-6 cycloalkyl,
••C2_5 alkenyl,
••C2-5alkynyl,
••carboxy,
**C1-5 alkoxycarbonyl,
••mono-C1-5 alkylaminocarbonyl,
••di-C1-5 alkylaminocarbonyl,
••mono-C3-6 cycloalkylaminocarbonyl,
••di-C3-6cycloalkyIaminocarbonyl,
••mono-C1-5 alky lam inocarbony lam ino,
"di-Ci-g alkylaminocarbonylamino,
"mono-C3-6CycloalkylaminocarbonyIamino,
••di-C3-6cycloalkylaminocarbonylamino,
"C1-5 alkylthio,
"C1-5 alkylthio substituted by halogen,
*#C1-5 alkylsulfinyl,
••C]-5 alkylsulfinyl substituted by halogen,
"C1-5 alkylsulfonyl, and
••C1-5 alkylsulfonyl substituted by halogen,
•heterocyclyloxy,
•heterocyclyloxy substituted by substituent(s) independently selected from
the group consisting of:

828
••halogen,
••nitro,
••hydroxy,
••carboxy,
••carbamoyl,
••cyano,
—amino,
"Cj.5 alky],
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••halogen,
•••hydroxy,
•••carboxy, and
•••carbamoyl,
••C1-5alkoxy, and
••C1-5 alkoxy substituted by halogen,
•mono-C1-5 alkylamino.
•di-C1-5 alkylamino,
•mono-carbocycltc arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•C1-5 alkylcarbonylamino,
•C[.5alkylthio,
•C7.5 alkenylthio,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by halogen,
•carbocyctic arylthio substituted by C^ alkoxycarbonyl,
•heterocyclylthio,
•heterocyclylthio substituted by C1-5 alkyl,

829
•C1-5 alkylsulfinyl,
•C1-5 alkylsulfonyl,
•carbocyclic arylsulfinyl,
•carbocyclic aryjsulfinyl substituted by halogen,
•carbocyclic arylsulfonyl,
•carbocychc arylsulfonyl substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
••C1-5 alkoxy,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
■C1-5 alkoxycarbonyl,
•C1-5 alkoxycarbonyl substituted by carbocyclic aryl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,
••C1-5 alkyl,
••C1-5 alky! substituted by halogen,
••C1-5 alkoxy, and
"C1-5 alkoxy substituted by halogen,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C1-5 alkyl,
••C1-5 alkyl substituted by halogen,

830
"C1-5 alkoxy, and
"C1-5 alkoxycarbonyl;
R2 is selected from the group consisting of:
hydrogen, halogen, hydroxy, carboxy, carbamoyl, amino, C1-5 alkyl, C1-5
alkyl substituted by halogen, C1-5 alkyl substituted by hydroxy, C1-5 alkyl
substituted by carboxy, C1-5 alkyl substituted by carbamoyl, C1-5 alkoxy, C1-5
alkoxy substituted by halogen, -NHNH2, -NHNHBoc, -N(R2a)(R2b), morpholino, 4-
acetyl-piperazyl, or 4-phenyl-piperazyI,
wherein R2a is hydrogen or C1-5 alkyl and R2b is C1-5 alkyl, C3,6 cycloalkyl, or C1-5
alkyl substituted by substituent(s) independently selected from the group
consisting of:
•halogen,
•hydroxy,
•carboxy,
•carbamoyl,
•C1-5 alkoxy,
•amino,
•-NHBoc,
•C3-6 cycloalkyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl,
••C1-5 alkoxy, and
••-SO2NH2,
•heterocyclyl, and

831
C3-6 cycloalkyl, carbocyclic aryl, carbocyclic aryl substituted by substituent(s)
independently selected from the group consisting of:
•halogen,
•C1-5 alkyl,
•C1-5 alkoxy, and
•a group of Formula (V):

wherein Boc is carbamic acid tert-butyl ester and G is C1-5 alkyl or C1-5 alkyl
substituted by substituent(s) independently selected from the group consisting of:
•carbocyclic aryl,
•halogenated carbocyclic aryl, and
•carbocyclic aryl substituted by C1-5 alkoxy;
or R2 is methylamino or dimethylamino when Q is Formula (II) and Y is a single
bond or -CH2-;
Each T is independently selected from the group consisting of halogen, hydroxy,
carboxy, carbamoyl, amino, cyano, nitro, C1-5 alkyl, C1-5 alkyl substituted by
halogen, C1-5 alkyl substituted by hydroxy, d-5 alkyl substituted by carboxy, C1-5
alkyl substituted by carbamoyl, C2.5 alkenyl, C2-5 alkynyl, C3-6 cycloalkyl, C1-5
alkoxy, C1-5 alkoxy substituted by halogen, carbocyclic aryl, heterocyclyl, and
-N(R2a)(R2b);
pisO, 1,2, 3, 4 or 5;
L is selected from the group consisting of Formulae (VI) to (XXI):

832

wherein R3 and R4 are independently hydrogen or C1-5 alkyl; and A and B are
independently a single bond, -CH2-, or -(CH?):-;
and

833
Y represents;
(i) -C(O)NR5-, -C(S)NR5-, -C(0)0-, -S(0)2-, -C(0)-, -C(S)-, a single bond, or
-CH2- when L is selected from the group consisting of Formulae (VI) to
(XIII); or
(ii) -C(O)NR5-, -C(S)NR5-, -C(O)O- or -OC(O)- when L is selected from the
group consisting of Formulae (XIV) to (XXI);
wherein R5 is hydrogen or C1-5 alkyl, or when Y is -C(O)NR5- then R5 and R!
together with the nitrogen they are bonded form a heterocyclyl group;
wherein carbocyclic aryl is phenyl, naphthyl, anthranyl, phenanthryl, or
biphenyl;
carbocyclyl is 10,ll-dihydro-5-oxo-dibenzo[a,d]cyC1-5heptyl, 1-oxo-
indanyl, 7,7-dimethyl-2-oxo-bicyclo[2.2.1]heptyl, 9//-fluorenyl, 9-oxo-fluorenyl,
acenaphthyl, anthraquinonyl, C-fluoren-9-ylidene, indanyl, indenyl, 1,2,3,4-
tetrahydro-naphthyl, or bicyclo[2.2.1]heptenyl;
heterocyclyl is 1,2,3,4-tetrahydro-isoquinolyl, 1,2,3-thiadiazolyl, 1,2,3-
triazolyl, l,2-dihydro-3-oxo-pyrazolyl, 1,3,4-thiadiazolyI, 1,3-dioxo-isoindolyI,
1,3-dioxolanyl, l//-indolyl, l/7-pyrrolo[2,3-c]pyridyl, l#-pyrrolyl, l-oxo-3//-
isobenzofuranyl, 2,2',5',2"-terthiophenyl, 2,2'-bithiophenyl, 2,3-dihydro-l-oxo-
isoindolyl, 2,3-dihydro-benzo[l,4]dioxinyl, 2,3-dihydro-benzofuryl, 2,4-dihydro-3-
oxo-pyrazolyl, 2//-benzopyranyl, 2-oxo-benzopyranyl, 2-oxo-pyrroltdinyl, 3,4-
dihydro-2f/'-benzo[l,4]oxazinyl, 3,4-dihydro-2//-benzo[b][l,4]dioxepinyl, 4H-
benzo[l,3]dioxinyl, 4//-benzopyranyI, 4-oxo-l,5,6,7-tetrahydro-indoIyl, 4-oxo-
3,4-dihydro-phthalazinyl, 4-oxo-benzopyranyl, 9,10,10-trioxo-thioxanthenyl, 9H-
carbazolyl, 9//-xanthenyl, azetidinyl, benzimidazolyl, benzo[l,3]dioxolyl,
benzo[2,l,3]oxadiazolyl, benzo[l,2,5]oxadiazolyl, benzo[b]thienyl, benzofuryl,
benzothiazolyl, cinnolyl, furyl, imidazo[2,l-b]thiazolyl, imidazolyl, isoxazolyl,
morpholino, morpholinyl, oxazolyl, oxolanyl, piperazyl, piperidyl, piridyl,

834
pyrazolo[5,l-b]thiazolyl, pyrazolyl, pyraziny], pyridyl, pyrimidyl, pyrrolidyl,
quinolyl, quinoxalyl, thiazolidyl, thiazolyl, thienyl, thiolanyl, 2,3-dihydro-
benzofuryi, tetrahydro-thienyl, or benzofuranyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
2. The compound according to claim 1 wherein Ri is selected from the group consisting of:
(i) Ci_8 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•oxo,
•C1-5 alkoxy,
•Cj.5 alkoxy substituted by carbocyclic aryl,
•C1-5 alkylcarbonyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••nitro,
••C1-5 alkyl, and
■•C1-5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by C1-5 alkyl,
•Cj.5 alkoxycarbonyl,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylamino,

835
•mono-C1-5 alkylamino substituted by cyano,
•mono-do aikylamino substituted by carbocyciic aryl,
•di-Cj.5 alkylamino,
•di-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino substituted by carbocyciic aryl,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•mono-carbocyclic arylamino substituted by d-5 alkyl,
•di-carbocyclic arylamino,
•di-carbocyclic arylamino substituted by halogen,
•di-carbocyclic arylamino substituted by d-s alkyl,
•C1-5 alkoxycarbonylamino,
•carbocyciic arylcarbonylamino,
•carbocyciic arylsulfonylamino,
•carbocyciic arylsulfonylamino substituted d-5 alkyl,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by substituent(s) independently selected from
the group consisting of:
••carbocyciic aryl,
••carbocyciic aryl substituted by halogen, and
••carbocyciic aryl substituted by C1-5 alkoxy,
•carbocyciic aryithio,
•heterocyclylthio,
•heterocyclylthio substituted by nitro,
•heterocyclylthio substituted by d_5 alkyl,
•C3-6 cycloalkyl,
•C3-6 cycloalkenyl,
•carbocyclyl,

836
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
"C1-5 alkyl,
••Cj_5 alkoxy,
••C2-5 alkenyl, and
"C2-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••nitro,
••C1-5 alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••oxo,
•••carbocyclic aryl, and
•••heterocyclyl,
••C2-5 alkenyl,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by halogen,
••C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryloxy,
••mono-carbocyclic arylaminocarbonyl,

837
••mono-carbocyclic arylaminocarbonyl substituted by halogen,
••di-carbocyclic arylaminocarbonyl,
—di-carbocyclic arylaminocarbonyl substituted by halogen,
••carbocyclic aryl, and
••heterocyclyl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•■d.s alkyl,
••C1-5 alkyl substituted by carbocyclic aryl,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by carbocyclic aryl,
"carbocyclic aryl, and
"carbocyclic aryl substituted by halogen,
(ii) C2-7 alkenyl, and
C2-7 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
••C1-5 alkoxy,
(iii) C2-5 alkynyl, and
C2-5 alkynyl substituted by carbocyclic aryl,
(iv) C3-12 cycloalkyl, and
C3.12 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:

838
•do alkyl,
•C1-5 alkyl substituted by oxo,
•C1-5 alkyl substituted by carbocyclic aryl, and
•carbocyclic aryl,
(v) carbocyclyl,
(vi) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
•carboxy,
•carbamoyl,
•Ci-io alkyl,
•CLIO alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••hydroxy,
••oxo,
••carbocyclic aryloxy,
••carbocyclic aryl, and
"•carbocyclic aryl substituted by Cj.5 alkyl,
•C1-7 alkoxy,
•C1-7 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••carbocyclic aryl, and

839
••halogenated carbocyclic aryl,
•C2.5 alkenyloxy,
•C3-6 cycloalkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by nitro,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•C1-5 alkoxycarbonyl,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•amino,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino substituted by cyano,
•C2.5 alkynylcarbonylamino,
•C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,
•Ci_s alkoxycarbonylamino,
•(carbocyclic aryl)NHC(O)NH,
•(carbocyclic aryI)NHC(O)NH substituted by C1-5 alkoxy,
•(carbocyclic aryl)NHC(O)NH substituted by haloganated C1-5 alkoxy,
•carbocyclic aryl azo,
•carbocyclic aryl azo substituted by mono-C1-5 alkylamino,
•carbocyclic aryl azo substituted by di-C1-5 alkylamino,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by halogen,
•carbocyclic arylthio,

840
•carbocyclic arylthio substituted by nitro,
•carbocyclic arylthio substituted by cyano,
•aminosulfonyl,
•mono-C1-5 alkylaminosulfonyl,
•di-C1-5 alkylaminosulfonyl,
•heterocyciylsulfonyl,
•C3-6 cycloalkyl,
•C3-6 cycloalkyl substituted by C1-5 alkyl,
•carbocyclic aryl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5 alkyl,
••carbocyclic aryj, and
••halogenated carbocyclic aryl,
(vii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•amino,
•hydroxy,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••hydroxy,
••C1-5 alkylthio,

841
•*C1-5 alkylthio substituted by carbocyclic aryl,
'•C1-5 alkylthio substituted by halogenated carbocyclic aryl,
••carbocyclic aryl,
••carbocyclic aryl substituted by halogen, and
••heterocyclyl,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C1-5 alkyl,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-C|.5 alkylamino,
•di-C1-5 alkylamino,
•C1-5 alkylthio,
•C7-5 alkenylthio,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by C1-5 alkoxycarbonyl,
•C1-5 alkylsulfonyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by C1-5 alkyl,
•C1-5 alkoxycarbonyl,
•C1-5 alkoxycarbonyl substituted by carbocyclic aryl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,
"C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,

842
•heterocyclyl;
wherein carbocyclic aryl is phenyl, naphthyl, or anthranyl;
carbocyclyl is 1,2,3,4-tetrahydronaphthyl, 1-oxo-indanyl, 9-fluorenyl, 9H-
fluorenyl, 9-oxo-977-fluorenyl, adamantly, bicyclo[2.2.1]heptenyl,
bicyclo[2.2.1]heptyl, indanyl, indenyl, or menthyl;
heterocyclyl is 1,2,3-triazolyI, \H-'mdo\y\, 1/7-pyrrolyl, 2,3-dihydro-l-
oxo-isoindolyl, 2,3-dihydro-benzo[l,4]dioxinyl, 2,3-dihydro-benzofuryl, 2,4-
dihydro-3-oxo-pyrazolyl, 2//-benzopyranyI, 2-oxo-benzopyranyl, 3,4-dihydro-2//-
benzo[b][l,4]dioxepinyl, 4,5,6,7-tetrahydro-benzo[b]thienyl, 4H-
benzo[l,3]dioxinyl, 4-oxo-l,5,6,7-tetrahydro-indolyl, 4-oxo-benzopyranyl, 9H-
carbazolyl, 9//-xanthenyl, azetidinyl, benzo[l,3]dioxolyl, benzo[2,l,3]oxadiazolyl,
benzo[l,2?5]oxadiazolyl, benzo[2,l,3]thiadiazolyl, benzo[b]thienyl, benzofuryl,
benzothiazolyl, furyl, imidazo[2,l-b]thiazolyl, imidazolyl, isoxazolyl, morpholino,
morpholinyl, oxazolyl, phenanthro[9,10-d]oxazolyl, piperidyl, pyrazolyl, pyridyl,
pyrimidyl, quinolyl, quinoxaly!, tetrahydrofuryl, thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
3. The compound according to claim 2 wherein Q is Formula (II);
R, is selected from the group consisting of:
(i) Ci-8 alkyl, and
Ci-8 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•C1-5 alkylcarbonyloxy,

843
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by nitro,
•heterocyclyloxy,
•heterocyclyloxy substituted by C1-5 alkyl,
•C1-5 alkoxycarbonyl,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•mono-C1-5 alkylamino substituted by carbocyclic aryl,
•di-C1-5 alkylamino,
•di-Q.5 alkyiamino substituted by cyano,
•di-C1-5 alkylamino substituted by carbocyclic aryl,
•mono-carbocyclic arylamino,
•di-carbocyclic arytamino,
•C1-5 alkoxycarbonylamino,
•carbocyclic arylcarbonylamino,
•carbocyclic aryisulfonylamino,
•carbocyclic aryisulfonylamino substituted C1-5 alkyl,
•C1-5 alkylthio,
•Ci.s alkylthio substituted by substituent(s) independently selected from
the group consisting of:
••carbocyclic aryl,
"carbocyclic aryl substituted by halogen, and
"carbocyclic aryl substituted by C1-5 alkoxy,
•carbocyclic arylthio,
•heterocyclylthio,

844
•heterocyclylthio substituted by C1-5 alkyl,
•C3-6 cycloalkyl,
•C3-6 cycloalkenyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C,_5 alkyl,
••C1-5 alkoxy,
•*C2-5 alkenyl, and
••C2-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••nitro,
••C1-5 alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••oxo,
•••carbocyclic aryl, and
•••heterocyclyl,
••C2-5 alkenyl,
••C1-5 alkoxy,

845
••C1-5 alkoxy substituted by halogen,
••Q.5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryloxy,
—mono-carbocyclic arylaminocarbonyl,
••mono-carbocyclic arylaminocarbonyl substituted by halogen,
—di-carbocyclic arylaminocarbonyl,
••di-carbocyclic arylaminocarbonyl substituted by halogen,
••carbocyclic aryl, and
••heterocyclyl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
-C.5 alkyl,
••C1-5 alkyl substituted by carbocyclic aryl,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryl, and
"carbocyclic aryl substituted by halogen,
(ii) C2-7 alkenyl, and
C2-7 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
•"C1-5 alkoxy,
(iii) C2-5 alkynyl, and

846
C2-5 alkynyl substituted by carbocyclic aryl?
(iv) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:
•C1-5 alky!,
•C1-5 alkyl substituted by oxo,
•C1-5 alkyl substituted by carbocyclic aryl, and
•carbocyclic aryl,
(v) carbocyclyl,
(vi) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••oxo,
••carbocyclic aryloxy,
••carbocyclic aryl, and
••carbocyclic aryl substituted by C1-5 alkyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen,

847
••carbocyclic aryl, and
••halogenated carbocyclic aryl,
•C2-5 alkenyloxy,
•C3-6 cycloalkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•C1-5 alkoxycarbonyl,
•mono-C1-5 alkylaminocarbonyl,
•di-Cj.5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbony! substituted by carbocyclic aryl,
•amino,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino substituted by cyano,
•C2-5 alkynylcarbonylamino,
•C7.5 alkynylcarbonylamino substituted by carbocyclic aryl,
•(carbocyclic aryI)NHC(O)NH,
•(carbocyclic aryl)NHC(O)NH substituted by C1-5 alkoxy,
•(carbocyclic ary!)NHC(O)NH substituted by haloganated C1-5 alkoxy,
•C1-5 alkylthio,
*C1-5 alkylthio substituted by halogen,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by cyano,
•mono-C1-5 aikylaminosulfonyl,
•di-C1-5 aikylaminosulfonyl, and
•carbocyclic aryl,

848
(vii) heterocyclyl, and
heterocycly] substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••hydroxy,
»C1-5 alkylthio,
••Cj-s alkylthio substituted by carbocyclic aryl,
••C1-5 alkylthio substituted by halogenated carbocyclic aryl,
••carbocyclic aryl,
••carbocyclic aryl substituted by halogen, and
••heterocyclyl,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkyl,
•C1-5 alkylthio,
•C2.5 alkenylthio,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by C1-5 alkoxycarbonyl,
•C1-5 alkylsulfonyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by C1-5 alkyl,
•C1-5 alkoxycarbonyl,
•carbocyclic aryl,

849
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
—halogen,
••nitro,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
•heterocyclyl;
R2 is methylamino or dimethylamino when Y is a single bond or -CH2-;
wherein carbocyclic aryl is phenyl, naphthyl, or anthranyl;
carbocyclyl is 1,2,3,4-tetrahydronaphthyl, 1-oxo-indanyl, 9-fluorenyl, 9-
oxo-9//-fluorenyl, bicyclo[2.2.1]heptyl, indenyl, or menthyl;
heterocyclyl is 1,2,3-triazolyl, l/f-indolyl, 177-pyrrolyI, 2,3-dihydro-l-
oxo-isoindolyl, 2,3-dihydro-benzo[l,4]dioxinyl, 2,3-dihydro-benzofuryl, 2,4-
dihydro-3-oxo-pyrazoIyl, 2//-benzopyranyl, 2-oxo-benzopyranyl, 3,4-dihydro-2//-
benzo[b][l,4]dioxepinyl, 4-oxo-benzopyranyl, 9#-carbazolyl, 9//-xanthenyI,
azetidinyl, benzo[l,3]dioxolyl, benzo[2,l,3]oxadiazolyl, benzo[l,2,5]oxadiazolyl,
benzo[b]thienyl, benzofuryl, benzothiazolyl, furyl, imidazo[2,l-b]thiazolyl,
imidazolyl, isoxazolyl, morpholino, pyrazolyl, pyridyl, pyrimidyi, quinolyl,
quinoxalyl, thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
4. The compound according to claim 3 wherein Ri is selected from the group consisting of:
(i) Ci-7 alkyl, and
C]_7 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•Cj_5 alkoxy,
•Cj.5 alkoxy substituted by carbocyclic aryl,

850
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•mono-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by substituent(s) independently selected
from the group consisting of:
••cyano, and
••carbocyclic aryl,
•di-Ci.s alkylamino,
•di-C1-5 alkylamino substituted by substituent(s) independently selected
from the group consisting of:
••cyano, and
••carbocyclic aryl,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted by C1-5 alkyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,
••Ci_g alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
••*oxo, and
•••carbocyclic aryl,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by halogen,

851
•heterocyclyl,
•heterocyclyl substituted by carbocyclic aryl, and
•heterocyclyl substituted by halogen,
(ii) C2.7 alkenyl, and
C2-7 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by C1-5 alkoxy,
(iii) C2-5 alkynyl, and
C2.g alkynyl substituted by carbocyclic aryl,
(iv) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:
•C1-5 alkyl, and
•C1-5 alkyl substituted by carbocyclic aryl,
(v) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•cyano,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••carbocyclic aryl,

852
—carbocyclic aryl substituted by halogen,
•C?-5 alkenyloxy,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino substituted by cyano,
•C1-5 alkylthio., and
•C1-5 alkylthio substituted by halogen,
(vi) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••hydroxy, and
••carbocyclic aryl,
•C1-5 alkoxy,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by C1-5 alkoxycarbonyl,
•C1-5 alkoxycarbonyl,
•carbocyclic aryl,
'carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
L is Formula (VII);

853
Y is a single bond or -CH2-;
R2 is methylamino or dimethylamino;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is \H-'mdo\y\, l//-pyrrolyl, 2,3-dihydro-benzo[l,4]dioxinyl,
4-oxo-benzopyranyI, 9/f-carbazolyl, azetidinyl, benzo[l,3]dioxolyl,
benzo[b]thienyl, furyl, imidazo[2,l-b]thiazolyl, pyrazolyl, pyridyl, orthienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
5. The compound according to claim 4 wherein p is 0; R3 and R4 are hydrogen; A is a single
bond or -CH2-; and B is a single bond or -CH2-;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
6. The compound according to claim 5 wherein Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•mono-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino,
•di-C1-5 alkylamino substituted by cyano,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
"C1-5 alkoxy,

854
•heterocyclyl, and
•heterocyclyl substituted by carbocyclic aryl,
(ii) C2-5 alkenyl, and
C2-5 alkenyl substituted by carbocyclic aryl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by halogen, and
•C2.5 alkenyloxy,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5alkyl,
•C1-5 alkyl substituted by carbocyciic aryl,
•C1-5 alkoxy, and
•C1-5 alkoxycarbonyl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is l/f-indolyl, azetidinyl, or benzo[l,3]dioxolyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceuticaliy acceptable salt, hydrate, or solvate thereof.
7. The compound according to claim 1 selected from the group consisting of:
ethyl 4,6-dichloro-3-{[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)amino]methyl}-lH-indole-2-carboxyIate;

855
3-[{2-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
amino]ethyl}(phenyl)amino]propanenitrile;
N4,N4-dimethyl-N2-(cis-4-{[2-(2-phenyl-lH-indoI-3-yl)ethy]]amino}-
cyclohexyl)quinoline-2,4-diamine;
N2-[cis-4-({[l-(diphenylmethyl)azetidin-3-yI]methyI}amino)cyclohexyl]-N4,N4-
dimethylquinoline-2,4-diamine;
N2-(cis-4-{[(2,6-dimethoxybenzyl)amino]methyi}cyclohexyl)-N4,N4-
dimethylquinoline-2,4-diamine;
N2-(cis-4-{[(2-ethoxybenzyl)amino]methyl}cyC1-5hexyl)-N4,N4-dimethylquinoline-
2,4-diamine;
N2-[cis-4-({[(4-methoxy-l-naphthyl)methyl]amino}methyI)cyC1-5hexyl]-N4,N4-
dimethylquinoline-2,4-diamine;
4-bromo-2-({[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-
methyl]amino}methyI)-6-methoxyphenol;
N2-[cis-4-({[(5-bromo-lH-indol-3-yI)methyl]amino}methyl)cyclohexyI]-N4,N4-
dimethylquinoline-2,4-diamine;
N2-(cis-4-{[(5-bromo-2,4-dimethoxybenzyl)amino]methyI}cyC1-5hexyI)-N4,N4-
dimethytquinoline-2,4-diamine;
N2-(cis-4-{[(3,3-diphenylprop-2-en-l-yl)amino]methyl}cyclohexyl)-N4,N4-
dimethylquinoline-2,4-diamine;
N4,N4-dimethyl-N"-(cis-4- {[(2,4,6-trimethoxybenzyl)amino]methyl} -
cyclohexyl)quinoline-2,4-diamine;
N2-(cis-4-{[(2,5-diethoxybenzyl)amino]methyl}cyC1-5hexyl)-N4,N4-
dimethylquinoline-2,4-diamine;
N2-(cis-4-{[(2,4-diethoxybenzyI)amino]methyl}cyclohexyI)-N4,N4-
dimethylquinoline-2,4-diamine;
N2-(cis-4-{[(3,5-dibromo-2-methoxybenzyl)amino]methyI}cyclohexyl)-N4,N4-
dimethylquinoline-2,4-diamine;

856
N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-triethoxybenzyl)amino]methyI}-
cyclohexyl)quinoline-2,4-diamine;
N4,N4-dimethyi-N2-(cis-4-{[(2,4,5-trimethoxybenzyI)amino]methyl}-
cyclohexyl)quinoIine-2,4-diamine;
N2-[cis-4-({[2-(al]yloxy)benzyl]amino}methyl)cyC1-5hexyI]-N4,N4-
dimethylquinoline-2,4-diamine;
N2-[cis-4-({[(7-methoxy-l,3-benzodioxol-5-yI)methyI]amino}methyl)-
cyclohexyl]-N4,N4-dimethylquinoline-2,4-diamine;
N2-{cis-4-[2-(4-bromo-2-trifIuoromethoxy-pheny])-ethylamino]-cyclohexyl}-
N4,N4-dimethyl-quinoline-2,4-diamine;
N2-[cis-4-(4-bromo-2-trifluoromethoxy-benzyl)amino-cyclohexyl]-N4,N'1-
dimethyI-quinoline-2,4-diamine;
N -[cis-4-(4-bromo-2-trifluoromethoxy-benzyI)arnino-cyclohexyl]-N4-methyl-
quinoline-2,4-diamine;
N2-{4-[2-(4-bromo~2-trifluoromethoxy-phenyl)-ethylamino]-cyclohexyl}-N4-
methyl-quinoline-2T4-diamine;
N4-methyI-N2-{cis-4-[(2-trifluoromethoxy-benzyl)amino-methyl]-cyclohexyI}-
quinoIine-2,4-diamine;
N2-{cis-4-[(4-bromo-2-trifluoromethoxy-benzyl)amino-methyl]-cyclohexyl}-N4-
methyl-quinoIine-2,4-diamine;
N -{cis-4-[(4-bromo-2-trifluoromethoxy-benzyl)amino-methyl]-cyclohexyl}-
N4,N4-dimethyI-quinoline-2,4-diamine;
N4,N4-dimethyl-N2-{cis-4-[(2-trifluoromethoxy-benzyl)amino-methyl]-
cyclohexyl}-quinoline-2,4-diamine;
cis-N-(3,5-dimethoxybenzyl)-N'-(4-methylquinoiin-2-yl)cyclohexane-I,4-diamine;
and
cis-N-(3,5-dichlorobenzyl)-N'-(4-methylquinolin-2-yl)cyC1-5hexane-l,4-diamine;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.

857
8. The compound according to claim 3 wherein R] is selected from the group consisting of:
(i) C1-5 alkyl, and
C].g alkyl substituted by substituent(s) independently selected from the
group consisting of:
•hydroxy,
•oxo,
•C\.5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•C1-5 alkylcarbonyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••nitro,
••C1-5 alkyl,
••C1-5 alkoxy, and
"C1-5 alkoxy substituted by halogen,
•heterocyclyloxy,
•heterocyclyloxy substituted by C1-5 alkyl,
•mono-C1-5 alkylaminocarbony!,
•di-C]-5 alkylaminocarbonyl,
•mono-C1-5 alkylamino,
•di-Cjo alkylamino,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•di-carbocyclic arylamino substituted by halogen,

858
•carbocyclic arylcarbonylamino,
•C1-5 alkoxycarbonylamino,
•C1-5 alkylthio,
•Cj.5 alkylthio substituted by substituent(s) independently selected from
the group consisting of:
••carbocyclic aryl, and
"•carbocyclic aryl substituted by substituent(s) independently
selected from the group consisting of:
•••halogen, and
•••C1-5 alkoxy,
•carbocyclic arylthio,
•heterocyclylthio,
•heterocyclylthio substituted by C1-5 alky!,
•C3-6 cycloalkyl,
•C3-6 cycloalkenyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C1-5 alkyl,
••C1-5 alkoxy,
••C2-5 alkenyl, and
••C7-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulflnyl,
•carbocyclic aryl,

859
•carbocyclic aryi substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
"hydroxy,
••nitro,
■•C ]_5 alky I,
••C1-5 alky! substituted by substituent(s) independently selected
from the group consisting of:
•••oxo,
•••carbocyclic aryl, and
•••heterocyclyl,
"C1-5 alkoxy,
••C1-5 alkoxy substituted by halogen,
"C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryloxy,
••mono-carbocyclic arylaminocarbonyl,
••mono-carbocyclic arylaminocarbonyl substituted by halogen,
••di-carbocyclic arylaminocarbonyl,
••di-carbocyclic arylaminocarbonyl substituted by halogen,
••carbocyclic aryl, and
"heterocyclyl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5alkyl,
•"C1-5 alkyl substituted by carbocyclic aryl,
••C1-5 alkoxy,
"C1-5 alkoxy substituted by carbocyclic aryl,

860
••carbocyclic aryl, and
••carbocyclic aryl substituted by halogen,
(ii) C2-5 alkenyl, and
C2o alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
••nitro,
(iii) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••oxo, and
••carbocyclic aryl, and
•carbocyclic aryl,
(iv) carbocyclyl,
(v) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
•carboxy,

861
•carbamoyl,
•Ci-salkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••hydroxy,
••oxo,
••carbocyclic aryloxy,
••carbocyclic aryl, and
••carbocyclic aryl substituted by C1-5 alkyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•C1-5 alkoxycarbonyl,
•mono-C1-5 alkylamtnocarbonyl,
•di-Ci,s alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-Cu alkylaminocarbonyl substituted by carbocyclic aryl,
•amino,
•mono-C1-5 alkylamino,
•di-C],5 alkylamino,
•C2-5 alkynylcarbonylamino,
•C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,
•(carbocyclic aryi)NHC(O)NH,

862
•(carbocyclic aryl)NHC(O)NH substituted by C1-5 alkoxy,
•(carbocyclic aryl)NHC(O)NH substituted by haloganated C1-5 alkoxy,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by halogen,
•carbocyclic arylthio,
•carbocyciic arylthio substituted by cyano,
•mono-C1-5 alkylaminosulfonyl,
•di-Cj-5 alkylaminosulfonyl, and
•carbocyclic aryl,
(vi) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•hydroxy,
•amino,
•Ci.jalkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
"halogen,
••C1-5 alkylthio,
"C1-5 alkylthio substituted by carbocyclic aryl,
••C1-5 alkylthio substituted by halogenated carbocyclic aryl,
••carbocyclic aryl,
••carbocyclic aryl substituted by halogen, and
••heterocyclyl,
•C1-5 alkoxy,
•carbocyclic aryloxy,

863
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C1-5 alky],
•carbocyclic aryloxy substituted by Cu alkoxy,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•C1-5 alkylthio,
•C2-5 alkenylthio,
•carbocyclic arylthio,
•C1-5 alkylsulfonyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by C1-5 alkyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
-d.s alkyl,
•heterocyclyl;
L is Formula (VII);
Y is -C(O)-;
wherein carbocyclic aryl is phenyl, naphthyl, or anthranyl;
carbocyclyl is 1,2,3,4-tetrahydronaphthyl, 1-oxo-indanyl, 9-oxo-9H-
fluorenyl, or indenyl;
heterocyclyl is 1,2,3-triazolyl, \H-mdo\y\, 1/f-pyrrolyl, 2,3-dihydro-l-
oxo-isoindolyl, 2,3-dthydro-benzofuryl, 2,4-dihydro-3-oxo-pyrazolyl, 2H-
benzopyranyl, 2-oxo-benzopyranyl, 9//-xanthenyl, benzo[l,3]dioxolyl3
benzo[2,l,3]oxadiazolyl, benzo[l,2,5]oxadiazolyl, benzo[b]thienyl, benzofuryl,

864
benzothiazolyl, furyl, imidazolyl, isoxazolyl, morpholino, pyrazolyl, pyridyl,
pyrimidy!, quinolyl, quinoxalyl, thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
9. The compound according to claim 8 wherein R2 is hydrogen, halogen, methyl,
trifluoromethyl, methoxy, carbamoyl, amino, methylamino, or dimethyl ami no; p is 0; R3
and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
10. The compound according to claim 9 wherein Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•oxo,
•carbocyciic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyciic aryloxy substituted by C1-5 alkyl,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•di-carbocyc!ic arylamino substituted by halogen,
•C3-6 cycloalkyl,
•carbocyclic aryl,

865
•carbocyclic aryl by substituent(s) independently selected from the group
consisting of:
••halogen,
••C1-5 alkyl, and
••C1-5 alkoxy,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
»C1-5 alkyl,
••C1-5 alkoxy, and
••carbocyclic aryl,
(ii) C2-3 alkenyl, and
C2.5 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
••nitro,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
•carbamoyl,
•C].s alkyl,

866
•C1-5 alkyl substituted by halogen,
•C1-5 alkyl substituted by hydroxy,
•C1-5 alkoxycarbonyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••carbocyclic aryl,
•carbocyclic aryloxy, and
•carbocyclic aryloxy substituted by C1-5 alkoxy,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•amino,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C1-5 alkyl,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-Cj.5 alkylamino,
•di-C1-5 alkylamino,
•carbocyclic aryl,
•carbocyclic aryl substituted by halogen,
•carbocyclic aryl substituted by nitro, and

867
•heterocyclyl;
wherein carbocyclic ary] is phenyl;
heterocyclyl is 1,2,3-triazolyl, l//-indolyl, \H-pyno\y\, 9//-xanthenyl,
benzo[2,l,3]oxadiazoiyl, benzo[l,2,5]oxadiazolyl, furyl, isoxazolyl, pyridyl,
quinolyl, quinoxalyl, thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
11. The compound according to claim 10 wherein R\ is selected from the group consisting of:
(i) C1-5 alkyl, and
Cj-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryioxy substituted by C1-5 alkyl,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-C1-5 alkylamino,
•di-Cj.5 alkylamino,
•mono-carbocyclic arylamino,
•di-carbocychc arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•di-carbocyclic arylamino substituted by halogen,
•carbocyclic aryl,
•carbocyclic aryl by substituent(s) independently selected from the group
consisting of:
••halogen,
"C1-5 alkyl, and
••C1-5 alkoxy,

868
and
•heterocyclyl,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•nitro,
•hydroxy,
•cyano,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxycarbonyl,
•C1-5 alkoxy,
•Cj-5 alkoxy substituted by halogen,
•carbocyclic aryloxy, and
•carbocyclic aryloxy substituted by C1-5 alkoxy,
(iii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C^ alkyl,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•carbocyclic aryl,
•carbocyclic aryl substituted by halogen,

869
■carbocyclic aryl substituted by nitro, and
•heterocyclyl;
wherein carbocyclic aryl is phenyl;
heterocyclyl is 1/f-indolyl, lif-pyrrolyl, 9#-xanthenyl,
benzo[2,l,3]oxadiazolyl, benzo[l,2,5]oxadiazolyl, furyl, isoxazolyl, pyridyl,
thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
12. The compound according to claim 1 selected from the group consisting of:
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-
methoxybenzamide;
3-bromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
benzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2,l,3-
benzoxadiazoIe-5-carboxamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-
benzamide;
4-chloro-N-(cis-4-{[4-{dimethylamino)quinolin-2-y]]amino}cyclohexyl)-
benzamide;
4-chloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-
nitrobenzamide;
3-cyano-N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexyl)-
benzamide;
3,5-dichloro~N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)benzamide;

870
3,4-dichloro-N-(cis-4-{[4-(dimethyIamino)quinolin-2-yi]amino}-
cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-2,2-
diphenylacetamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3,4-
difluorobenzamide;
N-(cis-4-{[4-(dimethy!amino)quinolin-2-yl]amino}cyclohexyl)-3,5-
difluorobenzamide;
N-(cis-4-{[4-(dimethyIamino)quinoIin-2-yl]amino}cyclohexyl)-4-
fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-fluoro-5-
(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-methyl-3-
nitrobenzamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyI)-3-nitrobenzamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-
phenoxybutanamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
phenoxypropanamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyC1-5hexy!)-3-
methylbenzamide;
N-(cis-4-{[4-(dimethyIamino)quinoIin-2-yl]amino}cyclohexyl)-3-
(trifluoromethoxy)benzamide;
4-bromo-N-(cis-4-{[4-(dimethytamino)quinolin-2-yl]amino}cyC1-5hexyl)-3-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyI)-3-iodobenzamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2,4-
difluorobenzamide;

871
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2,5-dimethyl-3-
furamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-4-
fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-3-fluoro-4-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-3,5-
dimethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3,5-
bis(trifluoromethyl)benzamide;
(2E)-N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-3-(4-
nitrophenyl)acrylamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-fluoro-3-
methylbenzamide;
2,5-dichloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}-
cyc!ohexyl)thiophene-3-carboxamide;
2-(4-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)acetamide;
3-(2-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyI)-5-methylisoxazole-4-carboxamide;
l-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)cyclopentanecarboxamide;
3-(2-chloro-6-fluorophenyI)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
y!]amino}cyclohexyl)-5-methyIisoxazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyC1-5hexyl)-3-
fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-fluoro-3-
(trifluoromethyl)benzamtde;

872
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-5-methyl-2-
phenyl-2H-l,2,3-triazole-4-carboxamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-(4-
methoxyphenoxy)-5-nitrobenzamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyC1-5hexyl)-5-nitro-2-
furamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyI)-2-
phenoxyacetam i de;
N-(cis-4-{[4-(dimethylamir\o)quinolin-2-yl]amino}cyC1-5hexyI)quinoxaline-2-
carboxamide;
2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)acetamide;
3-(2,6-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)-5-methyIisoxazoIe-4-carboxamide;
N-(cis-4- {[4-(dimethyIamino)quinolin-2-yI]amino} cyclohexyl)-2-
phenoxynicotinamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-(4-
methylphenoxy)nicotinamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-2-(2-thienyl)-l,3-
thiazoIe-4-carboxamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-
thiophene-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-(2,3,6-
trichlorophenyl)acetamide;
5-(4-chIoro-2-nitrophenyl)-N-(cis-4-{[4-(dimethyIamino)quinolin-2-
yl]amino}cyC1-5hexyl)-2-furamide;
5-chloro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-
thiophene-2-carboxamide;

873
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-5-iodo-2-furamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-2-(2-
iodophenyl)acetamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-2-(5-methoxy-2-
methyl-lH-indol-3-yl)acetamide;
(2E)-N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyI)-3-(3-
nitrophenyl)acryl amide;
2,2-bis(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]-
amino}cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-5-nitrothiophene-
2-carboxamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-methyl-4-
nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-3-methoxy-4-
nitrobenzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
furamide;
4,5-dibromo-N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}-
cyclohexy!)thiophene-2-carboxamide;
4,5-dibromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)-2-
furamide;
N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexy l)-2-( 1 H-indol-3-
yl)acetamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-y]]amino}cyclohexyl)-2-(lH-indol-3-yl)-
4-oxo-4 -pheny Ibutanam ide;
N-(cis-4-{[4-(dimethy!amino)quinolin-2-yl]amino}cyclohexyl)-2-(2-phenyl-lH-
indol-3-yl)acetamide;

874
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyI)-2-(2,4,6-
tri ch lorophenoxy)acetam ide;
3-(benzyloxy)-N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}-cyclohexyI)-4-
methoxybenzam ide;
N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexyl)-2-
phenoxybenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-2-phenylquinoIine-
4-carboxamide;
N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexy l)-5-(3 -nitrophenyl)-
2-furamide;
N-(cis-4-{[4-(dimethyiamino)quinoIin-2-yl]amino}cyC1-5hexyl)-5-nitrothiophene-
3-carboxamide;
N-(cis-4-{[4-(dimethylamino)quinolin'2-yl]amino}cyclohexyl)-l-methyl-4-nitro-
1 H-pyrrole-2-carboxamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-4-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-2-methoxy-4-
nitrobenzamide;
N-(cis-4-{[4-(dimethyIamino)quinoIin-2-yI]amino}cyclohexyl)-3-fluoro-4-
(trifl uoromethy I)benzam ide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3,5-dimethyI-4-
nitrobenzamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-mesityl-2-
oxoacetamide;
5-chIoro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
hydroxybenzam ide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)methyl]-3-
methoxybenzamide;

875
3-bromo-N-[(cts-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
methyljbenzamide;
4-bromo-N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-
methyl] benzam ide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)methyI]-2,I,3-
benzoxadiazoIe-5-carboxamide;
3-chloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
methyl]benzamide;
4-chloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-
methyl]benzamide;
4-chloro-N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-methyl]-
3-nitrobenzamide;
3-cyano-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
methyl]benzamide;
3,5-dichloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)methyl] benzam ide;
3,4-dichloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)methyl]benzamide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)methyl]-2,2-
diphenylacetamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-3,4-
difluorobenzamide;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)methyl]-3,5-
difluorobenzamide;
N-[(cis-4-{[4-(dimethyiamino)quinolin-2-yl]amino}cyclohexyl)methyl]-4-
fluorobenzamide;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyc]ohexyl)methyl]-3-fluoro-
5-(trifluoromethyI)benzamide;

876
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-4-methyl-
3-nitrobenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)methyl]-3-
nitrobenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)methyI]-2-
phenoxybutanamide;
N-[(cis-4-{[4-(d)methyIamino)quinolin-2-yl]amino}cyC1-5hexyl)methyl]-2-
phenoxypropanam ide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}cyclohexyl)methyl]-3-
methylbenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-3-
(trifluoromethoxy)benzamide;
4-bromo-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-methyl]-
3 -m ethy Ibenzam id e;
N-[(cis-4-{[4-(dimethylamino)quinotin-2-yl]amino}cyclohexyl)methyl]-3-
iodobenzamide;
3-chloro-N~[(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyI)-methy!]-
2,4-difIuorobenzamide;
N-[(cis-4-{[4-(dimethyIamino)quinoIin-2-yl]amino}cyclohexyl)methy!]-2,5-
dimethyl-3-furamide;
3-chloro-N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyI)-methyl]-
4-fluorobenzamide;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yI]amino}cyclohexyl)methyl]-3-fluoro-
4-methy Ibenzam ide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)methyI]-3,5-
dimethoxybenzaraide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-3,5-
b i s(trifluoromethy l)benzam ide;

877
(2E)-N-[(cis-4-{[4-(dimethyIamino)quinoIin-2-yl]amino}cyclohexyl)-methyl]-3-
(4-nitrophenyl)acrylamide;
N-[(cis-4-{[4-(dimethyIamino)quinoIin-2-yI]amino}cyclohexyl)methyl]-4-fiuoro-
3 -methyl benzam ide;
2,5-dichloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyI)methyl]thiophene-3-carboxamide;
2,6-dichloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)methy!]benzamide;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyC1-5hexyl)methyl]-2,4,6-
trimethylbenzamide;
2,4,6-trichloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)methyl] benzam ide;
(2E)-3-(2-chlorophenyl)-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyc!ohexyl)methyl]acrylamide;
5-bromo-N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-
methy l]th iophene-2 -carboxam ide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-2-(2,3,6-
trichlorophenyl)acetamide;
5-(4-chloro-2-nitrophenyI)-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yI]amino}cyclohexyl)methyl]-2-furamide;
5-chIoro-N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}cyclohexyl)-
methyI]thiophene-2-carboxamide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)methyl]-5-iodo-2-
furamide;
N-[(cis-4-{[4-(dimethylamino)quinoiin-2-yl]amino}cyclohexyl)methyl]-2-(2-
iodophenyl)acetamide;
(2E)-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-methyl]-3-
(3 -n itropheny 1 )acry lam ide;

878
2,2-bis(4-chlorophenyl)-N-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyl]acetamide;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)methyl]-5-
n i troth ioph ene-2 -carboxam ide;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)methyl]-3-methyl-
4-nitrobenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-3-
methoxy-4-nitrobenzamide;
N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-2-phenoxy-nicotinamide;
3,4-difIuoro-N-[cis-4-(4-methyI-quinolin-2-y!amino)-cyC1-5hexyl]-benzamide;
3,4-difluoro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyI]-benzamide;
2-phenoxy-N-[cis-4-(quinolin-2-yIamino)-cyclohexyl]-nicotinamide;
3-chloro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexy]]-benzamide;
N-[cis-4"(4-chloro-quinolin-2-ylamino)-cyclohexyl]-2-phenoxy-nicotinamide;
3 -methyl -N-[cis-4-(quinolin-2-y lam ino)-cyclohexyl]-benzamide;
3-methoxy-N-[cis-4-(quinolin-2-yIamino)-cyclohexyl]-benzamide;
3~chloro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
5-nitro-thiophene-3-carboxylic acid [cis-4-(quinolin-2-y!amino)-cyclohexyl]-
amide;
5-nitro-thiophene-3-carboxylic acid [cis-4-(4-methyl-quinolin-2-ylamino)-
cyc 1 ohexyl] -am ide;
3-chloro-4-fluoro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyI]-benzamide;
3,5-dimethoxy-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
3,4-dichIoro-N-[cis-4-(quinoIin-2-yIamino)-cyclohexyl]-benzamide;
benzo[2,3,l]oxadiazole-5-carboxylic acid [cis-4-(quinolin-2-yIamino)-cyclohexyl]-
amide;
3-methyl-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3-methoxy-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;

879
4-cyano-N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyclohexyl]-benzamide;
l-methyl-4-nitro-lH-pyrrole-2-carboxylic acid [cis-4-(quinolin-2-ylamino)-
cyclohexyl]-amide;
9H-xanthene-9-carboxylic acid [cis-4-(quinolin-2-ylamino)-cyclohexyl]-amide;
5-(4-chIoro-phenyl)-furan-2-carboxylic acid [cis-4-(quinolin-2-yIamino)-
cyclohexyl]-amide;
3-nitro-N-[cis-4-(quinolin-2-yIamino)-cyclohexyl]-benzamide;
4-fluoro-3-methyI-N-[cis-4-(quinoIin-2-yIamino)-cyclohexyl]-benzamide;
3-bromo-N-[cis-4-(quinoIin-2-ylamino)-cyclohexyl]-benzamide;
2-(2-bromo-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
3-cyano-N-[cis-4-(quinoIin-2-ylamino)-cyclohexyl]-benzamide;
N-[cis-4-(quinolin-2-ylamino)~cyclohexyl]-trifluoromethyl-benzamide;
N-[cis-4-(4-chloro-quinolin-2-yIamino)-cyclohexyl]-3,4-difluoro-benzamide;
3,4-dichloro-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3-chIoro-4-fluoro-N-[cis-4-(4-methy!-quinoIin-2-ylamino)-cyC1-5hexyl]-benzamide;
4-fluoro-3-methyl-N-[cis-4-(4-methyl-quinolin-2-ylaraino)-cyclohexyl]-
benzamide;
l~methyl-4-nitro-lH-pyrroIe-2-carboxyIic acid [cis-4-(4-methyl-quinolin-2-
y lam ino)-cyc lohexy 1] -amide;
9H-xanthene-9-carboxylic acid [cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexylj-
amide;
5-bromo-furan-2-carboxyIic acid [cis-4-(4-methyI-quinolin-2-ylamino)-
cyclohexyl]-amide;
N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyclohexyl]-2-/n-tolyloxy-acetamide;
N-[cis-4-(quinoIin-2-ylamino)-cyclohexyl]-2-m-tolyloxy-acetamide;
2,2-diphenyl-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide;
5-bromo-furan-2-carboxyIic acid [cis-4-(quinolin-2-ylamino)-cyclohexyl]-amide;

880
benzo[2,3,l]oxadiazole-5-carboxyIic acid [cis-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-amide;
3-bromo-N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyc]ohexyl]-benzamide;
3-cyano-N-[cis-4-(4-methy!-quinolin-2-ylamino)-cyclohexyl]-benzamide;
N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-3-trifluoromethyl-benzamide;
N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyl]-2,2-diphenyl-acetamide;
2-(4-fluoro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-fluoro-phenoxy)-N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyI]~
nicotinamide;
2-(3,4-difluoro-phenoxy)-N-[cis-4-(quinoIin-2-ylamino)-cyclohexyl]-
nicotinamide;
2-(3,4-difluoro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
nicotinamide;
N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-2-/7-toIyloxy-nicotinamide;
N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-2-73-tolyioxy-nicotinamide;
2-(4-chloro-phenoxy)-N-[cts-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-chloro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
nicotinamide;
2-(4-bromo-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyc I ohexyl]-nicotinamide;
2-(4-bromo-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
nicotinamide;
2-(4-methoxy-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyC1-5hexyl]-nicotinamide;
2-(4-methoxy-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
nicotinamide;
2-(3-chloro-4-fluoro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-
nicotinamide;
2-(3-chloro-4-fluoro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-nicotinamide;

881
N-[cis-4-(quinoIin-2-ylamino)-cyclohexyl]-2-m-tolyIoxy-nicotinamide;
N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-2-m-tolyloxy-nicotinamide;
2-(3-methoxy-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
acetamide;
2-(3-chloro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
acetamide;
2-(3-chloro-4-fluoro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-
cyclohexy]]-acetamide;
2-(3,4-dichloro-phenoxy)-N-[cis-4-(4-methyl-quinoiin-2-ylamino)-cyclohexyl]-
acetamide;
C-(methyl-phenyl-amino)-N-[cis-4-(4-methyI-quinolin-2-yIamino)-cyclohexyl]-
acetamide;
2-(3,4-dichloro-phenyIamino)-N-[cis-4-(4-methyl-quinolin-2-yIamino)-
cyclohexyl]-acetamide;
2-(3-methoxy-phenoxy)-N-[cis-4-(quino!in-2-ylamino)-cyclohexyl]-acetamide;
2-(3-chloro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide;
2-(3-chloro-4-fluoro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyC1-5hexyI]-
acetamide;
2-(3,4-dichIoro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide;
C-(methyl-phenyl-amino)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide;
2-(3,4-dichIoro-phenyJamino)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-
acetamide;
3-hydroxy-N-[cis-4-(quinolin-2-ylamino)-cyC1-5hexyl]-benzamide;
N-[cis-4-(quinoIin-2-yIamino)-cyclohexyl]-isophthalamic acid methyl ester;
N-[cis-4-(quinoIin-2-ylamino)-cyC1-5hexyI]-3-trifluoromethoxy-benzamide;
N-[cis-4-(4-methyI-quinoiin-2-ylamino)-cyclohexyl]-bis-trifluoromethyl-
benzamide;

882
N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyclohexy]]-3-trifluoromethoxy-
benzamide;
N-[cis-4-(4-amino-quinolin-2-ylamino)-cyC1-5hexyl]-3,4-difluoro-benzamide;
C-(ethyl-phenyl-amino)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyI]-acetamide;
C-(ethyl-phenyl-amino)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
acetamide;
3-hydroxy-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
2-amino-N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyclohexyl]-nicotinamide;
2,3-difIuoro-N-[cis-4-(4-raethyl-quinolin-2-ylamino)-cyC1-5hexy]]-benzamide;
2,4-difluoro-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-benzamide;
2,5-difIuoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
2,6-difluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3,5-difluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
C-[(4-chIoro-phenyI)-ethyl-amino]-N-[cis-4-(4-methyl-quinoIin-2-ylamino)-
cyclohexyl]-acetamide;
4-chloro-3-fluoro-N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyl]-benzamide;
4-fluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3-fluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-benzamide;
2-fluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
4-chloro-N-[cis-4-(4-methyI-quinolin-2-yIamino)-cyclohexyl]-benzamide;
N-[cis-4-(4-methyI-quinolin-2-yIamino)-cyclohexyI]-isophthalamic acid methyl
ester;
3r5-difluoro-N-[cis-4-(quinolin-2-ylamino)-cyC1-5hexyl]-benzamide;
4-chIoro-3-fluoro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
C-[(4-chloro-phenyI)-ethyl-amino]-N-[cis-4-(quinolin-2-ylamino)-cyC1-5hexyI]-
acetamide;
6-chloro-N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyclohexyl]-nicotinamide;

883
6-dimethylamino-N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyC1-5hexyl]-
nicotinamide;
3-hydroxymethyI-N-[cis-4-(4-methyI-quinoIin-2-ylamino)-cyclohexyl]-benzamide;
N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-isophthalamide;
3-chIoro-5-fIuoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3,4,5-trifluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
pyridine-2-carboxylic acid [cis-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyI]-
amide;
4-chIoro-pyridine-2-carboxylic acid [cis-4-{4-methyl-quinolin-2-ylamino)-
cyclohexyl]-amide;
5-bromo-N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyclohexyl]-nicotinamide;
N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyl]-6-trifluoromethyl-
nicotinamide;
3,4-difluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexylmethyl]-
benzamide;
N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexylmethyl]-2-phenoxy-
nicotinamide;
N-[cis-4-(4-dimethylamino-quinolin-2-ylamino)-cyclohexylmethy]]-3,4-difluoro-
benzamide;
3,4-difluoro-N-[cis-4-(quinolin-2-ylamino)-cyclohexylmethyl]-benzamide;
2-phenoxy-N-[cis-4-(quinolin-2-ylamino)-cyclohexyImethyl]-nicotinamide;
4-methyl-N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}benzamide;
2-(4-chlorophenoxy)-N-{cis-4-[(4-methylquinolin-2-
yl)amino]cyclohexyl}acetamide;
3,4,5-trimethoxy-N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}benzamide;
2-(3,4-difluorophenyI)-N-{cis-4-[(4-methylquinolin-2-
yl)amino] cyclohexyl} acetamide;

884
2-(2-bromo-4,5-dimethoxyphenyl)-N-{cis-4-[(4-methylquinoIin-2-
yl)amino]cyclohexyl}acetamide;
2,6-dimethoxy-N-{cis-4-[(4-methy!quinolin-2-yl)amino]cyC1-5hexyl}nicotinamide;
N-{cis-4-[(4-methy]quinolin-2-yl)amino]cyclohexyl}-4-
(trifluoromethoxy)benzamide;
5-chloro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide; and
5-fluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-nicotinamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
13. The compound according to claim 12 selected from the group consisting of:
3-bromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-
benzamide;
N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyc!ohexyl)-2,1,3-
benzoxadiazoIe-5 -carboxam ide;
3-chIoro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyc!ohexyl)-
benzamide;
4-chIoro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
benzamide;
4-chloro-N-(cis-4-{[4-(dtmethyIamino)quinolin-2-yl]amino}cyC1-5hexyl)-3-
nitrobenzamide;
3,4-dichloro-N-(cIs-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyC1-5hexyl)-3,4-
difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-
fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-3-nitrobenzamide;

885
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-2-
phenoxybutanamide;
N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-2-
phenoxypropan amide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-y]]amino}cyclohexyl)-3-
methylbenzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}cyclohexyI)-3-
methy I benzamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2,5-dimethyl-3-
furamide;
3-chIoro-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)-4-
fluorobenzamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-3,5-
dimethoxy benzamide;
N-(cis-4-{[4-(dtmethylamino)quinoIin-2-yl]amino}cyclohexyl)-4-fluoro-3-
methylbenzamide;
2-(4-chIorophenoxy)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)acetamide;
3-(2-chIorophenyl)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyI)-5-methy!isoxazole-4-carboxamide;
3-(2-chloro-6-fluorophenyI)-N-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)-5-methylisoxazo!e-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyc]ohexyl)-4-fluoro-3-
(trifluoromethyl)benzamide;
N-(cis-4~{[4-(dimethyIamino)quinoIin-2-yI]amino}cyclohexyl)-2-(4-
methoxyphenoxy)-5-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)qutnoiin-2-yl]amino}cyclohexyl)-5-nitro-2-
furamide;

886
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-
phenoxyacetamide;
2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}-
cyclohexyl)acetamide;
3-(2,6-dichlorophenyI)-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)-5-methylisoxazole-4-carboxamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-
phenoxynicotinamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-y]]amino}cyclohexyl)-2-(4-
methy lphenoxy)n icotinam ide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-2-(2-thienyl)-l,3-
thiazole-4-carboxamide;
N-(cis-4-{[4-(diraethylamino)quinolin-2-yl]amino}cyclohexyl)-2-(2,3,6-
trichlorophenyl)acetamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-5-iodo-2-furamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-5-nitrothiophene-
2-carboxamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-3-methyl-4-
nitrobenzamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyI)-3-methoxy-4-
nitrobenzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-2-
furamide;
4,5-dibromo-N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-cyclohexyl)-2-
furamide;
N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-2-(lH-indol-3-
yl)acetamide;

887
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-5-(3-nitrophenyl)-
2-furamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-5-nitrothiophene-
3-carboxamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)-l-methyl-4-nitro-
1 H-pyrrole-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-4-nitrobenzamide;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-3-fluoro-4-
(trifluoromethyl)benzamide;
3-bromo-N-[(cis-4-{[4-(dimethylaraino)quinolin-2-yl]amino}cyclohexyI)-
methyljbenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyC1-5hexyl)methyl]-2,l,3-
benzoxadi azo I e- 5 -carboxam ide;
3-chIoro-N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyI)-
methyl]benzamide;
4-chIoro-N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-
methy I]benzam ide;
4-chloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-methyI]-
3-nitrobenzamide;
3,4-dichloro-N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yI]amino}-
cyclohexyl)methyl]benzamide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)methyl]-3,4-
difluorobenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-4-
fluorobenzamide;
N-[(cis-4-{[4-(dimethy!amino)quinoIin-2-yI]araino}cyclohexyl)methyl]-3-
nitrobenzamide;

888
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)methyl]-2-
phenoxybutanamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyi)methyI]-2-
phenoxypropanam i de;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)methyl]-3-
methylbenzamide;
4-bromo-N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino} cyclohexyl)-methyl]-
3-methyIbenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-2,5-
dimethyI-3-furamide;
3-chloro-N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyC1-5hexyl)-methyl]-
4-fluorobenzamide;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)methyl]-3,5-
d imethoxybenzam ide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-4-fluoro-
3-methylbenzamide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}cyclohexyl)methyl]-2,4,6-
trimethylbenzamide;
2,4,6-trichloro-N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyc lohexy I)methy I] benzam ide;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-2-(2,3,6-
tri chloroph eny l)acetam ide;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)methyl]-5-iodo-2-
furamide;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)methyl]-5-
nitrothiophene-2-carboxamide;
N-[(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)methyI]-3-methyl-
4-nitrobenzamide;

889
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methy[]-3-
methoxy-4-nitrobenzamide;
N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-2-phenoxy-nicotinamide;
3,4-difluoro-N-[cis-4-(4-methyJ-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3,4-difluoro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
2-phenoxy-N-[cis-4-(quinoIin-2-ylamino)-cyclohexyI]-nicotinamide;
3-chloro-N-[cis-4-(4-methyl-quinoIin-2-yIamino)-cyclohexyl]-benzamide;
3-methyl-N-[cis-4-(quinoIin-2-yIamino)-cyC1-5hexyl]-benzamide;
3-methoxy-N-[cis-4-(quinolin-2-ylamino)-cyclohexyI]-benzamide;
3-chloro-N-[cts-4-(quinolin-2-ylamino)-cyC1-5hexyl]-benzamide;
5-nitro-thiophene-3-carboxylic acid [cis-4-(quinolin-2-ylamino)-cyclohexyl]-
amide;
5-nitro-thiophene-3-carboxyIic acid [cis-4-(4-methyl-quinolin-2-yIamino)-
cyclohexyl}-amide;
3-chloro-4-fluoro-N-[cis-4-(quinoIin-2-ylamino)-cyclohexyl]-benzamide;
3,5-dimethoxy-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
3,4-dichIoro-N-[cis-4-(quinolin-2-ylamino)-cyC1-5hexyl]-benzamide;
benzo[2,3,1]oxadiazole-5-carboxylic acid [cis-4-(quinoIin-2-ylamino)-cyclohexyl]-
amide;
3-methyl-N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyC1-5hexyl]-benzamide;
3-methoxy-N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyl]-benzamide;
4-cyano-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
l-methyI-4-nitro-IH-pyrrole-2-carboxylic acid [cis-4-(quinolin-2-ylamino)-
cyclohexylj-amide;
9H-xanthene-9-carboxyIic acid [cis-4-(quinolin-2-ylamino)-cyclohexyl]-amide;
3-nitro-N-[cis-4-(quinoIin-2-yIamino)-cyclohexyl]-benzamide;
4-fluoro-3-methyI-N-[cis-4-(quinolin-2-yIamino)-cyclohexyl]-benzamide;
3-bromo-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;

890
2-(2-bromo-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyI]-nicotinamide;
3-cyano-N-[cis-4-(quinolin-2-ylamino)-cyclohexylj-benzamide;
N-[cis-4-(quinolin-2-yIamino)-cyC1-5hexyl]-trifluoromethyl-benzamide;
N-[cis-4-(4-chloro-quinoIin-2-yiamino)-cyclohexyl]-3,4-difluoro-benzamide;
3,4-dichloro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-benzamide;
3-chIoro-4-fluoro-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-benzamide;
4-fluoro-3-methyl-N-[cis-4-(4-methyI-quinoIin-2-ylamino)-cyclohexyl]-
benzamide;
l-methyl-4-nitro-lH-pyrroIe-2-carboxylic acid [cis-4-(4-methyl-quinoIin-2-
ylamino)-cyclohexyl]-amide;
9H-xanthene-9-carboxylic acid [cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
amide;
5-bromo-furan-2-carboxylic acid [cis-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-amide;
N-[cis-4-(4-methyl-quinoiin-2-ylamino)-cyclohexyl]-2-m-tolyloxy-acetamide;
N-[cis-4-(quinolin-2-yIamino)-cyclohexyl]-2-/«-tolyloxy-acetamide;
2,2-diphenyl-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide;
5-bromo-furan-2-carboxylic acid [cis-4-(quinolin-2-ylamino)-cyclohexyl]-amide;
benzo[2,3,1 ]oxadiazoIe-5-carboxylic acid [cis-4-(4-methyl-quinoiin-2-ylamino)-
cyclohexyl]-amide;
3-bromo-N~[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3-cyano-N-[cis-4-(4-methyI-quinoiin-2-ylamino)-cyclohexyl]-benzamide;
N-[cis-4-(4-methyI-quinoIin-2-ylamino)-cyclohexyl]-3-trifluoromethyl-benzamide;
N-[cis-4-(4-methyI-qumolin-2-ylamino)-cyclohexyf]-2,2-diphenyl-acetamide;
2-(4-fIuoro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-fluoro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
nicotinamide;

891
2-(3,4-difluoro-phenoxy)-N-[cis-4-(quinoIin-2~ylamino)-cyclohexyl]-
nicotinamide;
2-(3,4-difluoro-phenoxy)-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-
nicotinamide;
N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-2-/7-tolyloxy-nicotinamide;
N-[cis-4-(4-methyI-quinoIin-2-ylamino)-cyclohexyl]-2-p-tolyloxy-nicotinamide;
2-(4-ch!oro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-chloro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyclohexyl]-
nicotinamide;
2-(4-bromo-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-bromo-phenoxy)-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyI]-
nicotinamide;
2-(4-methoxy-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
2-(4-methoxy-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-
nicotinamide;
2-(3-chloro-4-fluoro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-yIamino)-
cyclohexylj-nicotinamide;
N-[cis-4-(quinolin-2-ylamino)-cyC1-5hexyl]-2-w-toIyloxy-nicotinamide;
N-[cis-4-(4-methyl-quinoIin-2-ylamino)-cyclohexyI]-2-m-tolyloxy-nicotinamide;
2-(3-methoxy-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
acetamide;
2-(3-chloro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
acetamide;
2-(3-chtoro-4-fluoro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-
cyclohexyl]-acetamide;
2-(3,4-dichloro-phenoxy)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
acetamide;

892
C-(methyl-phenyl-amino)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-
acetamide;
2-(3-methoxy-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-acetamide;
2-{3-chloro-phenoxy)-N-[cis-4-(quinolin-2-yIamino)-cyclohexyl]-acetamide;
2-(3-chloro-4-fluoro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-
acetamide;
2-(3,4-dichloro-phenoxy)-N-[cis-4-(quinolin-2-ylamino)-cyclohexyI]-acetamide;
C-(methyl-phenyl-amino)-N-[cis-4-(quinoIin-2-ylamino)-cyC1-5hexyl]-acetamide;
N-[cis-4-(4-methyl-quinolin-2-yIamino)-cyclohexyi]-3-trifluoromethoxy-
benzamide;
N-[cis-4-(4-amino-quinoIin-2-ylamino)-cyclohexyl]-3,4-difluoro-benzamide;
C-(ethyl-phenyl-amino)-N-[cis-4-(quinoIin-2-yIamino)-cyclohexyl]-acetamide;
C-(ethyl-phenyl-amino)-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-
acetamide;
3-hydroxy-N-[cis-4-(4-methyI-quinoIin-2-ylamino)-cyclohexyl]-benzamide;
2,4-difluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-benzamide;
3,5-difluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-benzamide;
C-[(4-chloro-phenyI)-ethyl-amino]-N-[cis-4-(4-methyl-quinolin-2-yIamino)-
cyc tohexy 1] -ac etamide;
4-chloro-3-fluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-benzamide;
4-fluoro-N-[cis-4-(4-methyI-quinolin-2-ylamino)-cyclohexyl]-benzamide;
3-fluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyI]-benzamide;
4-chloro-N-[cis-4-(4-methyi-quinoIin-2-ylamino)-cyclohexyl]-benzamide;
N-[cis-4-(4-methyI-quinoIin-2-ylamino)-cyclohexyl]-isophthalamic acid methyl
ester;
3,5-difluoro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;
4-chloro-3-fluoro-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-benzamide;

893
C-[(4-chIoro-phenyl)-ethy]-amino]-N-[cis-4-(quinolin-2-ylamino)-cyclohexyl]-
acetamide;
6-chIoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotmamide;
3-chloro-5-fluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyC1-5hexyl]-ben2amide;
3,4,5-trifluoro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-benzamide;
5-bromo-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide;
4-methyI-N-{cis-4-[(4-methylquinoIin-2-yl)amino]cyclohexyl}benzamide;
2-(4-chlorophenoxy)-N-{cis-4-[(4-methylquinolin-2-yl)amino]cyC1-5hexyl}-
acetamide;
3,4,5-trimethoxy-N-{cis-4-[(4-methylquinolin-2-yl)amino]cyC1-5hexyl}benzamide;
2-(3,4-difluorophenyl)-N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}-
acetamide;
2-(2-bromo-4,5-dimethoxyphenyl)-N-{cis-4-[(4-methylquinolin-2-yl)araino]-
cyclohexyl} acetamide;
2,6-dimethoxy-N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}nicotinamide;
N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}-4-(trifluoromethoxy)-
benzamide;
5-chloro-N-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-nicotinamide; and
5-fluoro~N-[cis-4-(4-methyi-quinolin-2-y]amino)-cyclohexyl]-nicotinamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
14. The compound according to claim 3 wherein Rj is selected from the group consisting of:
Ci-i6 alky I, and
C1-16 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:

894
••halogen,
••C1-5 alkyl,
••C1-5 alkyl substituted by halogen,
••C1-5 alkoxy, and
••Cj-s alkoxy substituted by halogen,
L is Formula (XV);
Y is -C(O)NR5-;
wherein carbocyclic aryl is phenyl; and
halogen is fluoro, chloro, or bromo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
15. The compound according to claim 14 wherein R, is selected from the group consisting of:
Ci_i6 alkyl, and
C1-16 alkyl substituted by substituent(s) independently selected from the group
consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
wherein carbocyclic aryl is phenyl; and
halogen is fluoro, chloro, or bromo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
16. The compound according to claim 14 or 15 wherein R2 is methyl; p is 0; R3 and R4 are both
hydrogen; A and B are both single bonds; and R5 is hydrogen;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.

895
17. The compound according to claim 1 selected from the group consisting of:
cis-N-[( 1R)-1 -(4-bromophenyI)ethy l]-4-[(4-methylquinolin-2-
yl)amino]cyclohexanecarboxamide;
cis-N-{(lS)-l-[3,5-bis(trifluoromethyl)phenyl]ethyl}-4-[(4-methylquinolm-2-
yl)amino]cyclohexanecarboxamide;
cis-N-[(lR)-]-(2-fluorophenyl)ethyI]-4-[(4-methylquinolin-2-
yl)amino]cyclohexanecarboxamide;
cis-N-[(lS)-l-(2-fluorophenyl)ethyl]-4-[(4-methylquinolin-2-
yl)amino]cyclohexanecarboxamide;
cis-4-[(4-methylquinolin-2-yl)ammo]-N-{(lS)-l-[2-
(tri fluoromethy l)pheny 1 ] ethyl} eye lohexanecarboxam ide;
cis-4-[(4-methylquinolin-2-yl)amino]-N-{(lS)-l-[3-
(tri fluoromethy l)phenyl] ethyl} eye lohexanecarboxam ide;
cis-N-[( 1R)-1 -(4-chlorophenyl)ethyi]-4-[(4-methylquinolin-2-
yl)amino]cyclohexanecarboxamide; and
cis-N-[(lS)-l-(4-chlorophenyI)ethyl]-4-[(4-methylquinolin-2-
yl)amino]cyclohexanecarboxamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
18. The compound according to claim 1 selected from the group consisting of:
cis-N-[( 1R)-1 -(4-bromophenyl)ethyl]-4-[(4-methylquinolin-2-
yl)amino]cyclohexanecarboxamide;
cis-N-[( 1S)-1 -(2-fluorophenyl)ethyl]-4-[(4-methylquinolin-2-
yl)amino]cyclohexanecarboxamide;
cis-4-[(4-methylquinolin-2-yl)amino]-N-{(lS)-l-[2-
(trifluoromethyl)phenyl]ethyl}cyC1-5hexanecarboxamide; and

896
cis~4-[(4-methylquinoIin-2-yl)amino]-N'{(lS)-l-[3-
(trifluoromethyl)phenyl]ethyl}cyclohexanecarboxamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
19. The compound according to claim 3 wherein Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
■C1-5 alkoxycarbonyl,
•Cj.s alkylthio,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
••C2-5 alkenyl,
(ii) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by carbocyclic aryl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•cyano,
•nitro,
•C1-5 alkyt,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxycarbonyl,
•C1-5 alkoxy,

897
•C1-5 alkoxy substituted by carbocyclic aryi,
•C3-6 cycloalkoxy,
•carbocyciic aryloxy,
•Cj_5 alkylthio, and
•carbocyclic aryl,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•C,-5 alkyl,
•C1-5 alkyl substituted by halogen, and
•carbocyclic aryl;
L is Formula (VII);
Y is -C(O)NR5-;
wherein carbocyclic aryl is phenyl or naphthyi;
heterocyclyl is 2,3-dihydro-benzo[l,4]dioxinyl, 3,4-dihydro-2#-
benzo[b][l,4]dioxepinyl, benzo[l,3]dioxolyl, furyl, or isoxazolyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
20. The compound according to claim 19 wherein R2 is hydrogen, methyl, methylamino, or
di methyl am ino; p is 0; R3 and R4 are hydrogen; A is a single bond; B is a single bond or
-CH2-; R5 is hydrogen; or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
21. The compound according to claim 20 wherein Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkoxycarbonyl,

898
•carbocyclic aryl, and
•carbocyclic aryl substituted by halogen,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen, and
•C1-5 alkoxy,
(iii) heterocyclyl,
heterocyclyl substituted by C1-5 alkyl, and
heterocyciyl substituted by carbocyclic aryl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is isoxazolyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
22. The compound according to claim 1 selected from the group consisting of:
N-(2-chIorophenyI)-N'-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}-
cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-(2-ethyI-6-
methylphenyl)urea;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-mesitylurea;
N-(cis-4-{[4-(dimethyIamino)quinoIin-2-yl]amino}cyclohexyl)-N'-(2,4,6-
trichlorophenyl)urea;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-(2,4,6-
tribromophenyl)urea;

899
N-(2,4-dibromo-6-fluorophenyl)-N'-(cis-4-{[4-(dimethylamino)quinoIin-2-
yljamino} cyclohexyl)urea;
N-(2,6-diethylpheny!)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-yI]amino}-
cyclohexyl)urea;
N-(2-chlorobenzyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-N'-(2-ethyl-6-
isopropylphenyl)urea;
N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-N'-(2-isopropyI-6-
methylphenyl)urea;
N-(2-tert-butyI-6-methyIphenyl)-N'-(cis-4~{[4-(dimethyIamino)quinoIin-2-
yl]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)quinoHn-2-yl]amino}cyclohexyl)-N'-
(diphenylmethyl)urea;
N-(4-bromo-2,6-dimethylphenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yljamino} cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)quinoIin-2-yl]amino}cyclohexyl)-N'-t3-methyl-5-
phenylisoxazol-4-yl)urea;
N-(cis-4- {[4-(dimethylamino)quinolin-2-yl]amino} cyclohexyl)-N'-1 -naphthylurea;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyI)-N'-[l-(l-
naphthyl)ethy]]urea;
methyl N-{[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyI)-
amino]carbonyl}phenylalaninate;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-(3,4,5-
trimethoxyphenyl)urea;
N-(5-chloro-2,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethyIamino)quinolin-2-
yl]amino}cyclohexyl)urea;

900
N-(4-bromo-2-methy]phenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)urea;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-N'-(2-
ethyl-6-methylphenyl)urea;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)methyI]-N'-
mesitylurea;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-N'-(2,4,6-
trichiorophenyl)urea;
N-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)methyl]-N'-(2,4,6-
tribromophenyl)urea;
N-(2,4-dibromo-6-fluorophenyl)-N'-[(cis-4-{[4~(dimethylamino)quinoIin-2-
yl]amino}cyclohexyl)methyi]urea;
N-(2,6-diethyIphenyl)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}-
cyclohexyl)methyl]urea;
N-[2-chloro-6-(trifIuoromethyl)phenyI]-N'-[(cis-4-{[4-(dimethylamino)-quinolin-
2-yl]amino}cyclohexyI)methyl]urea;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyI]-N'-(2-
ethyI-6-isopropylphenyl)urea;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-N'-(2-
i sopropy 1-6-methy lpheny I)urea;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyl]-N'-(2-
methy 1-3 -n itrophenyl)urea;
N-(2-tert-butyI-6-methylphenyi)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyl]urea;
N-(2-tert-butylphenyI)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]-
amino}cyclohexyl)methyl]urea;
N-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)methyI]-N'-
(diphenylmethyl)urea;

901
N-(4-bromo-2,6-dimethylphenyl)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)methyl]urea;
N-(2,3-dichlorophenyI)-N'-[(cis-4-{[4-(dimethylamino)quinolin-2-yl]-
amino} cyclohexyl)methyl]urea;
N-(2,6-diisopropyIphenyl)-N'-[(cis-4-{[4-(dimethyIamino)quinolin-2-yl]-
amino} cyclohexyl)methyl]urea;
I-(2,3-dichloro-phenyl)-3-[cis-4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-urea;
and
l-(2,3-dichIoro-phenyl)-3-[cis-4-(4-methyl-quinolin-2-yIamino)-
cyclohexylmethyl]-urea;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
23. The compound according to claim 3 wherein R] is selected from the group consisting of:
(i) Ci-g alkyl, and
Ct-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
••C1-5 alkoxy,
(ii) carbocyclyl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•cyano,
•nitro,

902
•C1-5 alkyl,
•C1-5 alky! substituted by halogen,
•C1-5 alkoxy carbonyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by halogen,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino, and
•carbocyclic aryl,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkyl,
•Ci_s alkoxy carbonyl, and
•carbocyclic aryl;
L is Formula (VII);
Y is -C(S)NR5-;
wherein carbocyclic aryl is phenyl or naphthyl;
carbocyclyl is bicyclo[2.2.1]heptyl;
heterocyclyl is 2,3-dihydro-benzo[l,4]dioxinyl, benzo[l,3]dioxolyl,
isoxazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
24. The compound according to claim 23 wherein R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-; R5 is hydrogen;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
25. The compound according to claim 24 wherein Ri is selected from the group consisting of:

903
(i) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•C 1.5 alky 1,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy,
•mono-C1-5 alkylamino, and
•di-C1-5 alkylamino,
(ii) heterocyclyl, and
heterocyclyl substituted by C1-5 alkyl, and
heterocyclyl substituted by C1-5 alkoxy carbonyl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
26. The compound according to claim 1 selected from the group consisting of:
N-(2,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]-
amino}cyclohexyl)thiourea;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexyl)-N'-(3,4,5-
trimethoxyphenyl)thiourea;
N-[4-(dimethylamino)-l-naphthyl]-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
y l]amino} cyclohexyl)thiourea;
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-(2,4,6-
tribromophenyl)thiourea;
N-(cis-4-{[4-(dimethyIamino)quinolin-2-yl]amino}cyclohexy])-N'-(2,4,6-
trichlorophenyl)thiourea;

904
N-(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-N'-
mesitylthiourea;
N-(2,6-diethylphenyl)-N'-(cis-4-{[4-(dimethylamino)quinoIin-2-yI]amino}-
cyclohexyl)thiourea;
N-(4-bromo-2,6-dimethylphenyt)-N'-(cis-4-{[4-(dimethylamino)quinoIin-2-
yljamino} cyclohexyl)thiourea;
N-(4-bromo-2-methyIphenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)thiourea;
N-[4-bromo-2-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethylamino)-quinolin-2-
yl]amino}cyclohexyl)thiourea;
N-(5-chloro-2,4-dimethoxyphenyI)-N'-(cis-4-{[4-(dimethylamino)quinoIin-2-
yt]amino}cyclohexyl)thiourea;
N-(2,4-dibromo-6-fluorophenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)thiourea;
N-(2,4-dichloro-6-methyIphenyl)-N'-(cis-4-{[4-(dimethylamino)quinolin-2-
yl]amino}cyclohexyl)thiourea;and
methyl 3-({[(cis-4-{[4-(dimethylamino)quinolin-2-yl]amino}cyclohexyl)-
amino]carbonothioyl}amino)-4-methyIthiophene-2-carboxylate;
or a pharmaceutical ly acceptable salt, hydrate, or solvate thereof.
27. The compound according to claim 3 wherein R] is selected from the group consisting of:
(i) C].a alkyl, and
Ci_8 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclyl,

905
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
••C1-5 alkoxy,
(ii) C2-5 alkenyl,
(iii) carbocycly!,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen, and
•C1-5 alkoxy;
L is Formula (VII);
Y is -C(O)O-;
wherein carbocyclic aryl is phenyl or naphthyl;
carbocyclyl is 9//-fluorenyl or menthyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
28. The compound according to claim 27 wherein R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
29. The compound according to claim 2 wherein Q is Formula (III);
R.! is selected from the group consisting of:

906
(i) Ci-8 alkyl, and
Ci-8 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•C1-5 alkylcarbonyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by nitro,
•heterocyclyloxy,
•heterocyclyloxy substituted by C1-5 alkyl,
•C1-5 alkoxycarbonyl,
•mono-C1-5 alky lam inocarbonyl,
•dt-Ci-s alkylaminocarbonyl,
•mono-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•mono-C1-5 alkylamino substituted by carbocyclic aryl,
•di-C1-5 alkylamino,
•di-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino substituted by carbocyclic aryl,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by C1-5 alkyl,
•di-carbocyclic arylamino,
•di-carbocyclic arylamino substituted by C1-5 alkyl,
•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted C1-5 alkyl,

907
•C[.s alkylthio,
•C1-5 alkylthio substituted by substituent(s) independently selected from
the group consisting of:
••carbocyclic aryl,
••carbocyclic aryl substituted by halogen, and
"carbocyclic ary] substituted by C1-5 alkoxy,
•carbocyclic arylthio,
•heterocyclylthio,
•heterocyclylthio substituted by C1-5 alkyl,
•C3^ cycloalkyl,
•C3-6 cycloalkenyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
-C1-5 alkyl,
••C1-5 alkoxy,
••C2-5 alkenyl., and
"C?-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••nitro,

908
-C1-5 alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••oxo,
•••carbocyclic aryl, and
•••heterocyclyi,
"C2-5 alkenyl,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by halogen,
"C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryloxy,
••mono-carbocyclic arylaminocarbonyl,
—mono-carbocyclic arylaminocarbonyl substituted by halogen,
••di-carbocyclic arylaminocarbonyl,
••di-carbocyclic arylaminocarbonyl substituted by halogen,
••carbocyclic aryl, and
••heterocyclyl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5 alkyl,
••C1-5 alkoxy,
••Ct-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryl, and
••carbocyclic aryl substituted by halogen,
(ii) C2-7 alkenyl, and
C2-7 alkenyl substituted by substituent(s) independently selected from the
group consisting of:

909
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
••C1-5 alkoxy,
(iii) C2-5 alkynyl,
(iv) C3.12 cycloalkyl, and
C3.12 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:
•C,-5 alkyl,
•Cj_5 alkyl substituted by oxo,
•C1-5 alkyl substituted by carbocyclic aryl, and
•carbocyclic aryt,
(v) carbocyclyl,
(vi) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
•Cwo alkyl,
•C1-5O alkyi substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••oxo,
••carbocyclic aryloxy,

910
••carbocyclic aryl, and
••carbocyclic aryl substituted by C1-5 alkyl,
•C1.7 alkoxy,
•Ct-7 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
'•carbocyclic aryl, and
••halogenated carbocyclic aryl,
•C2-5 alkenyloxy,
•C3-6 cycloalkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by nitro,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•carboxy,
•C1-5 alkoxy carbonyl,
•mono-C1-5 alkyl am inocarbonyl,
•di-Cj_5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•amino,
•mono-C1-5 alkylamino,
•di-Cj.5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino substituted by cyano,
•C2-5 alkynylcarbonylamino,
•C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,
•C1-5 alkoxycarbonylamino,
•(carbocyclic aryl)NHC(O)NH,

911
•(carbocyclic aryl)NHC(O)NH substituted by C1-5 alkoxy,
•(carbocyclic aryl)NHC(O)NH substituted by haloganated Ct_5 alkoxy,
•carbocyclic aryl azo,
•carbocyclic aryl azo substituted by mono-C1-5 alkylamino,
•carbocyclic aryl azo substituted by di-C1-5 alkylamino,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by halogen,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by nitro,
•carbocyclic arylthio substituted by cyano,
•aminosulfonyl,
•mono-C1-5 alkylaminosulfonyl.,
•di-C1-5 alkylaminosulfonyl,
•heterocyclylsulfonyl,
•C3-6 cycloalkyl,
•C3-6 cycloalkyl substituted by C1-5 alkyl,
•carbocyclic aryl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
»C1-5 alkyl,
••carbocyclic aryl, and
••halogenated carbocyclic aryl,
(vii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,

912
-C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••hydroxy,
"C1-5 alkylthio,
••C1-5 alkylthio substituted by carbocyclic aryl,
••Ci,5 alkylthio substituted by halogenated carbocyclic aryl,
••carbocyclic aryl,
••carbocyclic aryl substituted by halogen, and
••heterocyclyl,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkyl,
•C1-5 alkylthio,
•C2.5 alkenylthio,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by C1-5 alkoxycarbonyl,
•C1-5 alkylsulfonyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by Cj_5 alkyl,
•C1-5 alkoxy carbonyl,
•C1-5 alkoxy carbonyl substituted by carbocyclic aryl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,

913
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
•heterocyclyl;
wherein carbocyclic aryl is phenyl, naphthyl, or anthranyl;
carbocyclyl is 1,2,3,4-tetrahydronaphthyl, 1-oxo-indanyl, 9-fluorenyI, 9H-
fluorenyl, 9-oxo-9#-fluorenyl, adamantly, bicyclo[2.2.1]heptenyl.,
bicyclo[2.2.1]heptyl, indanyl, indenyl, ormenthyl;
heterocyclyl is 1,2,3-triazolyl, li/-indolyl, l//-pyrrolyl, 2,3-dihydro-l-
oxo-isoindolyl, 2,3-dihydro-benzo[l,4]dioxinyl, 2,4-dihydro-3-oxo-pyrazolyl, 2H-
benzopyranyl, 2-oxo-benzopyranyi, 3,4-dihydro-2//-benzo[b}[l,4]dioxepinyl,
4,5,6,7-tetrahydro-benzo[b]thienyI, 4//-benzo[l,3]dioxinyl, 4-oxo-l,5,6,7-
tetrahydro-indolyl, 4-oxo-benzopyranyl, 9//-carbazolyl, 9//-xanthenyl, azetidinyl,
benzo[l,3]dioxolyl, benzo[2,l,3]oxadiazolyl, benzo[l,2,5]oxadiazolyl,
benzo[2,l,3]thiadiazolyl, benzo[b]thienyl, benzofuryl, benzothiazolyl, furyl,
imidazo[2,l-b]thiazolyl, isoxazolyl, morpholino, morpholinyl, oxazolyl,
phenanthro[9,I0-d]oxazolyl, piperidyl, pyrazoiyl, pyridyl, pyrimidyl, quinolyl,
quinoxalyl, tetrahydrofuryl, thiazolyl, orthienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
30. The compound according to claim 29 wherein Rj is selected from the group consisting of:
(i) Ci-7 alkyl, and
Ci-7 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclic aryloxy,
•mono-C1-5 alkylamino,

914
•mono-C]-5 alkylamino substituted by substituent(s) independently selected
from the group consisting of:
"cyano, and
••carbocyclic aryl,
•di-C1-5 alkylamino,
•di-C]o alkylamino substituted by substituent(s) independently selected
from the group consisting of:
••cyano, and
••carbocyclic aryl,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by C1-5 alkyl,
•di-carbocyclic arylamino substituted by C1-5 alkyl,
•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted by Ci,5 alkyl,
•carbocyclic aryl,
"carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,
••C1-5 alkyl,
"C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••oxo, and
•••carbocyclic aryl,
••C1-5 alkoxy,
•heterocyclyl, and
•heterocydyl substituted by carbocyclic aryl,

915
(ii) C7-7 aikenyl, and
C2-7 aikenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by C1-5 alkoxy,
(iii) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:
•C1-5 alkyl, and
•C1-5 alkyl substituted by carbocyclic aryl,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•cyano,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••carbocyclic aryl,
••carbocyclic aryl substituted by halogen,
•C2-5 alkenyloxy,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,

916
•di-C1-5 alkylamino substituted by cyano,
•C1-5 alkylthio, and
•C1-5 alkylthio substituted by halogen,
(v) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•d.5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••hydroxy, and
••carbocyclic aryl,
*C1-5 alkoxy,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by C1-5 alkoxycarbonyl,
•C1-5 alkoxycarbonyl,
•carbocyclic aryl,
"carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
"C1-5 alkyl substituted by halogen;
L is Formula (VII);
Y is a single bond or -CH2-;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is 1/f-indolyl, l//-pyrrolyl, 2,3-dihydn>benzo[l,4]dioxinyl,
4-oxo-benzopyranyl, 9//-carbazolyl, azetidinyl, benzo[l,3]dioxolyl,
benzo[b]thienyl, furyl, imidazo[2,l-b]thiazolyl, pyrazolyl, pyridyl, or thienyl; and

917
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
31. The compound according to claim 30 wherein R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
32. The compound according to claim 31 wherein R] is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•mono-C1-5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino,
•di-C1-5 alkylamino substituted by cyano,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by C1-5 alkyl,
•di-carbocyclic arylamino substituted by C1-5 alkyl,
•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted by C1-5 alkyl,
•carbocyclic aryl, and
•carbocyclic aryl substituted by C1-5 alkoxy,
(ii) C2_5 alkenyl, and
C2-5 alkenyl substituted by carbocyclic aryl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:

918
•halogen,
•hydroxy,
•Chalky],
•C1-5 alkoxy,
•C1-5 alkoxy substituted by halogen,
•mono-C1-5 alkylamino, and
•di-C1-5 alkylamino,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•CLS alkyl,
•C1-5 alkyl substituted by carbocyclic aryl,
•C1-5 alkoxy,
•C1-5 alkoxycarbonyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
"C1-5 alkyl, and
"C1-5 alkyl substituted by halogen;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is l//-indolyl, 4-oxo-benzopyranyl, azetidinyl,
benzo[l,3]dioxolylJ orpyrazolyl; and
halogen is ftuoro, ch!oro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
33. The compound according to claim 32 wherein Ri is selected from the group consisting of:

919
(i) C1-5 alkyl, and
C1-5 alky! substituted by substituent(s) independently selected from the
group consisting of:
•mono-C1-5 alkylamino,
■mono-C1-5 alkylamino substituted by cyano,
•di-Cj.5 alkylamino,
•di-C1-5 alkylamino substituted by cyano,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,
•carbocyclic arylsulfonylamino,
•carbocyclic arylsulfonylamino substituted by C1-5 alkyl, and
"carbocyclic aryl,
(ii) C2-5 alkenyl, and
C2-5 alkenyl substituted by carbocyclic aryl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•C1-5 alkoxy, and
•C1-5 alkoxy substituted by halogen,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkyl,
•C1-5 alkyl substituted by carbocyclic aryl,
•C,_5 alkoxy,

920
•C1-5 alkoxycarbonyl,
•carbocyclic aryl, and
•carbocyclic aryl substituted by halogen;
wherein carbocyclic aryl is phenyl;
heterocyclyl is \H-indo\y\, azetidinyl, orpyrazolyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
34. The compound according to claim 1 selected from the group consisting of:
N2-{cis-4-[(2,6-dimethoxybenzyl)amino]cyC1-5hexyl}-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-{cis-4-[(2-ethoxybenzyl)amino]cyclohexyl}-N4,N4-dimethyI-5,6,7,8-
tetrahydroquinazol ine-2,4-diamine;
N2-{cis-4-[(lH-indol-3-ylmethyI)amino]cyclohexyl}-N4,N4-dimethyl-5,6,7,8-
tetrahydroqui nazo 1 ine-2,4-diamine;
N2-{cis-4-[(2,5-dimethoxybenzyl)amino]cyclohexyl}-N4,N4-dimethyI-5,6,7,8-
tetrahydroquinazoIine-2,4-diamine;
N2-(cis-4- {[(4-methoxy-1 -naphthyl)methyl]amino} cyclohexyl)-N4,N4-dimethyl-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(5-methoxy-lH-indol-3-yI)methyl]amino}cyclohexyl)-N4TN4-dimethyI-
5,6,1,8-tetrahydroquinazo 1 ine-2,4-d i am ine;
4-bromo-2-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)amino]methyI}-6-methoxyphenol;
N2-(cis-4- {[(5-bromo-1 H-indol-3-yI)methy l]amino} eye lohexyl)-N4,N4-di methyl-
5,6,7,8-tetrahydroquinazo 1 ine-2,4-d iamine;
4-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyl)amino]methyl}-2,6-dimethoxyphenol;

921
N2-{cis-4-[(3-ethoxy-4-methoxybenzyl)amino]cyclohexyl}-N4,N4-dimethyl-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethyl-N2-{cis-4-[({3-[4-(trifluoromethyl)phenyI]-lH-pyrazol-4-
yl}methyl)amino]cyclohexyl}-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethyl-N2-{cis-4-[(3,4,5-trimethoxybenzyl)amino]cyC1-5hexyl}-5,6,7,8-
tetrahy droqu inazol ine-2,4-d i am i ne;
N4,N4-dimethyl-N2-{cis-4-[(pentamethylbenzyl)amino]cyC1-5hexyl}-5,6!7,8-
tetrahydroquinazoline-2,4-diamine;
N2-{cis-4-[(3,5-dimethoxybenzyl)amino]cyclohexyl}-N45N4-dimethyl-5,6,7,8-
tetrahy droqu inazol ine-2,4-d i am ine;
4-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)amino]methyl}-2-iodo-6-methoxyphenol;
4- {[(cis-4- {[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino} -
cyclohexyl)amino]methyl} -2,6-dimethylphenol;
3-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)amino]methyl}-6,8-dimethyl-4H-chromen-4-one;
ethyl 4,6-dichloro-3-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)amino]methyl}-lH-indole-2-carboxylate;
N2-[cis-4-({[3-(4-fluorophenyI)-lH-pyrazol-4-yl]methyl}amino)cyclohexyl]-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethy!-N2-[4-(pentamethylphenylmethyl-amino)-cyclohexyI]-5,6,7,8-
tetrahydro-quinazoline-2,4-diamine;
3-[{2-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)amino]ethyl}(3-methylphenyl)amino]propanenitrile;
3-[{2-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)amino]ethyl}(phenyl)amino]propanenitrile;
N-{(lS)-l-benzyl-2-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)amino]ethyl}-4-methylbenzenesulfonamide;

922
N2-(cis-4-{[2-(3,5-dimethoxyphenyl)ethyl]amino}cyclohexyI)-N4,N4-dimethyl-
5,6,7,8-tetrahydroqu i nazol ine-2,4-d iam i ne;
N2-[cis-4-({[l-(diphenylmethyl)azetidin-3-yl]methyl}amino)cyclohexyl]-N4,N4-
dimethyI-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(2,6-dimethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-dimethy]-
5,6,7,8-tetrahydroquinazoIine-2,4-diamine;
N2-(cis-4-{[(2-ethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-dimethyl-5,6,7,8-
tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(lH-indol-3-ylmethyl)amino]methyl}cyC1-5hexyl)-N4,N4-dimethyI-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(2,5-dimethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-dimethyI'
5,6,7,8-tetrahydroqu inazoline-2,4-diamine;
N2-[cis-4-({[t4-methoxy-l-naphthyl)methyl]amino}methyI)cyclohexyl]-N4,N4'
dimethyI-536,7,8-tetrahydroquinazoline-2,4-diamine;
N2-[cis-4-({[(5-methoxy-lH-indol-3-yI)methyl]amino}methyl)cyclohexyl]-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
4-bromo-2-({[(cts-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]amino}methyl)-6-methoxyphenol;
N2-[cis-4-({[(5-bromo-IH-indoI-3-yI)methylJamino}methyl)cyclohexyI]-N4,N4-
d i methyl -5,6,7,8-tetrahydroquinazo I ine-2,4-d i am ine;
N2-(cis-4-{[(3-ethoxy-4-methoxybenzyI)amino]methyl}cyC1-5hexyl)-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[({3-[4-(trifluoromethyl)phenyl]-lH-pyrazoI-4-
yI}methyI)amino]methyI}cyC1-5hexyl)-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(3,4,5-trimethoxybenzyl)amino]-methyl}cyclohexyI)-
5,6,7,8-tetrahydroquinazoIine-2;4-diamine;
N2-(cis-4-{[(3,5-dimethoxyben2yI)amino]methyl}cyclohexyl)-N'i!N4-dimethyl-
5,6,7,8-tetrahydroquinazoHne-2,4-diamine;

923
4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]amino}methyI)-2-iodo-6-methoxyphenol;
4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyI]amino}methyl)-2,6-dimethylphenol;
3-chloro-4-({[(cts-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino} cyclohexyl)methyl]amino} methy l)phenol;
N"-[cis-4-({[4-(diethylamino)benzyl]amino}methyl)cyclohexyl]-N4,N4-dimethyl-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(3,3-diphenylprop-2-en-l-y])amino]methyl}cyclohexyl)-N4,N4-
dimethyI-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
4-( {[(cis-4- {[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]amino}methyl)-2-ethoxyphenoi;
N2-{cis-4-[({[4-(dimethylamino)-l-naphthyl]methyl}amino)methyl]-cyclohexyI}-
N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,6-trimethoxybenzyl)amino]methyl}-cyclohexyl)-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
2-bromo-4-chloro-6-({[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino} cyclohexyl)methyl]amino} methy l)phenol;
N2-(cis-4-{[(2,5-diethoxybenzyI)amino]methyl}cyclohexyI)-N4,N4-dimethyl-
5,6,7,8-tetrahydroquinazoIine-2,4-diamine;
N2-(cis-4-{[(2,4-diethoxybenzyI)amino]methyl}cyclohexyl)-N45N4-dimethyl-
5,6,7,8-tetrahydroqu inazol ine-2,4-diam i ne;
N"-(cis-4-{[(3,5-dibromo-2-methoxybenzyl)amino]methyl}cyC1-5hexyl)-N4,N4-
dimethyI-5,6,7,8-tetrahydroquinazoIine-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-triethoxybenzyl)amino]methyl}-cyclohexyl)-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-trimethoxybenzyl)amino]methyl}-cyclohexyl)-
5,6,7,8-tetrahydroqumazoline-2?4-diamine;

924
N2-[cis-4-({[(7-methoxy-l,3-benzodioxol-5-yl)methyl]amino}methyl)-
cyclohexyl]-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
4-({[(cis-4-{[4-(dimethylarnino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]amino}methyI)-2-methylphenol;
N2-(cis-4-{[(4-methoxy-2,5-dimethyIbenzyI)amino]methyl}cyclohexyl)-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]amino}methyl)-2-fluoro-6-methoxyphenol;
N4,N4-dimethyl-N2-[cis-4-( {[(1 -phenyl-5-propyl-1 H-pyrazol-4-
yl)methyl]amino}methyl)cyclohexyI]-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N2-{cis-4-[( {[ 1 -(4-chlorophenyl)-5-propyI-1 H-pyrazol-4-yl]methy 1} -
amino)methyl]cyclohexyl}-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoiine-2,4-diamine;
N"-{cis-4-[2-(4-bromo-2-trifluoromethoxy-phenyl)-ethylamino]-cyclohexyl}-
N4,N4-dimethyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine;
N2-{cis-4-[2-(4-bromo-2-trifluoromethoxy-phenyl)-ethylamino]-cyclohexyl}-N4-
methyI-5,6,7,8-tetrahydro-quinazoline-2,4-diamine;
N"-{cis-4-[(4-bromo-2-trifluoromethoxy-benzyl)amino-methyl]-cyclohexyl}-N4-
methyI-5,6,7,8-tetrahydro-quinazoIine-2,4-diamine;
N2-{cis-4-[(4-bromo-2-trifluoromethoxy-benzyl)amino-methyl]-cyclohexyl}-
N+,N4-diraethyl-5;6,7?8-tetrahydro-quinazoIine-2,4-diamine;
N4,N4-dimethyl-N2-{cis-4-[(2-trifluoromethoxy-benzyi)amino-methyl]-
cyC1-5hexy!}-5,6,7,8-tetrahydro-quinazoline-2,4-diamine; and
N -methyl-N -{cis-4-[(2-trifluoromethoxy-benzyl)amino-methyl]-cyC1-5hexyl}-
5,6,7,8-tetrahydro-quinazoline-2,4-diamine;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
15. The compound according to claim 34 selected from the group consisting of:

925
N2-(cis-4-{[(5-methoxy-lH-indol-3-yl)methyl]amino}cyclohexy!)-N4,N4-dimethyl-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
ethyl 4,6-dichIoro-3-{[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)amino]methyl}-lH-indole-2-carboxylate;
N2-[cis-4-( {[3-(4-fluorophenyl)-1 H-pyrazol-4-yl]methyl} amino)cyclohexyl]-
N4,N4-dimethyI-5,6,7,8-tetrahydroquinazotine-2,4-diamine;
3-[{2-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolm-2-
yl]amino}cyclohexyi)amino]ethyl}(phenyl)amino]propanenitrile;
N-{(lS)-l-benzyl-2-[(cis-4-{[4-(dimethylamino)-5,657,8-tetrahydroquinazolin-2-
yl]araino}cyC1-5hexyl)amino]ethyl}-4-methylbenzenesulfonamide;
N2-[cis-4-({[l-(diphenylmethyl)azetidin-3-yl]methyI}amino)cyclohexyl]-N4,N4-
dimethyI-5,6;7,8-tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(2,6-dimethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-dimethyl-
5,6,7J8-tetrahydroquinazoline-2,4-diamine;
N2-[cis-4-({[(5-methoxy-lH-indol-3-yI)methyI]amino}methyl)cyclohexyl]-N4,N4-
dimethy 1-5,6,7,8 -tetrahydroquinazoline-2,4-diamine;
N2-[cis-4-({[(5-bromo-lH-indol-3-yl)methyl]amino}methyi)cyclohexyl]-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(3-ethoxy-4-methoxybenzyI)amino]methyl}cyclohexyl)-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
4-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyl]amino}methyl)-2-iodo-6-methoxyphenol;
N2-(cis-4-{[(3,3-diphenyIprop-2-en-l-yl)amino]methyl}cyclohexyl)-N4,N4-
d imethy 1-5,6,7,8-tetrahydroqu inazol ine-2,4-d i am i ne;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,6-trimethoxybenzyl)amino]methyl}-cyclohexyl)-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N2-(cis-4-{[(2,5-diethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-dimethyl-
5,6,7,8 -tetrahydroqui nazol ine-2,4 -d iam ine;

926
N2-(cis-4-{[(2,4-diethoxybenzyl)amino]methyl}cyclohexy])-N4,N4-dimethyi-
5,6,7,8-tetrahydroqu inazo I ine-2,4-di am ine;
N"~(cis-4-{[(3,5-dibromo-2-methoxybenzyl)amino]methyI}cyC1-5hexyI)-N4,N4-
dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N ,N -dimethyl-N"-(cis-4-{[(2,4,5-triethoxybenzyl)amino]methyl}-cyclohexyl)-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-trimethoxybenzyl)amino]methyI}-cyclohexyl)-
5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N4,N4-dimethyl-N2-[cis-4-({[(l-phenyl-5-propyI-lH-pyrazol-4-
yl)methyl]amino}methyl)cyclohexyl]-5,6,7,8-tetrahydroquinazoline-2,4-diamine;
N2-{cis-4-[({[l-(4-chloropheny])-5-propyI-lH-pyrazol-4-yl]methyl}-
amino)methyl]cyclohexyl}-N4,N4-dimethyI-5,6,7,8-tetrahydroquinazoIine-254-diamine;
N"-{cis-4-[2-(4-bromo-2-trifIuoromethoxy-phenyl)-ethylamino]-cyclohexyI}-
N4,N4-dimethyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine;
N2-{cis-4-[(4-bromo-2-trifluoromethoxy-benzyI)amino-methyl]-cyclohexyl}-N4-
methyI-5,657,8-tetrahydro-quinazoIine-2,4-diamine;
N2-{cis-4-[(4-bromo-2-trifluoromethoxy-benzyl)amino-methyl]-cyC1-5hexyl}-
N4,N4-dimethyl-556,7,8-tetrahydro-quinazoline-2,4-diamine; and
N4,N4-dimethyl-N2-{cis-4-[(2-trifluoromethoxy-benzyl)amino-methyl]-
cyC1-5hexyl}-5,6,7,8-tetrahydro-quinazoline-2,4-diamine;
or a pharmaceuticalIy acceptable salt, hydrate, or solvate thereof.
36. The compound according to claim 29 wherein Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
"OXO,
•C1-5 alkoxy,

927
•C1-5 alkoxy substituted by carbocyclic aryl,
•C1-5 alkylcarbonyloxy,
•carbocyclic aryioxy,
•carbocyclic aryioxy substituted by halogen,
•carbocyclic aryioxy substituted by nitro,
•heterocyclyloxy,
•heterocyclyloxy substituted by C1-5 alkyl,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•carbocyclic arylcarbonylamino,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by substituent(s) independently selected from
the group consisting of:
••carbocyclic aryl, and
••carbocyclic aryl substituted by substituent(s) independently
selected from the group consisting of:
—halogen, and
•••C1-5 alkoxy,
•carbocyclic arylthio,
•heterocyclylthio,
•heterocyclylthio substituted by C1-5 alkyl,
•C3-6 cycloalkyl,
•C3-6 cycloalkenyl,
•carbocyclyl,
•carbocycly! substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
"C1-5 alkyl,

928
••C1-5 alkoxy,
••C2-5 alkenyl, and
"C7.5 alkenyj substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and
•••carbocyclic aryl substituted by Cj.5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
"hydroxy,
••nitro,
"CU5 alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
—oxo,
•••carbocyclic aryl, and
"•heterocyclyl,
"C1-5 aikoxy,
••C1-5 alkoxy substituted by halogen,
•*C^5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryloxy,
••mono-carbocyclic arylaminocarbonyl,
••mono-carbocyclic arylaminocarbonyl substituted by halogen,
••di-carbocyclic arylaminocarbonyl,
••di-carbocyclic arylaminocarbonyl substituted by halogen,
••carbocyclic aryl, and
"•heterocyclyl,

929
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
"C1-5 alkyl,
••C1-5 alkoxy,
••C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryl, and
••carbocyclic aryl substituted by halogen,
(ii) C2.5 alkenyl, and
C2-5 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
"carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
••nitro,
(iii) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••oxo, and
••carbocyclic aryl,
•carbocyclic aryl,
(iv) carbocyclyl,
(v) carbocyclic aryl, and

930
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
■C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
"OXO,
••carbocyclic aryloxy,
••carbocyclic aryl, and
••carbocyclic aryl substituted by C1-5 alkyl,
•C1-5 aikoxy,
•Cj-5 aikoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 aikoxy,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•amino,
•mono-Ct_5 alkylamino,
•di-C1-5 alkylamino,

931
•C?-5 alkynylcarbonylamino,
•C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,
•(carbocyclic aryl)NHC(O)NH,
•(carbocyclic aryI)NHC(O)NH substituted by C1-5 alkoxy,
•(carbocyclic aryl)NHC(O)NH substituted by haloganated C1-5 alkoxy,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by halogen,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by cyano,
•mono-C1-5 aikylaminosulfonyl,
•di-C1-5 alkylarainosulfonyl,
•carbocyclic aryl,
•heterocyclyl,
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of;
••C^ alkyl,
••carbocyclic aryl, and
••halogenated carbocyclic aryl,
(vi) heterocyclyl, and
heterocyclyi substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C1-5 alkylthio,

932
"Cj_5 alkylthio substituted by carbocyclic aryl,
••C1-5 alkylthio substituted by halogenated carbocyclic aryl,
••carbocyclic aryl,
••carbocyclic aryl substituted by halogen, and
••heterocyclyl,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C\s alkyl,
•C1-5 alkylthio,
•C2-5 alkenylthio,
•carbocyclic arylthio,
•Cs.5 alkylsulfonyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by C1-5 alkyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
••Cj.g alkyl,
•heterocyclyl;
L is Formula (VII);
Y is -C(O)s
wherein carbocyclic aryl is phenyl, naphthyl, or anthranyl;
carbocyclyl is 1,2,3,4-tetrahydronaphthyI, 1-oxo-indanyl, 9-oxo-9H-
fluorenyl, or indenyl;
heterocyclyl is 1,2,3-triazolyl, l/f-indolyl, l//-pyrrolyl, 2,3-dihydro-l-
oxo-isoindolyl, 2,4-dihydro-3-oxo-pyrazolyl, 2//-benzopyranyl, 2-oxo-

933
benzopyranyl, 4-oxo-l,5,6,7-tetrahydro-indolyl, 9//-xanthenyl, benzo[l,3]dioxolyl,
benzo[2,l,3]oxadiazolyl, benzo[l,2,5]oxadiazolyl, benzo[b]thienyl, benzofury],
benzothiazolyl, furyl, isoxazolyl, morpholino, pyrazolyl, pyridyl, pyrimidyl,
quinolyl, quinoxalyl, thiazolyl, orthienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
37. The compound according to claim 36 wherein R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
38. The compound according to claim 37 wherein Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•C1-5 alkylcarbonyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•mono-Cu alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•carbocyclic aryicarbonylamino,
•C1-5 alkyhhio,
"C1-5 alkylthio substituted by substituent(s) independently selected from
the group consisting of:
••carbocyclic aryl, and

934
••carbocyclic aryl substituted by halogen,
•heterocyclylthio,
•heterocyclylthio substituted by C1-5 alkyl,
•C3-6 cycloalkyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
"d.s alkyl,
••C2.5 alkenyl, and
••C2-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•'•carbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••nitro,
••C1-5 alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••oxo, and
•••heterocyclyl,
••C1-5 alkoxy,
"•carbocyclic aryloxy,
••carbocyclic aryl, and

935
••heterocyclyl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••C,_5 alkyl,
••C1-5 alkoxy, and
••carbocyclic aryl,
(ii) C2-5 alkenyl, and
C2.5 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by nitro,
(iii) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by carbocyclic aryl,
(iv) carbocyclyl,
(v) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
•C,.s alkyl,
•Cu alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
'•oxo, and
••carbocyclic aryl,

936
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5- alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C[.5 alkylaminocarbonyl substituted by carbocyclic aryl,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•C2.5 alkynylcarbonylamino,
•C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,
•(carbocyclic aryl)NHC(O)NH,
•(carbocyclic aryl)NHC(O)NH substituted by C1-5 alkoxy, and
•(carbocyclic aryI)NHC(O)NH substituted by haloganated C1-5 alkoxy,
(vi) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C1-5 alkylthio,

937
•*C1-5 alkylthio substituted by carbocyclic aryl,
••C1-5 alkylthio substituted by halogenated carbocyclic aryl,
••carbocyclic aryl, and
••heterocyclyl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkyl,
•C1-5 alkylthio,
"carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
"C1-5 alkyl,
•heterocyclyl;
wherein carbocyclic aryl is phenyl;
carbocyclyl is I-oxo-indanyl or indenyl;
heterocyclyl is 1,2,3-triazolyl, l//-indolyl, \H-pyno\y\, 2,3-dihydro-l-
oxo-isoindolyl, 2-oxo-benzopyranyi, benzo[2,l,3]oxadiazolyl,
benzo[l,2,5]oxadiazolyl? furyl, isoxazolyl, morpholino, pyrazoly!, pyridyl,
pyrimidyl, quinolyl, quinoxalyl, thiazolyl, or thienyl;
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
39. The compound according to claim 38 wherein Rt is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•oxo,

938
•C1-5 alkylcarbonyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•carbocyclic arylcarbonylamino,
•carbocyclyl,
•carbocyclyi substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
•-C.5 alkyl,
"C2-s alkenyl, and
••C2.5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and
—carbocyclic aryl substituted by C1-5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
••nitro,
••C1-5 alkyl, and
"C1-5 alkoxy,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
"C1-5 alkyl,

939
•*C1-5 alkoxy, and
••carbocyclic aryl,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
"•halogen, and
••oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-d-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•C2-5 alkynylcarbonylamino,
•C?-5 alkynylcarbonylamino substituted by carbocyclic aryl,
•(carbocyclic aryI)NHC(O)NH,
•(carbocyclic aryl)NHC(O)NH substituted by C1-5 alkoxy, and
•(carbocyclic aryl)NHC(O)NH substituted by haloganated C1-5 alkoxy,
(iii) heterocyclyl, and

940
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alky],
•C1-5 alkyl substituted by halogen,
•C1-5 alkyl substituted by heterocyclyl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkyl,
•C1-5 alkylthio,
•carbocyclic aryl,
•carbocyclic aryl substituted by halogen, and
•carbocyclic aryl substituted by nitro;
wherein carbocyclic aryl is phenyl;
carbocyclyl is indenyl;
heterocyclyl is l//-indolyl, 1/f-pyrrolyl, 2-oxo-benzopyranyl,
benzo[2,l,3]oxadiazolyl, benzo[l,2,5]oxadiazolyl, furyl, isoxazolyl, morpholino,
pyridyl, quinoxalyl, orthienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
40. The compound according to claim 1 selected from the group consisting of:
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexy!)-3-methoxybenzamide;
3-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,758-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)benzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y l]amino} cyclohexyl)benzamide;

941
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yi]amino}-
cyclohexyl)-2,l,3-benzoxadiazole-5-carboxamide;
3-chloro-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)benzamide;
4-chloro-N-(cis-4-{[4-(dimethylamino)-5:,6,7,8-tetrahydroquinazolin-2-
yl]amino} cyclohexyl)benzamide;
4-chloro-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-3-nitrobenzamide;
2-(4-chIorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)acetamide;
3-cyano-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)benzamide;
3,5-dichloro-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)benzamide;
3,4-dichIoro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino} cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2,2-diphenylacetamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyl)-3,4-difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-3,5-difluorobenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyI)-4-fluorobenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoiin-2-yl]amino}-
cyclohexyl)~3-fluoro-5-(trifluoromethy])benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cy c 1 ohexy I)hexan am ide;

942
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquina2olin-2-yI]amino}-
cyclohexyl)-4-methyl-3-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-3-nitrobenzamide;
(2R)-N-(cis-4-{[4-(dimethyIamino>5,6,7,8-tetrahydroquinazolin-2-
y]]amino}cyclohexyI)-2-phenylcyC1-5propanecarboxamide;
N-(cis-4- {[4-(dimethyIamino)'5,6,7,8-tetrahydroquinazolin-2-yl]amino} -
cyc!ohexyl)-2-phenoxybutanamide;
N-(cis-4- {[4-(dimethylamino)-5,6,758-tetrahydroquinazolin-2-y ljamino} -
cyclohexy I )-2 -phenoxypropanamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-3-methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyc!ohexyl)-4-methylbenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-3-(trifIuoromethoxy)benzamide;
4-bromo-N-(cis-4-{[4-(dimethy]amino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-3-methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyI)-3-iodobenzamide;
2-chIoro-N-(cis'4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyt)-4-fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-(3-methoxyphenyl)acetamide;
N-(cis-4-{[4-(dimethyIamino)-5,657,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyl)-2-(4-fluorophenyI)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyl)-2-(4-methoxyphenyl)acetamide;

943
N-(cis-4-{[4'(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyl)-5-methyI-2-(trifluoromethyl)-3-furamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyl)-2,5-dimethyl-3-furamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yI]amino}cyclohexyl)-4-fluorobenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-yI]amino}-
cyclohexyl)-3-fluoro-4-methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-3,5-dimethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyl)-3,5-bis(trifluoromethyI)benzamide;
N-Ccis^-l^-tdimethylaminoyS^^^-tetrahydroquinazolin^-y^amino}-
cyclohexyl)-4-fluoro-3-methylbenzamide;
2,5-dichloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yI]amino}cyclohexyl)thiophene-3-carboxamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-(propylthio)nicotinamide;
l-benzyi-3-tert-butyl-N-(cis-4-{[4-(dimethylamino)-5,6,7;8-tetrahydroquinazolin-
2-yI]amino} cyclohexyl)-1 H-pyrazoIe-5-carboxamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)nicotinamide;
2-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)amino]-2-oxo-l-phenylethyl acetate;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)benzamide;
2-(benzyloxy)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)acetamide;

944
2-(4-chlorophenoxy)-N-{cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yl]amino}cyclohexyl)acetamide;
3-(2-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)-5-methyIisoxazoIe-4-carboxamide;
l-(4-chIorophenyI)-N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)cyclopentanecarboxamide;
3-(2-chloro-6-fluorophenyl)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahyd roqui nazo I in-2 -y 1] amino} eye lohexy 1)- 5 -methy 1 i soxazole-4 -carboxam ide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyl)-l,3-dimethyI-IH-pyrazoIe-5-carboxamide;
N-(cis-4-{[4-(dimethylamino>5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-3-fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6!7,8-tetrahydroquinazolin-2-yl]amino}-
cyc!ohexyI)-4-f!uoro-3-(trifluoromethyl)benzaraide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyI)-5-methyl-2-phenyI-2H-l,2,3-triazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-(4-methoxyphenoxy)-5-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexy 1)- 5 -nitro-2 -furam ide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyc!ohexyl)-2-phenoxyacetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyc lohexy l)quinoxa!ine-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexy!)-3-(trifluoromethyl)benzamide;
2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-y!]amino}cyC1-5hexyl)acetamide;

945
3-(2,6-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)-5-methylisoxazoIe-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cy c lohexy 1 )-2 -phenoxyn i cotinam i de;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
eye lohexyl)-2-(4-methyl phenoxy)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyI)-2-(2-thienyI)-l,3-thiazole-4-carboxamide;
5-bromo-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
y]]amino}cyclohexyl)thiophene-2-carboxamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-(2,3,6-trichlorophenyI)acetamide;
2-(2-chloro-4-fluorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)acetamide;
5-(4-chloro-2-nitrophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)-2-furamide;
5-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)thiophene~2-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyc lohexy l)-2,3 -diphenylpropanamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,84etrahydroquinazolin-2-yI]amino}-
cyclohexyl)-3-(2-hydroxyphenyI)propanamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyc!ohexyI)-5-iodo-2-ftiramide;
N-(cis-4~{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-yI]amino}-
cyc!ohexyl)-2-(2-iodophenyI)acetamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-y]]amino}-
cyclohexyl)-2-(5-methoxy-2-methyl-IH-indol-3-yl)acetamide;

946
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-3-oxoindane-I-carboxamide;
2-benzyI-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yljamino} cyc!ohexyl)benzamide;
2,2-bis(4-chlorophenyi)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyl)-5-(4-methyl-2-nitrophenyl)-2-furamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyc lohexy 1)- 5 -nitrothiophene-2 -carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyI)-3-methyl-4-nitrobenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-3-methoxy-4-nitrobenzamide;
3-acetyl-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)benzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-furamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-[(4-methylpyrimidin-2-yl)thio]acetamide;
5-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyc!ohexyl)-2-furamide;
2-(3,4-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-(4-hydroxy-3,5-dimethoxyphenyl)acetamide;
4,5-dibromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)thiophene-2-carboxamide;

947
N2,N -dibenzoyl-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazo!in-2-
yl]amino}cyclohexyl)lysinamide;
3-(dimethylamino)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino} cyclohexyl)benzamide;
4,5-dibromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyl)-2-furamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yI]amino}-
cyc I ohexy l)-4-(4-fl uoropheny l)-4 -oxobutan am ide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7:,8-tetrahydroquinazolin-2-yl]amino}-
cy c lohexyl )-2 -(2 - fl uorob ipheny 1-4-y l)propanam ide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-[4-( 1 -oxo-1,3-dihydro-2H-isoindoI-2-yl)phenyI]propanamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-(lH-indol-3-yl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyc!ohexyl)-2-(lH-indol-3-yI)-4-oxo-4-phenylbutanamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazo!in-2-yl]amino}-
cyclohexyl)-3,5-dimethyl-2-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-
benzamide;
3,5-dichloro-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-[(3-phenyIprop-2-ynoyI)amino]benzamide;
4-(4-tert-butylphenyI)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yl]amino}cyclohexyl)-2-(7-ethyI-IH-indol-3-yl)-4-oxobutanamide;
N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexy l)-2-( 1 -methyl-1 H-indol-3-y I)-4-(4-methylphenyI)-4-oxobutanamide;

948
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyl)-2-methyl-l-(3-morpholin-4-ylpropyI)-5-phenyl-lH-pyrrole-3-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyc lohexy l)-4-(4 -n itropheny l)butanam i de;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyl)-2-(3-phenoxyphenyl)acetamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquina2olin-2-yI]amino}-
cyclohexyl)-2-(4-phenoxyphenyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-(2-phenyl-1 H-indol-3-yl)acetamide;
N2-benzoyI-N5-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yljaminoJcyclohexy^-N^N'-dipropylglutamamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyC1-5hexyI)-3-phenoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-(ethylthio)-2,2-diphenylacetamide;
N'-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyI)-N,N-bis[(lS)-l-phenylethyl]phthalamide;
(2S)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyC1-5hexyl)-2-(2-f!uorobiphenyl-4-yl)propanamide;
2-[(4-chlorobenzyl)thio]-N-(cis-4-{[4-(dimethylamino)-5!6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)-4-(4-methylphenyl)-4-oxobutanamide;
N-(cis-4-{[4-(dimethylamino)-5T6,7,84etrahydroquinazolin-2-y]]amino}-
cyclohexy!)-2-{(lE)-5-f!uoro-2-methyI-l-[4-(methylsulfinyl)benzylidene]-lH-inden-3-
yl}acetamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyc lohexy l)-2-[4-(2-thienylcarbonyI)phenyl]propanamide;

949
3-(benzyIoxy)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)-4-methoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyI)-2-methyl-l,5-diphenyl-lH-pyrroIe-3-carboxamide;
l-{2-[(2-chloro-6-fluorobenzyl)thio]ethyl}-N-(cis-4-{[4-(dimethylamino)-5,6,7,i
tetrahydroquinazoIin-2-yI]amino}cyclohexyl)-2-methyl-5-pheny]-lH-pyrrole-3-
carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-phenoxybenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyI)-2-phenyIquinoIine-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-5-(3-nitrophenyI)-2-furamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-y)]araino}-
cy c lohexyl)-5 -nitroth iophene-3 -carboxam ide;
N-(cis-4-{[4-tdimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexy!)-l-methyl-4-nitro-lH-pyrrole-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-methoxy-4-nitrobenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cy c lohexy l)-2-methoxy-2 -pheny lacetam ide;
5-chloro-N-(cis-4-{[4-(dimethy]amino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)-2-hydroxybenzamide;
3-bromo-N-[(cis-4-{[4-(dimethyIamino)-5,65758-tetrahydroquinazo!in-2-
yl]amino}cyclohexyl)methyl]benzamide;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyc!ohexyi)methyl]-2-(ethylthio)nicotinamide;

950
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyl)methyl]-2-(4-methoxyphenyl)acetamide;
N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)methyl]-5-methyl-2-(trifluoromethyl)-3-furamide;
(2E)-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yi]amino}cyclohexyl)methyl]-3-(4-nitrophenyl)acrylamide;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyi)methyI]-4-fluoro-3-methylbenzamide;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyl)methyl]-2-(propylthio)nicotinamide;
2,6-dichIoro-N-[(cis-4-{[4-(dimethy)amino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)methyl]benzamide;
N-[(cis-4-{[4-(dimelhylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyC1-5hexyl)methyl]-2,4,6-trimethylbenzamide;
2-chloro-N-[(cis^-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)methyI]-6-fluorobenzamide;
2,4,6-trichloro-N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yi]amino}cyclohexyl)methyl]benzamide;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyI)methyl]-2-(2,356-trich]orophenyl)acetamide;
(2E)-N-[(cis-4-{[4-(dimethy!amino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)methyl]-3-(3-nitrophenyI)acrylamide; and
N-[cis-4-(4-dimethylamino-5,6,7,8-tetrahydro-quinazolin-2-ylamino)~
cyclohexylmethyl]-3,4-difluorQ-benzamide;
or a pharmaceuticalty acceptable salt, hydrate, or solvate thereof.
41. The compound according to claim 40 selected from the group consisting of:

951
N-(cis-4-{[4-(dimethylamino)"5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyI)-3-methoxybenzamide;
3-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(diraethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyl)-2,1,3-t>enzoxadiazoIe-5-carboxamide;
3-chloro-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)benzamide;
4-chIoro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y l]amino} cyclohexyl)benzamide;
4-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-3-nitrobenzamide;
2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y l]amino} cyclohexyl)acetamide;
3-cyano-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yljamino} cyclohexyl)benzamide;
355-dichloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)benzamide;
3,4-dichloro-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino} cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyl)-2,2-diphenylacetamide;
N-(cis-4-{[4-(diraethylamino)-5,6?7r8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyI)-3,4-ditluorobenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-y]]amino}-
cyclohexyl)-3,5-difluorobenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexy!)-4-fluorobenzamide;

952
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyl)-3-fluoro-5-(trifluoromethyI)benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-4-methyl-3-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cy c lohexy l)-3 -n itrobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyl)-2-phenoxybutan amide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyc lohexy I )-2-phenoxypropanamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-3-methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyI)-3-iodobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-(4-fluorophenyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyl)-2,5-dimethyl-3-furamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yI]amino}cyclohexyI)-4-f!uorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyl)-3,5-dimethoxybenzamide;
N-(cis-4-{[4-(dimethyIamino)-5?6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-3,5-bis(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-yI]amino}-
cyclohexy])-4-fluoro-3-methylbenzamide;
2,5-dichloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyf)thiophene-3-carboxamide;

953
5-bromo-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2'
yl]amino}cyclohexyl)nicotinamide;
2-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyl)amino]-2-oxo-1 -phenylethyl acetate;
3-(2-chIoro-6-fluorophenyI)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyC1-5hexyl)-5-methylisoxazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyc 1 ohexy l)-3 -fluoro benzamide;
N-(cis-4'{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-4-fluoro-3-(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-(4-methoxyphenoxy)-5-nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cycl ohexy I )-5 -n itro-2 -furam ide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyc 1 ohexy l)-2 -phenoxy acetami de;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazotin-2-yl]amino}-
cyclohexyI)quinoxaIine-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyI)-3-(trtfIuoromethyl)benzamide;
2-(3-chIorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8"tetrahydroquinazolin-
2-yl] ami no} cyclohexyl)acetam ide;
3-(2,6-dichIorophenyl)-N-(cis-4-{[4-(dimethyiamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyI)-5-methylisoxazoIe-4-carboxamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyI)-2-(4-methylphenoxy)nicotinamide;
2-(2-chIoro-4-fIuorophenyI)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroqumazoIin-2-yI]amino}cyclohexyl)acetamide;

954
5-(4-chloro-2-nitrophenyI)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)-2-furamide;
5-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)thiophene-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-5-iodo-2-furamide;
2,2-bis(4-chlorophenyl)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyl)-5-nitrothiophene-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-3-methyl-4-nitrobenzamide;
N-(cis-4-{[4-{dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexy!)-3-methoxy-4-nitrobenzamide;
3-acetyl-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)benzamide;
5-bromo-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-furamide;
5-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-furamtde;
2-(3,4-dichlorophenyI)-N-(cts-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-(4-hydroxy-3,5-dimethoxyphenyl)acetamide;
4,5-dibromo-N-(cis-4-{[4-(dimetbylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]araino}cyclohexyI)-2-furamide;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazo)in-2-yl]amino}-
cyclohexyl)-2-(lH-indo!-3-yI)acetamide;

955
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yI]amino}-
cyclohexyl)-2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetamide;
N-Ccis^-l^-tdimethylaminoyS^^S-tetrahydroquinazoIin^-ylJamino}-
cyclohexyl)-3,5-dimethyl-2-[({[4-(trif!uoromethoxy)phenyl]amino}carbonyl)amino]-
benzamide;
3,5-dichIoro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)-2-[(3-phenylprop-2-ynoyI)amino]benzamide;
4-(4-tert-butylphenyl)-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-
2-yl]amino}cyclohexyl)-2-(7-ethyl-lH-indol-3-yi)-4-oxobutanamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-methyl-l-(3-morpholin-4-yipropyl)-5-phenyl-lH-pyrrole-3-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyl)-4-(4-nitrophenyl)butanamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-(2-phenyl-lH-indol-3-yl)acetamide;
N2-benzoyI-N5-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
y^aminoJcyC1-5hexylJ-N^N^dipropylglutamamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-3-phenoxybenzamide;
N'-(cis-4-{[4-(dimethyIamino)-5,6?7;,8-tetrahydroquinazolin-2-yl]am[ino}-
cyclohexy ))-N,N-bis[( 1S)-1 -phenylethyljphthalamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyI)-2-{(lE)-5-fluoro-2-methyl-l-[4-(methylsulfiny])benzylidene]-lH-inden-3-
yl}acetamide;
3-(benzyloxy)-N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyI)-4-methoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-2-phenoxybenzamide;

956
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyl)-5-nitrothiophene-3-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyl)-1 -methyl-4-nitro-1 H-pyrrole-2-carboxamide;
5-chloro-N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yI]amino}cyclohexyl)-2-hydroxybenzamide;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)methyl]-2-(ethyIthio)nicotinamide;
N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyC1-5hexyl)methyl]-2-(4-methoxyphenyl)acetamide;
N-[(cis-4-{[4-(dimethylamino)-556?7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)memyl]-5-methyl-2-(trifluoromethyl)-3-furamide;
N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyi)methyi]-2-(propyIthio)nicotinamide; and
2,4,6-trichlorO"N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-
yl]amino}cyclohexyl)methyl]benzamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
42. The compound according to claim 29 wherein Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•oxo,
•C1-5 alkoxy carbonyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,

957
••Chalky!,
••C2.5 alkenyl, and
"C,_5 alkoxy,
•C|_5 alkylthio, and
•heterocyclyl,
(ii) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by carbocyclic aryl,
(iii) carbocyclyl,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•cyano,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••oxo, and
'•carbocyclic aryl,
•C1-5 alkoxy carbonyl,
•C1-7 alkoxy,
•C1-7 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••carbocyclic aryl,
*C3-6 cycloalkoxy,
•carbocycHc aryloxy,

958
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by halogen, and
•carbocyclic aryl,
(v) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•Q.5 alkyl,
•Cj_5 alkyl substituted by halogen,
•C1-5 alkoxy carbonyl
•Ci-s alkoxy carbonyl substituted by carbocyclic aryl, and
•carbocyclic aryl;
L is Formula (VII);
Y is -C(O)NR5-;
wherein carbocyclic aryl is phenyl or naphthyl;
carbocyclyl is indanyl, adamantly, or 9/f-fluorenyl;
heterocyclyl is 2,3-dihydro-benzo[l,4]dioxinyl, 3,4-dihydro-2/f-
benzo[b][l.,4]dioxepinyl, 4//-benzo[l,3]dioxinyl, benzo[l,3]dioxolyl, furyl,
isoxazolyl, piperidyl, pyridyl, or thienyl;
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
43. The compound according to claim 42 wherein R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-: R5 is hydrogen;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.

959
44. The compound according to claim 43 wherein R! is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkoxy carbony],
•carbocyclic aryl, and
•carbocyclic aryl substituted by halogen,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•nitro,
•C,_s alkyl,
•Cj.5 alkyl substituted by halogen,
•C1-5 alkoxy, and
•C1-5 alkoxy substituted by halogen,
(iii) heterocyclyl, and
heterocyclyl substituted by C^ alkyl, and
heterocyclyl substituted by carbocyclic aryl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is isoxazolyl;
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
45. The compound according to claim 1 selected from the group consisting of:
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-N'-(2-ethyl-6-methylphenyl)urea;

960
N-(cis-4-{[4-(dimethylamino)-5,6,7,84etrahydroquinazolin-2-yI]amino}-
cyC1-5hexyl)-N'-(4-fluorophenyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-N'-mesitylurea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyl)-N'-(2,4,6-trichlorophenyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-N'-(2,4,6-tribromophenyI)urea;
N-(2,4-dibromo-6-fluorophenyl)-N'-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea;
N-(2,6-diethyIphenyI)-N'-(cis-4- {[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)urea;
N-(2-chlorobenzyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyc!ohexyI)-N'-(2-ethyl-6-isopropylphenyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyl)-N'-(2-ethylphenyl)urea;
N-Ccis^-l^-tdimethylaminoJ-S^^^-tetrahydroquinazolin^-ylJamino}-
cyclohexyl)-N'-(2-isopropyI-6-methylphenyl)urea;
N-(2-tert-butyl-6-raethylphenyl)-N'-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyC1-5hexyl)urea;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyl)-N'-(dipheny!methyI)urea;
N-(4-bromo-2,6-dimethyIpheny])-N'-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-N'-(3-methyI-5-phenylisoxazol-4-yl)urea;

961
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-N'-l -naphthylurea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-y]]amino}-
cyclohexyl)-N'-[ 1 -(1 -naphthyi)ethy l]urea;
N-(2,4-dibromophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyC1-5hexyl)urea;
N-(2,4-dichlorobenzyl)-Nt-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)urea;
N-(2,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-N'-(2-ethoxyphenyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyl)-N'-(2-f!uorobenzyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyc]ohexyI)-N'-(3,4,5-trimethoxyphenyl)urea;
N-(3,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea;
N-(4-chIoro-2-methylphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyC1-5hexyl)urea;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyI)-N'-(4-fluorobenzyl)urea;
N-(cis^-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-N'-(4-methoxy-2-methylphenyl)urea;
N-(5-chIoro-2,4-dimethoxyphenyl)-N'~(cis-4-{[4-(dimethylamino)-5,6,7,J
tetrahydroquinazolin-2-yl]amino}cyc!ohexyl)urea;
N-[l-(4-bromophenyI)ethyl]-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea;

962
N-(4-bromo-2-methy]phenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea;
N-fcis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-N'-(5-methyI-3-phenyIisoxazol-4-yl)urea;
N-(2,3-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazoIin-2-yl]amino}-
cyclohexyI)-N'-(4-methylphenyI)urea;
N-(2,6-diisopropylphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-N'-(2,4,5-trichlorophenyl)urea;
N-(2,5-dimethoxyphenyl)-N'-(cis-4-{[4-tdimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)urea;
N-(4-bromo-2-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyI)urea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-
yl]amino}cyclohexy!)-N'-[2-(trifluoromethoxy)phenyI]urea;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)methyl]-N'-(2,6-dimethyIphenyl)urea;
N-(2,4-difluorophenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)methyl]urea;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)methyl]-N'-(2-ethy!-6-methylphenyI)urea;
ethyl N-({[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]-
amino}cyclohexyl)methyl]amino}carbonyl)leucinate;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyl)methyl]-N'-(4-fluorophenyl)urea;

963
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyl)methyl]-N'-mesitylurea;
N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)methyI]-N'-(2,4,6-trichlorophenyl)urea;
N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-y]]araino}-
cyclohexyl)methyI]-N'-(2,4,6-tribromophenyl)urea;
N-(2,6-diethylphenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyI]urea;
N-[2-chloro-6-(trifluoromethyl)phenyl]-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,i
tetrahydroquinazolin~2-yl]amino}cyclohexyl)methyl]urea;
N-(2-chloro-6-methylphenyI)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]urea;
N-[(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)methyi]-N'-(2-ethyl-6-isopropyIphenyl)urea;
N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyI)methyl]-N'-(2-isopropyI-6-methyIphenyl)urea;
N-(2-tert-butyl-6-methylphenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyI]urea;
N-(2-tert-butyIphenyl)-N'-[(cis-4-{[4-(dimethylamino)-556,7,8-
tetrahydroquinazoIin-2-yl]amino}cyC1-5hexyl)methyl]urea;
N-(3-chIoro-2-methylphenyl)-N'-[fcis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]urea;
N-(4-bromo-2,6-dimethylphenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yt]amino}cyclohexyI)methyl]urea;
N-(2,6-diisopropylphenyI)-N'-[(cis-4-{[4-(dimethy]amino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)methyl]urea;
N-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)methyI]-N'-(2,3-dimethyI-6-nitrophenyl)urea;

964
N-(2,6-dibromo-4-fluorophenyI)-N'-[(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino} eye lohexyl)methyl] urea;
N-(2,6-dichlorophenyl)-N'-[(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)methyl]urea; and
l-(2,3-dichloro-phenyl)-3-[cis-4-(4-diraethylamino-5,6,7,8-tetrahydro-quinazolin-
2-ylamino)-cyC1-5hexylmethyl]-urea;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
46. The compound according to claim 29 wherein R] is selected from the group consisting of:
(i) Ci-g alkyl, and
Ci-g alkyl substituted by substituent(s) independently selected from the
group consisting of:
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
*C3^6 cycloalkyl,
•C3-6 cycloalkenyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
••Ci.s alkoxy,
•heterocyclyl,
(ii) C2-5 alkynyl,
(iii) C2-5 alkenyl,
(iv) C3_]2 cycloalkyl,
(v) carbocyclyl,
(vi) carbocyclic aryl, and

965
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•cyano,
•nitro,
•C1-50 alkyl,
•Ci-io alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••oxo,
•carboxy,
•C1-5 alkoxy carbonyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
"halogen, and
"carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by nitro,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•C1-5 alkoxy carbonylamino,
•carbocyclic aryl azo,
•carbocyclic aryl azo substituted by substituent(s) independently selected
from the group consisting of:
••mono-C1-5 alkylamino, and
••di-C1-5 alkylamino,
•C1-5 alkylthio,

966
•C1-5 alkylthio substituted by halogen,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by nitro,
•amino sulfonyl,
•heterocyclyl sulfonyl,
•C3-6 cycloalkyl,
•C3-6 cycloalkyl substituted by C1-5 alkyl,
•carbocyclic aryl, and
•heterocyclyl,
(vii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkyl,
•C1-5 alkoxy carbonyl,
•carbocyclic aryloxy,
•carbocyclic aryl, and
•heterocyclyl;
L is Formula (VII);
Y is -C(S)NR5-;
wherein carbocyclic aryl is phenyl or naphthyi;
carbocyclyl is indanyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.1]heptenyl, or
adamantly;
heterocyclyl is 2,3-dihydro-benzo[l,4]dioxinyl, 4,5,6,7-tetrahydro-
benzo[b]thienyl, benzo[l,3]dioxolyl, benzo[2,l,3]thiadiazolyl, furyl, isoxazolyl,
morpholinyl, oxazolyl, phenanthro[9,10-d]oxazolyl, piperidyl, pyrazolyl, pyridyl,
tetrahydrofuryl, orthienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.

967
47. The compound according to claim 46 wherein R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-: R5 is hydrogen;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
48. The compound according to claim 47 wherein Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by carbocyclic aryl,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•Ci.s alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by halogen,
•mono-C1-5 alkylamino, and
*di-C1-5 alkylamino;
wherein carbocyclic aryl is phenyl or naphthyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
49. The compound according to claim 1 selected from the group consisting of:
N-(2,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yI]amino}-
cyclohexyl)-N'-(3,4,5-trimethoxyphenyl)thiourea;

968
N-tS^-dimethoxyphenyiyNXcis^-l^dimethylamino)^^,?^-
tetrahydroquinazo!in-2-yl]amino}cyclohexyl)thiourea;
N-[4-(dimethylamino)-l-naphthyI]-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cydohexyl)-N'-(2-methoxy-5-methylphenyI)thiourea;
N-(4-bromo-2-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-y]]amino}-
cyclohexyl)-N'-(4-iodophenyl)thiourea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-N'-(2,4,6-tribromophenyl)thiourea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-N'-(2,4,6-trichlorophenyl)thiourea;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyC1-5hexyI)-N'-mesitylthiourea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-N'-(2,4-dimethylphenyl)thiourea;
N-(2,6-diethylpheny!)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoltn-2-yi]amino}cyclohexyl)thiourea;
N-(4-bromo-2,6-dimethylphenyI)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyC1-5hexyl)thiourea;
N-(4-bromo-2-methylphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yI]amino}cyclohexyl)thiourea;
N-[4-bromo-2-ttrifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethylamino)-5,6,7,f
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea;
N-(4-chioro-2-methylphenyI)-NT-(cis-4-{[4-tdimethylamino)-5,6,7,8-
tetrahydroquinazoiin-2-yI]amino}cyclohexyl)thiourea;

969
N"[4-ch]oro-2-(trifluoromethyI)phenyl]-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)thiourea;
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyI)-N'-(4-fluoro-2-methylphenyl)thiourea;
N-(cis-4-{[4-(dimethyIamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-N'-(4-methoxy-2-methy]phenyl)thiourea;
N-(5-chloro-2,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethyIamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea;
N-(2,4-dibromo-6-fluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazoIin-2-yl]amino}cyclohexyl)thiourea;
N-(2,4-dichloro-6-methyIphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yl]amino}cyclohexyl)thiourea;
N-tcis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyI)-N'-(2-ethoxypheny])thiourea;
N-[4-bromo-2-(trifluoromethoxy)phenyl]-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)thiourea;
N-(4-chloro-2,5-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6,7,8-
tetrahydroquinazolin-2-yI]amino}cyclohexyl)thiourea;and
N-(cis-4-{[4-(dimethylamino)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}-
cyclohexyl)-N'-(2,2-diphenylethyI)thiourea;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
50. The compound according to claim 29 wherein R] is selected from the group consisting of:
(i) C]-8 alkyl, and
C]-8 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkoxy,

970
•C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
"C1-5 alkoxy,
(ii) C2-5 alkenyl,
(iii) carbocyclyl,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
■C1-5 alkyl,
•C1-5 alkyl substituted by halogen, and
•C1-5 alkoxy;
L is Formula (VII);
Y is -C(O)O-;
wherein carbocyclic ary! is phenyl or naphthyl;
carbocyclyl is 9//-fluorenyl or menthyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
51. The compound according to claim 50 wherein R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.

971
52. The compound according to claim 2 wherein Q is Formula (IV); p is 0;
R] is selected from the group consisting of:
(i) C]_g alkyl, and
Ct_8 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•C1-5 alkylcarbonyloxy,
"carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by nitro,
•carbocyclic aryloxy substituted by C[.5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by C1-5 alkyl,
"C1-5 alkoxycarbonyl,
•mono-Ci-s alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylamino,
•mono-Ct.5 alkylamino substituted by cyano,
•mono-C1-5 alkylamino substituted by carbocyclic aryl,
•di-C1-5 alkylamino,
"di-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino substituted by carbocyclic aryl,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by C1-5 alkyl,
•di-carbocyclic arylamino,

972
•di-carbocyclic arylamino substituted by C1-5 alkyl,
•C1-5 alkoxycarbonylamino,
•carbocyclic arylcarbonylamino,
•C 1.5 alkyIthio,
•C1-5 alkylthio substituted by substituent(s) independently selected from
the group consisting of:
••carbocyclic ary!,
••carbocyclic aryl substituted by halogen, and
••carbocyclic aryl substituted by C[.5 alkoxy,
•carbocyclic arylthio,
•heterocyc ly Ithio,
•heterocyclylthio substituted by nitro,
•heterocyclylthio substituted by C1-5 alkyl,
•C3-6 cycloalkyl,
*C3^6 cycloalkenyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C1-5 alkyl,
"C1-5 alkoxy,
••C2-5 alkenyl, and
••C2-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulfinyl,
•carbocyclic aryl,

973
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
••hydroxy,
••nitro,
"C1-5 alkyl,
■•C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
***oxo,
•••carbocyclic aryl, and
•••heterocyclyl,
•*C2o aikenyl,
"•C1-5 alkoxy,
••C1-5 alkoxy substituted by halogen,
"C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryloxy,
••carbocyclic aryl, and
••heterocyclyl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
"C1-5 alkyl,
••C1-5 alkyl substituted by carbocyclic aryl,
••C1-5 alkoxy,
"C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryl, and
••carbocyclic aryl substituted by halogen,
(ii) C2-7 aikenyl, and

974
C2-7 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
••C]o alkoxy,
(iii) C2-5 alkynyl, and
C2-5 alkynyl substituted by carbocyclic aryl,
(iv) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:
•C1-5 alky],
•C1-5 atkyl substituted by oxo,
•C1-5 alky! substituted by carbocyclic aryl, and
•carbocyclic aryl,
(v) carbocyclyl,
(vi) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
•C,-5 alky!,
•Cjo alkyl substituted by substituent(s) independently selected from the
group consisting of:

975
"halogen,
••oxo,
••carbocyclic aryloxy,
••carbocyclic aryl, and
••carbocyclic aryl substituted by Cj.5 alkyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••carbocyclic aryl, and
••halogenated carbocyclic aryl,
•C2-5 alkenyloxy,
•C3-6 cycloalkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•C1-5 alkoxycarbonyl,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•amino,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-C1-5 aikylamino substituted by cyano,
•di-C1-5 alkylamino substituted by cyano,
•C2-5 alkynylcarbonylamino,
•C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,
•{carbocyclic aryl)NHC(O)NH,

976
•(carbocyclic aryl)NHC(O)NH substituted by C1-5 alkoxy,
•(carbocyclic aryl)NHC(O)NH substituted by haloganated C1-5 alkoxy,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by halogen,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by cyano,
•mono-C]-5 alkylaminosulfonyl,
•di-C1-5 alkylaminosulfonyl,
•carbocyclic aryl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5 alkyl,
••carbocyclic aryl, and
••halogenated carbocyclic aryl,
(vii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
•C1-5 alky] substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••hydroxy,
••C1-5 alkylthio,
••C1-5 alkylthio substituted by carbocyclic aryl,
"Q_5 alkylthio substituted by halogenated carbocyclic aryl,

977
••carbocyclic aryl,
••carbocyclic aryl substituted by halogen, and
••heterocyclyl,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C].$ alkyl,
•C1-5 alkylthio,
•C2.5 alkenylthio,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by Cu alkoxycarbonyl,
•C1-5 alkylsulfonyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by C1-5 alkyl,
•C1-5 alkoxycarbonyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,
"C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
•heterocyclyl;
wherein carbocyclic aryl is phenyl, naphthyl, or anthranyl;
carbocyclyl is 1,2,3,4-tetrahydronaphthyI, 1-oxo-indanyl, 9-fluorenyl, 9-
oxo-9//-fluorenyl, bicyclo[2.2.1]heptyl, indenyl, or menthyl;
heterocyclyl is 1,2,3-triazolyl, l//-indolyl, 1/f-pyrrolyl, 2,3-dihydro-l-
oxo-isoindolyl, 2,3-dihydro-benzo[l,4]dioxinyl, 2,3-dihydro-benzofuryl, 2,4-
dihydro-3-oxo-pyrazolyl, 2//-benzopyranyl, 2-oxo-benzopyranyl, 3,4-dihydro-2//-

978
benzo[b][l,4]dioxepinyl, 4-oxo-l,5,6,7-tetrahydro-indoIyl, 4-oxo-benzopyranyl,
9//-carbazolyi, 9#-xanthenyl, benzo[l,3]dioxolyl, benzo[2,l,3]oxadiazolyi,
benzo[l,2,5]oxadiazolyl, benzo[b]thienyl, benzofuryl, benzothiazolyl, furyl,
imidazo[2,l-b]thiazolyl, imidazolyl, isoxazolyl, morpholino, pyrazolyl, pyridyl,
pyrimidyl, quinolyl, quinoxalyl, thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pbarmaceutically acceptable salt, hydrate, or solvate thereof.
53. The compound according to claim 52 wherein Ri is selected from the group consisting of:
(i) C]_7 alkyl, and
Ci_7 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•mono-C1-5 alkylamino,
•mono-Cij alkylamino substituted by substituent(s) independently selected
from the group consisting of:
••cyano, and
••carbocyclic aryl,
•di-Cjo alkylamino,
•di-C1-5 alkylamino substituted by substituent(s) independently selected
from the group consisting of:
••cyano, and
••carbocyclic aryl,
•mono-carbocyclic arylamino,
•di-carbocyclic arylamino,

979
•mono-carbocyclic arylamino substituted by C1-5 alkyl,
•di-carbocyclic arylamino substituted by C1-5 alkyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
"C1-5 alkoxy,
(ii) C2-7 alkenyl, and
C2-7 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by C1-5 alkoxy,
(iii) C2-5 alkynyl, and
C2-5 alkynyl substituted by carbocyclic aryl,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•cyano,
•CLS alkyl,
•C1-5 alkyl substituted by halogen,
•Cj.g alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••carbocyclic aryl, and

980
••carbocyclic aryl substituted by halogen,
•C2-5 alkenyloxy,
•mono-C1-5 alkylamino,
•di-Cj.5 alkylamino,
•mono-C1-5 alkylamino substituted by cyano,
•di-C1-5 alkylamino substituted by cyano,
•C1-5 alkylthio, and
•C1-5 alkylthio substituted by halogen,
(v) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkyl,
•Ci.s alkyl substituted by hydroxy,
•C1-5 alkoxy,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by C1-5 alkoxycarbonyl,
"C1-5 alkoxycarbonyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
"C1-5 alkyl substituted by halogen;
L is Formula (VII);
Y is a single bond or -CH2-;
wherein carbocyclic aryl is phenyl or naphthyl;

981
heterocyclyl is l//-indolyl, l//-pyrrolyl, 2,3-dihydro-benzo[l,4]dioxinyl,
4-oxo-benzopyranyl, 9//-carbazolyl, benzo[l,3]dioxolyl, benzo[b]thienyl, furyl,
imidazo[2,l-b]thiazolyl, pyrazolyl, pyridyl, orthienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
54. The compound according to claim 53 wherein Ki is methylamino, or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
55. The compound according to claim 54 wherein Ri is selected from the group consisting of:
(i) C2-5 alkenyl, and
C2-5 alkenyl substituted by carbocyclic aryl.,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•C[.5 alkyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••carbocyclic ary), and
••carbocyclic aryl substituted by halogen,
•C2-5 alkenyloxy,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,

982
•mono-C1-5 alkylamino substituted by cyano, and
•di-C1-5 alkylamino substituted by cyano,
(iii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkyl,
•C1-5 alkoxy,
•C1-5 alkoxycarbonyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••Ci_3 alkyl, and
•*C1-5 alkyl substituted by halogen;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is l//-indolyl, 9//-carbazolyI, benzo[l,3]dioxolyl, pyrazolyl,
or pyridyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
56. The compound according to claim 55 wherein Ri is selected from the group consisting of:
(i) C2-5 alkenyl, and
C2-5 alkenyl substituted by carbocyclic aryl,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,

983
•hydroxy,
•C1-5 alkyl,
"C1-5 alkoxy,
•C1-5 alkoxy substituted by halogen,
•C2-5 alkenyloxy,
(iii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkyl,
•C1-5 alkoxy,
"C1-5 alkoxycarbonyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by C1-5 alkyl, and
•carbocyclic aryl substituted by halogenated C1-5 alkyl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is I/f-indolyl, 9/f-carbazolyl, benzo[l,3]dioxolyl, or
pyrazolyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
57. The compound according to claim 1 selected from the group consisting of:
N2-(cis-4-{[(5-bromo-lH-indol-3-yI)methyl]amino}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-[cis-4-({[5-(4-fluoropheny!)pyridin-3-yl]methyI}amino)cyclohexyl]-N4,N4-
dimethylpyrimidine-2,4-diamine;
ethyl 4,6-dichloro-3-{ [(cis-4-{ [4-(dimethyIamino)pyrimidin-2-yl]amino}-
cyclohexyl)amino]methyl}-lH-indole-2-carboxylate;

984
N"-(cis-4-{[(2,6-dimethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4- {[(2-ethoxybenzyl)amino]methyl} cyc!ohexyI)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-[cis-4-({[(4-methoxy-l-naphthyl)methyl]amino}methyI)cyclohexyl]-N4,N4-
dimethyIpyrimidine-2,4-diamine;
N2-[cis-4-({[(5-methoxy-lH-indol-3-yl)methyI]amino}methyI)cyclohexyI]-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-[cis-4-({[(2-methoxy-l-naphthyI)methyl]amino}methy))cyclohexy]]-N4,N4-
dimethyIpyrimidine-2,4-diamine;
4-bromo-2-( {[(cis-4-{ [4-(dimethylamino)pyrimidin-2-yl]amino} -
cydohexyI)methyl]amino}methyl)-6-methoxyphenol;
N2-[cis-4-({[(5-bromo-lH-indol-3-yl)methyl]amino}methyI)cyclohexyl]-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(2,4-dimethoxybenzy])amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,3,4-trimethoxybenzyl)amino]methyl}-
cyclohexyl)pyrimidine-2,4-diamine;
N2-(cis-4-{[(3-ethoxy-4-methoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethyIpyrimidine-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[f{3-[4-(trifluoromethyl)phenyl]-lH-pyrazol-4-
yI}methyI)amino]methyl}cyclohexyl)pyrimidine-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(3,4,5-trimethoxybenzyl)amino]methyl}-
cyclohexyI)pyrimidine-2,4-diamine;
4-({[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyI)-
methyl]amino}methyl)-2-iodo-6-methoxyphenol;
4-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)methyI]-
amino}methyl)-2>6-dimethylphenoI;

985
N2-(cis-4-{[(5-bromo-2,4-dimethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N"-(cis-4-{[(5-bromo-2-methoxybenzyl)amino]methyl}cyclohexyI)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-[cis-4-({[4-(diethylamino)benzyl]amino}methyl)cyclohexyl]-N4,N4-
dimethyIpyrimidine-2,4-diamine;
N2-[cis-4-({[t9-ethyl-9H-carbazol-3-yl)methyl]amino}methyl)cyclohexyl]-N4,N4
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(4-isopropoxybenzyl)amino]methyI}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4- {[(3,3-diphenyIprop-2-en-1 -yl)amino]methy 1} cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
4-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)methyl]-
amino}methyl)-2-ethoxyphenol;
N2-{cis-4-[({[4-(dimethylamino)-l-naphthyl]methyl}amino)methyl]-cyclohexyl}
N4,N4-dimethylpyrimidine-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,6-trimethoxybenzyl)amino]methyl}-
cyclohexyl)pyrimidine-2,4-diamine;
N2-tcis-4-{[(5-bromo-2-ethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethy!pyrimidine-2,4-diamine;
N2-(cis-4-{[(2,4-dimethoxy-3-methylbenzyl)amino]methyl}cyC1-5hexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[t2,5-diethoxybenzyl)amino]methy]}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(2,4-diethoxybenzyI)amino]methyI}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N"-(cis-4-{[(3,5-dibromo-2-methoxybenzyl)amino]methyl}cyclohexyI)-N4,N4-
dimethylpyrimidine-2,4-diamine;

986
N4,N4-dimethy]-N2-(cis-4-{[(2,4,5-triethoxybenzyl)amino]methyl}-
cyclohexyl)pyrimidine-2,4-diamine;
N4,N4-dimethyI-N2-(cis-4-{[(2,4,5-trimethoxybenzyl)amino]methyl}-
cyclohexyl)pyrimidine-2,4-diamine;
N2-[cis-4-({[2-(allyIoxy)benzyl]amino}methyl)cyclohexyl]-N4,N4-
dimethylpyrimidine-2,4-diamine;
N4,N4-dimethyl-N2-[cis-4-({[(l-methyl-lH-indol-3-yl)methyl]amino}-
methyl)cyclohexyl]pyrimidine-2,4-diamine;
N"-[cis-4-({[(7-methoxy-l,3-t>enzodioxol-5-yl)methyl]amino}methyl)-
cyC1-5hexy!]-N4,N4-dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(3-bromo-4,5-dimethoxybenzyl)amino]methyI}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N"-(cis-4-{[(4-methoxy-3-methylbenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethyIpyrimidine-2,4-diamine;
N2-(cis-4- {[(2-bromo-4,5-dimethoxybenzy l)amino]methyl} cyclohexy 1)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N"-(cis-4-{[(3?4-dimethoxybenzyI)amino]methyl}cyclohexyl)-N4,N -
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(4-methoxy-2,5-dimethyIbenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethyIpyrimidine-2,4-diamine;
3-[[4-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-
methyl]amino}methyl)phenyl](methyl)amino]propanenitrile;
N2-{cis-4-[({4-[(4-bromobenzyl)oxy]benzyl}amino)methyl]cyclohexyl}-N4,N4-
dimethylpyrimidine-2r4-diamine;
N2-(cis-4-{[(3,5-dibromo-2-ethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-[4-(4-bromo-2-trifluoromethoxy-benzyl)amino-cyclohexyl]-N4,N4-dimethyl-
pyrimidine-2,4-diamine;

987
N2-{cis-4-[2-(4-bromo-2-trifluoromethoxy-phenyl)-ethylamino]-cyclohexyl}-
N ,N -dimethyl-pyrimidine-2,4-diamine; and
N2-{cis-4-[(4-bromo-2-trifluoromethoxy-benzyl)amino-methyl]-cyclohexyl}-
N4,N4-dimethyl-pyrimidine-2,4-diamine;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
58. The compound according to claim 57 selected from the group consisting of:
ethyl 4,6-dichIoro-3-{[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)amino]methyl}-lH-indole-2-carboxylate;
N2-[cis-4-( {[(4-methoxy-1 -naphthyl)methyl]amino} methyl)cyclohexyl]-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-[cis-4-({[(2-methoxy-l-naphthyl)methyl]amino}methyl)cyclohexyl]-N4,N4-
dimethylpyrimidine-2.4-diamine;
4-bromo-2-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)methyI]amino}methyl)-6-methoxyphenol;
N2-[cis-4-({[(5-bromo-lH-indol-3-yl)methyl]amino}methyl)cyclohexyl]-N4,N4'
dimethylpyrimtdine-2,4-diamine;
N4,N4-dimethyI-N2-(cis-4-{[(2,3,4-trimethoxybenzyl)amino]methyl}-
cyclohexyI)pyrimidine-2,4-diamine;
N2-(cis-4-{[(3-ethoxy-4-methoxybenzyl)amino]methy]}cyC1-5hexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[({3-[4-(trifluoromethyl)phenyl]-lH-pyrazol-4-
yl}methyl)amino]methyl}cyclohexyl)pyrimidine-2,4-diamine;
4-({[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-
amino}methyl)-2-iodo-6-methoxyphenol;
4-({[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-
amino}methyl)-2;6-dimethylphenoI;

988
N~-(cis-4-{[(5-bromo-2,4-dimethoxybenzyI)amino]methyI}cyclohexyi)-N4,N4-
dimethy!pyrimidine-2,4-diamine;
N"-(cis-4-{[(5-bromo-2-methoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethyipyrimidine-2,4-diamine;
N2-[cis-4-({[(9-ethy]-9H-carbazol-3-yl)methyl]amino}methyI)cyclohexyI]-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(3,3-diphenylprop-2-en-l-yl)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,6-trimethoxybenzyl)amino]methyI}-
cyC1-5hexyl)pyrimidine-2,4-diamine;
N2-(cis-4-{[(5-bromo-2-ethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-tcis-4-{[(2,4-dimethoxy-3-methylbenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-(cis-4-{[(2,5-diethoxybenzyl)amino]methyl}cyclohexyl)-N4,N4'
dimethyIpyrimidine-2,4-diamine;
N2-(cis-4-{[t3,5-dibromo-2-methoxybenzyl)amino]methyl}cyclohexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N4,N4-dimethyl-N2-(cis-4-{[(2,4,5-triethoxybenzyl)amino]methyl}'
cyclohexyl)pyrimidine~2,4-diamine;
N2-[cis-4-({[2-(allyloxy)benzyl]amino}methyl)cyclohexyl]-N4,N4-
dimethylpyrimidine-2,4-diamine;
N"-[cis~4-({[(7-methoxy-l,3-benzodioxol-5-yl)methyl]amino}methyl)-
cyclohexyl]-N4,N4-dimethylpyrimtdine-2,4-diamine;
N2-(cis-4-{[(3-bromo-4,5-dimethoxybenzyl)amino]methyl}cyC1-5hexyl)-N4,N4-
dimethylpyrimidine-2,4-diamine;
N2-{cis-4-[2-(4-bromo-2-trifluoromethoxy-phenyl)-ethylamino]-cyclohexyl}-
N4,N4-dimethyl-pyrimidine-2,4-diamine; and

989
N"-{cis-4-[(4-bromo-2-trifluoromethoxy-benzyl)amino-methyl]-cyC1-5hexyl}-
N ,N -dimethyl-pyrimidine-2,4-diamine;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
59. The compound according to claim 52 wherein R\ is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•oxo,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•C1-5 alkylcarbonyloxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by nitro,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
• heterocy c ly loxy,
•heterocyclyloxy substituted by C1-5 alkyl,
•mono-C1-5 alkyl am inocarbonyl,
•di-C|.5 alky lam inocarbonyl,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-carbocyclic arylamino,
•di-carbocyctic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•di-carbocyclic arylamino substituted by halogen,
•carbocyclic arylcarbonylamino,
•C1-5 alkoxycarbonylamino,

990
•C1-5 alkylthio,
•C1-5 alkylthio substituted by substituent(s) independently selected from
the group consisting of:
••carbocyclic aryl, and
••carbocyclic aryl substituted by substituent(s) independently
selected from the group consisting of:
•••halogen, and
"•C1-5 alkoxy,
•carbocyclic arylthio,
•heterocyclylthio,
•heterocyclylthio substituted by C1-5 alkyl,
•heterocyclylthio substituted by nitro,
"C3-6 cycloalkyl,
•C3-6 cycloalkenyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C.5 alkyl,
••C1-5 alkoxy,
••C2-5 alkenyl, and
••C2-5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulfinyl,
•carbocyclic aryi,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:

991
••halogen,
••hydroxy,
••nitro,
"C1-5 alkyl,
••C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••oxo,
"•carbocyclic aryl, and
•••heterocyclyl,
"C1-5 alkoxy,
"C1-5 alkoxy substituted by halogen,
"C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryloxy,
••carbocyclic aryl, and
••heterocyclyl,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••Cu alkyl,
••C1-5 alkyl substituted by carbocyclic aryl,
••C1-5 alkoxy,
"C1-5 alkoxy substituted by carbocyclic aryl,
••carbocyclic aryl, and
"•carbocyclic aryl substituted by halogen,
(ii) C2-5 alkenyl, and
C2-5 alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,

992
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
••nitro,
(iii) C3-6 cycloalkyl, and
C3-6 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••oxo, and
••carbocyclic aryl, and
•carbocyclic aryl,
(iv) carbocyclyl,
(v) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•cyano,
•nitro,
•d.5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••oxo,
••carbocyclic aryloxy,
••carbocyclic aryl, and

993
••carbocyclic aryl substituted by C1-5 alkyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-C1-5 alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-Ci_s alkylaminocarbonyl substituted by carbocyclic aryl,
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•ami no,
•mono-C1-5 alkylamino,
•di-C1-5alkylamino,
•C2.5 alkynylcarbonylamino,
•C2-5 alkynylcarbonylamino substituted by carbocyclic aryl,
•(carbocyclic aryl)NHC(O)NH,
•(carbocyclic aryI)NHC(O)NH substituted by C1-5 alkoxy,
•(carbocyclic aryI)NHC(O)NH substituted by haloganated C1-5 alkoxy,
•C1-5 alkylthio,
•C1-5 alkylthio substituted by halogen,
•carbocyclic arylthio,
•carbocyclic arylthio substituted by cyano,
•mono-C1-5 alkylaminosulfonyl,
•di-C1-5 alkylaminosulfonyl, and
•carbocyclic aryl,
•carbocyclic aryl substituted by halogen,

994
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5 alkyl,
••carbocyclic aryl, and
••halogenated carbocyclic aryl,
(vi) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C,_5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••C1-5 alkylthio,
•*C1-5 alkylthio substituted by carbocyclic aryl,
"C1-5 alkylthio substituted by halogenated carbocyclic aryl,
••carbocyclic aryl,
••carbocyclic aryl substituted by halogen, and
••heterocyclyl,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C1-5 alkyl,
•C1-5 alkylthio,
•C2-5 alkenylthio,
•carbocyclic arylthio,

995
•C1-5 alkylsulfonyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by C1-5 alkyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
••C,_5 alkyl,
•heterocyclyl;
L is Formula (VII);
Y is -C(O)-;
wherein carbocyclic aryl is phenyl, naphthyl, or anthranyl;
carbocyclyl is 1,2,3,4-tetrahydronaphthyl, 1-oxo-indanyl, 9-oxo-9H-
fluorenyl, or indenyl;
heterocyclyl is 1,2,3-triazolyl, lif-indolyl, l//-pyrrolyl, 2,3-dihydro-l-
oxo-isoindolyl, 2,3-dihydro-benzofuryl, 2,4-dihydro-3-oxo-pyrazolyl, 2H-
benzopyranyl, 2-oxo-benzopyranyl, 4-oxo-l,5,6,7-tetrahydro-indoIyl, 9H-
xanthenyl, benzo[l,3]dioxolyl, benzo[2,l,3]oxadiazolyl, benzo[l,2,5]oxadiazolyl,
benzo[b]thienyl, benzofuryl, benzothiazolyl, furyl, imidazolyl, isoxazolyi,
morpholino, pyrazolyl, pyridyl, pyrimidyl, quinolyl, quinoxalyl, thiazolyl, or
thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
60. The compound according to claim 59 wherein R2 is hydrogen, trifluoromethyl, methoxy,
methylamino, dimethylamino, ethylamino, ethylm ethyl ami no, or

996
hydroxylethylmethylamino; p is 0; R3 and R4 are hydrogen; A is a single bond; B is a single
bond or -CH2-;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
61. The compound according to claim 60 wherein Ri is selected from the group consisting of:
(i) C1-5 alky], and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•oxo,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-Ci-s alkylaminocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-carbocyclic arylamino,
*di-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•di-carbocyclic arylamino substituted by halogen,
•carbocyclic arylcarbonylamino,
•C,_5 alkylthio,
•C3-6 cycloalkyl,
•carbocyclyl,
•carbocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
-C1-5 alkyl,

997
••C2-5 alkenyl, and
••C2_5 alkenyl substituted by substituent(s) independently selected
from the group consisting of:
•••carbocyclic aryl, and
•••carbocyclic aryl substituted by C1-5 alkylsulfinyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
•'nitre,
••Ct_5 alkyl,
"C1-5 alkyl substituted by substituent(s) independently selected
from the group consisting of:
•••oxo,
•••carbocyclic aryl, and
•••heterocyclyl,
••Ct_5 alkoxy,
"C1-5 alkoxy substituted by halogen,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
-C1-5 alkyl,
••carbocyclic aryl, and
••carbocyclic aryl substituted by halogen,
(ii) C2-5 alkenyl, and
C2o alkenyl substituted by substituent(s) independently selected from the
group consisting of:

998
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
••nitro,
(iii) carbocyclyl,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,
•nitro,
•Ci-s alkyl,
•C1-5 alky] substituted by substituent(s) independently selected from the
group consisting of:
••halogen,
••oxo, and
••carbocyclic aryl,
•C1-5 alkoxy,
*C1-5 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
•'carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C|_5 alkoxy,
•mono-C1-5 alkylaminocarbonyl,
•di-C[-5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,

999
•di-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•mono-Ci_g alkylamino,
•di-C1-5 alkylamino,
•C2-5 alkynylcarbonylamino,
•C2.5 alkynylcarbonylamino substituted by carbocyclic aryl,
•mono-Ci_g alkylaminosulfonyl, and
•di-C1-5 alkylaminosulfonyl,
(v) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5 alkylthio,
"C[.5 alkylthio substituted by carbocyclic aryl,
••C1-5 alkylthio substituted by halogenated carbocyclic aryl,
••carbocyclic aryl,
••carbocyclic aryl substituted by halogen, and
••heterocyclyl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C,.s alkyl,
•C1-5 alkylthio,
•Ci-g alkylsulfonyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by C1-5 alkyl,

1000
•carbocyclicaryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
"C1-5 alkyl,
•heterocyclyl;
wherein carbocyclic aryl is phenyl or naphthyl;
carbocycly] is 1-oxo-indanyl, 9-oxo-9//-fluorenyl, or indenyl;
heterocyclyl is 1,2,3-triazolyI, l//-indolyl, l//-pyrrolyl, 2,3-dihydro-
benzofuryl, 2//-benzopyranyI, 9//-xanthenyl, benzo[2,l,3]oxadiazolyl,
benzo[l,2,5]oxadiazolyl, benzo[b]thienyl, furyl, isoxazolyl, morpholino, pyrazolyl,
pyridyl, quinoiyl, quinoxalyl, thiazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
62. The compound according to claim 61 wherein Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•oxo,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino,
•mono-carbocyciic arylamino,
•di-carbocyclic arylamino,

1001
•mono-carbocyclic arylamino substituted by halogen,
•di-carbocyclic arylamino substituted by halogen,
•C1-5 alkylthio,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••hydroxy,
"C1-5 alkyl,
••C1-5 alkoxy, and
••C1-5 alkoxy substituted by halogen,
•heterocyclyl, and
•heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5 alkyl,
"carbocyclic aryl, and
••carbocyclic aryl substituted by halogen,
(ii) C2-5 alkenyl, and
C2o alkenyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by nitro,
(iii) carbocyclyl,
(iv) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•hydroxy,

1002
"nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy,
•Cj.5 alkoxy substituted by halogen,
■C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by C1-5 alkoxy,
*mono-C1-5 alkyl am inocarbonyl,
•di-C1-5 alkylaminocarbonyl,
•mono-C1-5 alkylaminocarbonyl substituted by carbocyclic aryl,
•di-Cj.s alkylaminocarbonyl substituted by carbocyclic aryl,
•mono-C1-5 alkylaminosulfonyl, and
•di-C1-5 alkylaminosulfonyl,
(v) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
••C1-5 alkylthio,
••Cj.5 alkylthio substituted by carbocyclic aryl, and
••C1-5 alkylthio substituted by halogenated carbocyclic aryl,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by halogen,
•carbocyclic aryloxy substituted by d_5 alkyl,

1003
•carbocyclic aryl,
•carbocyclic aryl substituted by halogen,
•carbocyclic aryl substituted by nitro, and
•heterocyclyl;
wherein carbocyclic aryl is phenyl or naphthyl;
carbocyclyl is 1-oxo-indanyl;
heterocyclyl is 1,2,3-triazolyl, l//-indolyl, l#-pyrrolyl, 2,3-dthydro-
benzofuryl, 9//-xanthenyl, benzo[2,l,3]oxadiazolyl, benzo[l,2,5]oxadiazolyl,
benzo[b]thienyl, furyl, isoxazolyl, pyridyl, quinoxalyl, thiazolyl, orthienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
63. The compound according to claim 1 selected from the group consisting of:
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-
methoxybenzamide;
3-bromo-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-2,l,3-
benzoxadiazoIe-5-carboxamtde;
3-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
4-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
4-chloro-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-3-
nitrobenzamide;
3,5-dichloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)benzamide;

1004
3,4-dichloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-2,2-
diphenylacetamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3,4-
difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-3,5-
difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-fluoro-5-
(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-4-methyl-3-
nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-3-
nitrobenzamide;
N-tcis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-
phenoxybutanamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethoxy)benzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-3-
methylbenzaraide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-3-
iodobenzamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyclohexy!)-2,5-dimethyl-3-
furamide;
3-chloro-N-(cis-4-{[4-(dimethyiamino)pyrimidin-2-yl]amino}cyclohexyl)-4-
fluorobenzamide;

1005
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-3,5-
d i m eth oxyben zam i de;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3,5-
bis(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-4-fluoro-3-
methylbenzamide;
2,5-dichloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}-
cyclohexyl)thiophene-3-carboxamide;
l-benzyl-3-tert-butyl-N-tcis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)-lH-pyrazole-5-carboxamide;
N-(cis-4- {[4-(dimethy lamino)pyrimidin-2-yl]amino} cydohexyl)-2-( 1 -
naphthy l)acetamide;
2-(4-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)acetamide;
l-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyc loh exy I )cy c lopentanecarboxamide;
3-(2-chloro-6-fluorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyI)-5-methylisoxazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-4-fluoro-3-
(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-5-methyl-2-
phenyl-2H-l,2,3-triazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(4-
methoxyphenoxy)-5-nitrobenzamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyclohexyI)-2-
phenoxyacetamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-quinoxaIine-2-
carboxamide;

1006
N-(cis-4-{[4-(dimethy]amino)pyriraidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-2-
(pentafluorophenoxy)acetamide;
2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino} cyclohexyl)acetaraide;
3-(2,6-dichIorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)-5-methylisoxazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-2-
phenoxynicotinamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(4-
methylphenoxy)nicotinamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-4-
[(dipropylamino)sulfonyl]benzamide;
2-(4-chlorophenoxy)-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)-2-methylpropanamide;
2-(2,3-dihydro-I-benzofuran-5-yl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yI]amino}cyclohexyl)-l,3-thiazole-4-carboxamide;
3-tert-butyI-l-(2,4-dichlorobenzyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyc!ohexyI)-IH-pyrazole-5-carboxamide;
6-chloro-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-2H-
chromene-3-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(2-thienyl)-l,3-
th iazoIe-4-c arboxam tde;
5-(4-chloro-2-nitrophenyI)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)-2-furamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-5-iodo-2-
furamide;

1007
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-5-(4-methyI-2-
nitropheny])-2-furamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-5-nitrothiophene-
2-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-3-methyI-4-
nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-methoxy-4-
nitrobenzamide;
1 -benzyl-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-y3]amino} cyclohexy I)-1H-
indoIe-3 -carboxamide;
3-acetyI-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-
benzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-2-
furamide;
5-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)-2-furamide;
4,5-dibrotno-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}-
cy c loh exy l)th iophene-2-c arboxamide;
2-(3,5-di-tert-butyI-4-hydroxyphenyl)-N-(cis-4-{[4-(dimethyIamino)-pyrimidin-2-
y 1] am ino} cy clohexy I)acetamide;
N2,N6-dibenzoyl-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}-
cyclohexyl)lysinamide;
3-(dimethylamino)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)benzamide;
4,5-dibromo-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}-cyclohexyl)-2-
furamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(IH-indol-3-
yl)acetamide;

1008
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(5-methyl-2-
phenyl-l,3-thiazol-4-yl)acetamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(lH-indol-3-
yl)-4-oxo-4-phenylbutanamide;
4-(4-bromophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)-2~(lH-indol-3-yl)-4-oxobutanamide;
3,5-dichloro-N-(cis-4~{[4-(dimethylatnino)pyrimidin-2-yl]amino}-cyclohexyl)-2-
[(3-phenylprop-2-ynoyl)amino]benzamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-2-(l-methyl-1H-
indol-3-yl)-4-(4-methylphenyl)-4-oxobutanamide;
N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexyl)-2-methyl-1 -(3-
morpholin-4-ylpropyl)-5-phenyl-lH-pyrrole-3-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-4-(4-
nitrophenyl)butanamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(2-phenyl-lH-
indol-3-yl)acetamide;
N2-benzoyl-N -(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)-
N^N'-dipropylglutamamide;
N-(ciS"4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-
phenoxybenzamide;
3-benzoyl-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}-
cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-2-(ethylthio)-2,2-
diphenylacetamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-Nr-[(lR)-l-(l-
naphthy l)ethy 1 ] phth al am i de;
(2S)-2-(3-benzoyIphenyl)-N-(cis-4-{[4-{dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)propanamide;

1009
N'-(cis-4- {[4-(dimethy lamino)pyrimidin-2-y l]amino} cyclohexyl)-N,N-bis[( 1S)-1 -
phenylethyl]phthalamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-2-{(lE)-5-fluoro-
2-methyl-l-[4-(methylsulfinyl)benzylidene]-lH-inden-3-yl}acetamide;
N-(cis-4-{[4-tdimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyI)-2-[4-(2-
thienylcarbonyi)phenyl]propanamide;
3-(benzyloxy)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)-
4-methoxybenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-methyl-l,5-
dipheny I-1 H-pyrroIe-3-carboxamide;
l-{2-[(2-chloro-6-fluoroben2yl)thio]ethyl}-N-(cis-4-{[4-(dimethylamino)-
pyrimidin-2-yl]amino}cyclohexyI)-2-methyl-5-phenyl-lH-pyrrole-3-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-
phenoxyben2amide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-
phenylquinoIine-4-carboxamide;
2-[4-(4-chlorophenyl)-2-phenyl-l,3-thiazol-5-yl]-N-(cis-4-{[4-
(dimethyiamino)pyrimidin-2-yl]amino}cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-l-[(4-
methylpbenyl)sulfonyl]-lH-pyrroIe-3-carboxamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-5-(3-
nitrophenyl)-2-furamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-4-
(isopropy!suIfonyl)-5-(methylthio)thiophene-2-carboxamide;
N-(cis-4-{[4-(dimethy!amino)pyrimidin-2-yI]amino}cyclohexyl)-3-iodo-4-
(isopropylsulfonyl)-5-(methyIthio)thiophene-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-5-nitrothiophene-
3-carboxamide;

1010
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-l-methyl-4-nitro-
1 H-pyrrole-2-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-4-
nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3,5-dimethyl-4-
nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]arnino}cyclohexyl)-2-mesityl-2-
oxoacetamide;
3,5-di-tert-butyl-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)-
4-hydroxybenzamide;
4-chIoro-N-[{cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyclohexyI)-
methyljbenzamide;
(2E)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-methyl]-3-
ph enyl aery lam ide;
4-cbIoro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
methyl]-3-nitrobenzamide;
2-(4-chlorophenyl)-N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-yI]amino} -
cyclohexyl)methyl]acetamide;
3,5-dichloro-N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}-
cyclohexyl)methyl]benzamide;
3,4-dichloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cy c lohexy l)methy l]benzam ide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)methyl]-2,2-
diphenylacetamide;
2,4-dichloro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyI)methyl]-5-fIuorobenzamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-
phenoxybutanamide;

1011
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-
phenylbutan amide;
N-[(cis-4-{[4-(dimethylatnino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-(3-
methoxyphenyl)acetamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-(4-
methoxypheny l)ac etam i d e;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyi]-3,5-
bis(trifluoromethyl)benzamide;
(2E)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-methyl]-3-
(4-nitrophenyI)acrylamide;
2-(2-bromophenyl)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)methyl]acetamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-
(propylthio)nicotinamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-(l-
naphthyl)acetamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-9-oxo-
9H-fluorene-4-carboxamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2,4!6-
trimethy lbenzamide;
2,4,6-trichIoro-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)methyl]benzamide;
(2E)-3-(2-chlorophenyI)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methy!]acrylamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-(2,3,6-
trichlorophenyl)acetamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2,3-
diphenylpropanamide;

1012
N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyl)methyl]-5-iodo-
2-furamide;
(2E)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-methyI]-3-
(3-nitrophenyI)acryIamide;
N-[(cis-4-{[4-(dtmethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)methyl]-3-
oxoindane-1 -carboxamide;
2-benzyl-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-
methyljbenzamide;
2,2-bis(4-chlorophenyl)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]acetamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-3-
methy 1-4-nitrobenzam ide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexy))methyl]-3-
methoxy-4-n itrobenzam ide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2-[2-
(trifluoromethoxy)phenyl]acetamide;
N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexyl)methy 1]-9H-
xanthene-9-carboxamide;
2-(l-benzothien-3-yI)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]acetamide;
N-[cis-4-(4-dimethylamino-pyrimidin-2-yIamino)-cyclohexyl]-2-(4-fluoro-
phenoxy)-nicotinamide;
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyC1-5hexyl]-C-(ethyl-phenyl-
amino)-acetamide;
C-[cis-(4-chloro-phenyl)-ethyI-amino]-N-[4-(4-dimethylamino-pyrimidin-2-
ylamino)-cyclohexyl]-acetamide;
2-(3,4'difluoro-phenyl)-N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-
cyclohexyl]-acetamide;

1013
4-chloro-N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyC1-5hexyI]-3-fluoro-
benzamide;
5-bromo-N-[cis-4-(4-dimethy)amino-pyrimidin-2-ylamino)-cyclohexyl]-
nicotinamide;
3-chloro-4-fluoro-N-[cis-4-(4-methylamino-pyrimidin-2-ylamino)-cyclohexyl]-
benzamide;
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-4-fluoro-
benzamide;
3-chIoro-N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-5-fluoro-
benzamide;
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyC1-5hexyl]-3,4,5-trifIuoro-
benzamide;
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexylmethyl]-3,4-difluoro-
benzamide;
2-(3,4-dichIoro-phenoxy)-N-[cis-4-(4-dimethy!amino-pyrimidin-2-ylamino)-
cyclohexylj-acetamide;
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-2-(3-methoxy-
phenoxy)-acetamide; and
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-C-(ethyl-phenyl-
am ino)-ac etam ide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
64. The compound according to claim 63 selected from the group consisting of:
3-bromo-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)-
benzamide;
N-(cis-4-{ [4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-2,1,3-
ben zoxad i azo 1 e- 5 -carboxam i de;

1014
3-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-
benzamide;
4-chIoro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-
nitrobenzamide;
3,5-dichloro-N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}-
cyclohexyl)benzamide;
3,4-dichloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)-3,4-
difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-
nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethoxy)benzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-
iodobenzamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-4-
fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3,5-
d imethoxy benzami de;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3,5-
bis(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-4-fIuoro-3-
methylbenzamide;
2-(4-ch]orophenoxy)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)acetamide;

1015
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-4-fluoro-3-
(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-5-methyI-2-
phenyl-2H-l,2,3-triazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(4-
methoxyphenoxy)-5-nitrobenzamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)-quinoxaline-2-
carboxamide;
2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyc lohexy 1 )acetam id e;
3-(2,6-dichlorophenyI)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyC1-5hexyl)-5-methylisoxazole-4-carboxamide;
N-(cis-4-{[4-(diraethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(4-
methylphenoxy)nicotinamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-4-
[(dipropylamino)sulfonyl]benzamide;
2-(2,3-dihydro-1 -benzofuran-5-yI)-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-
yl]amino} cyclohexyl)-1,3-thiazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-2-(2-thienyl)-l,3-
th iazole-4-carboxam i de;
5-(4-chIoro-2-nitrophenyl)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)-2-furamide;
N-(cis-4~{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-3-methoxy-4-
nitrobenzamide;
5-bromo-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexyl)-2-
furamide;
5-(4-chloropheny l)-N-(cis-4- {[4-(dimethylamino)pyrimidin-2-y l]amino} -
cyclohexyl)-2-furamide;

1016
2-(3,5-di-tert-butyl-4-hydroxyphenyl)-N-(cis-4-{[4-(dimethylamino)-pyrimidin-2-
yl]amino}cyclohexyl)acetamide;
4,5-dibromo-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)-2-
furamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(lH-indoI-3-
yl)-4-oxo-4-phenylbutanamide;
N-(cis-4-{ [4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexyl)-2-( 1 -methyl-1H-
indol-3-yl)-4-(4-methylphenyl)-4-oxobutanamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(2-phenyl-lH-
indol-3 -y l)acetam ide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-(ethylthio)-2,2-
diphenylacetamide;
N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-N,N-bis[(lS)-l-
phenylethyl]phthalamide;
3-(benzyloxy)-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)-
4-methoxybenzamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-2-methyl-l,5-
dipheny 1-1 H-pyrroIe-3-carboxamide;
l-{2-[(2-chloro-6-fluorobenzyt)thio]ethyI}-N-(cis-4-{[4-(dimethylamino)-
pyrimidin-2-yl]amino}cyclohexyl)-2-methyI-5-phenyl-lH-pyrrole-3-carboxamide;
2-[4-(4-chIorophenyl)-2-phenyl-l,3-thiazol-5-yl]-N-(cis-4-{[4-
(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-5-nitrothiophene-
3-carboxamide;
N-(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyclohexyl)-l-methyl-4-nitro-
lH-pyrrole-2-carboxamide;
3,5-di-tert-butyl-N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-cyclohexyl)-
4-hydroxybenzamide;

1017
N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-2,2-
diphenylacetamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)methyl]-2-
phenylbutanamide;
(2E)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yi]amino}cyclohexyI)-methyI]-3-
(4-nitrophenyl)acrylamide;
N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} eye lohexyl)m ethyl ]-2-( 1 -
naphthyl)acetamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)methyl]-2-(2,3,6-
trich loropheny 1 )acetamide;
(2E)-N-[{cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-methyl]-3-
(3 -n itropheny l)acry lamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-3-
oxoindane-1-carboxamide;
2,2-bis(4-chlorophenyl)-N-[(cis-4-{[4-(dimethylamino)pyriraidin-2-
yl]amino}cyclohexyl)methyl]acetamide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-3-
methy 1 -4-n itrobenzam i de;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-3-
methoxy-4-n itrobenzam ide;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)methyl]-2-[2-
(trifl uoromethoxy)pheny 1] ac etam i de;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-9H-
xanthene-9-carboxam ide;
2-(l-benzothien-3-yI)-N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]acetamide;
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-2-(4-fluoro-
phenoxy)-nicotinamide;

1018
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexy)]-C-(ethyl-phenyl-
amino)-acetamide;
C-[cis-(4-chloro-phenyI)-ethyl-amino]-N-[4-(4-dimethylamino-pyrimidin-2-
ylamino)-cyclohexyl]-acetamide;
4-chloro-N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-3-fluoro-
benzamide;
N-[cis-4-(4-dimethyIamino-pyrimidin-2-ylamino)-cyclohexyl]-3,4,5-trifluoro-
benzamide;
2-(3,4-dichIoro-phenoxy)-N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-
cyclohexylj-acetamide;
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-2-(3-methoxy-
phenoxy)-acetamide; and
N-[cis-4-(4-dimethylamino-pyrimidin-2-ylamino)-cyclohexyl]-C-(ethyl-phenyl-
amino)-acetamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
65. The compound according to claim 52 wherein Ri is selected from the group consisting of:
(i) C1-5 alky I, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkoxy carbonyl,
•C1-5alkylthio,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
••C2.5 alkenyl,

1019
(ii) C3-6 cycloalkyl,
C3-6 cycloalkyl substituted by carbocyclic aryl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•cyano,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•Cj-5 alkoxy carbonyl,
•C1-5 alkoxy,
•C3-6 cycloalkoxy,
•carbocyclic aryloxy,
•Q_5 alkylthio, and
•carbocyclic ary],
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen, and
•carbocyclic aryl;
L is Formula (VII);
Y is -C(O)NR5-;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is 2,3-dihydro-benzo[l,4]dioxinyl, 3,4-dihydro-2//-
benzo[b][l,4]dioxepinyl, benzo[l,3]dioxolyl, furyl, or isoxazolyl; and
halogen is fluoro, chloro, bromo, or iodo;

1020
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
66. The compound according to claim 65 wherein R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-: Rg is hydrogen;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
67. The compound according to claim 66 wherein Ri is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by carbocyclic aryl,
(ii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•nitro,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy, and
"C3-6 cycloalkoxy,
(iii) heterocyclyl, and
heterocyclyl substituted by C1-5 alkyl, and
heterocyclyl substituted by carbocyclic aryl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is isoxazolyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
68. The compound according to claim 1 selected from the group consisting of:
N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyC1-5hexyl)-N'-mesitylurea;

1021
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)-N'-(2,4,6-
trichlorophenyl)urea;
N-(cis-4-{[4-(dimethyiamino)pyrimidin-2-yl]amino}cyclohexyI)-N'-(2,4,6-
tribromophenyl)urea;
N-t2,4-dibromo-6-fluorophenyI)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
y l]amino} cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-Nh-
(diphenylmethyl)urea;
N-(4-bromo-2,6-dimethylphenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)urea;
N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexy l)-N'-[ 1 -(1 -
naphthy l)ethy I ] urea;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-N'-(3,4,5-
trimethoxyphenyl)urea;
N-(4-chloro-2-methylphenyl)~N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)urea;
N-(5-chloro-2,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-pyrimidin-2-
yl]amino} cyclohexyl)urea;
N-(4-bromo-2-methylphenyI)-N'-(cis-4-{[4-tdimethyIamino)pyrimidin-2-
yl]amino}cyclohexyl)urea;
N-(2,6-dibromo-4-isopropylphenyl)-N'-(cis-4-{[4-(dimethylamino)-pyrimidin-2-
y I ] am ino} cy c lohexy 1 )urea;
N-[3 -(cyclopentyloxy)-4-methoxypheny l]-N'-(cis-4- {[4-( dimethyl am ino)-
pyrimidin-2-yl]amino}cyclohexyl)urea;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-N'-(2,6-
dimethylphenyl)urea;
N-(2,4-difluorophenyI)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2~
yl]amino}cyclohexyl)methyl]urea;

1022
N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyC1-5hexyl)methyl]-N'-(2-
ethyl-6-methylphenyl)urea;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyI)methyl]-N'-(4-
fluorophenyl)urea;
N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyclohexyI)methyI]-N'-
mesitylurea;
N-[(cis-4-{[4-(dimethy]amino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-N'-
(2,4,6-trichlorophenyI)urea;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)methyl]-N'-
(2,4,6-tribromophenyl)urea;
N-(2,4-dibromo-6-fluorophenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]urea;
N-(2,6-diethyIphenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]urea;
N-[2-chloro-6-(trifluoromethyl)phenyl]-N'-[(cis-4-{[4-(dimethylamino)-pyrimidin-
2-yI]amino}cyclohexyl)methyl]urea;
N-(2-chloro-6-methylphenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]urea;
N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-N'-(2-
ethyl-6-isopropylphenyl)urea;
N-[(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyc!ohexyl)methyI]-N'-(2-
isopropyI-6-methylphenyi)urea;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-N'-(2-
methy I -3 -nitropheny 1 )urea;
N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yI]amino}cyclohexyl)methy!]-N'-(2-
propylphenyl)urea;
N-(2-terl-butyl-6-methylphenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]urea;

1023
N-(2-tert-butylphenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]urea;
N-(3-chloro~2-methyIphenyl)-N'-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]urea;
N-(4-bromo-2,6-difluorophenyl)-N'-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]urea;
N-[4-chloro-2-(trifluoromethyl)phenyl]-N'-[(cis-4-{[4-(dimethylamino)-pyrimidin-
2-yl]amino}cyC1-5hexyl)methyl]urea;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyC1-5hexyl)methyl]-N'-
(diphenylmethyl)urea;
N-(4-bromo-2,6-dimethyIphenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]urea;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yI]amino}cyclohexyl)methyl]-N'-(3-
methyl-5-phenylisoxazol-4-yl)urea;
N-(3,5-dichlorophenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]-
amino}cyclohexyl)methyi]urea;
N-(2,3-dichlorophenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]-
amino}cyclohexyl)methyl]urea;
N-(2,6-diisopropylphenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]-
amino} cyclohexyl)methyl]urea;
N-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]araino}cyclohexyl)methyl]-N'-(2,3-
dimethyl-6-nitrophenyI)urea;
N-(2,6-dibromo-4-fluorophenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]urea;
N-(2,6-dichIorophenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]-
amino}cyclohexyl)methyl]urea;
N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyl)methyl]-N'-(2-
methoxy-5-methylphenyl)urea;

1024
N-[(cis-4-{[4-(dimethyIamino)pyrimidin-2-yl]amino}cyclohexyI)methyl]-N'-(2-
methyl-6-nitrophenyl)urea;
N-(3,4-difluorophenyl)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]-
amino}cyclohexyl)methyl]urea;
N-(3!5-difluorophenyI)-Nl-[(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]-
amino}cyclohexyl)methyl]urea; and
N-(3-chloro-4-fluorophenyI)-N'-[(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)methyl]urea;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
69. The compound according to claim 52 wherein R\ is selected from the group consisting of:
(i) C1-5 alkyl, and
C1-5 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
"C1-5 alkoxy,
(ii) carbocyclyl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•cyano,
•nitro,
•C|_5 alkyl,
•C1-5 alkyl substituted by halogen,

1025
•C]o alkoxy carbonyl,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by halogen,
•mono-C1-5 alkylamino,
•di-C1-5 alkylamino, and
•carbocyclic aryl,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•Chalky!,
•C1-5 alkoxy carbonyl, and
•carbocyclic aryl;
L is Formula (VII);
Y is -C(S)NR5-;
wherein carbocyclic aryl is phenyl or naphthyl;
carbocyclyl is bicyclo[2.2.1]heptyl;
heterocyclyl is 2,3-dihydro-benzo[l,4]dioxinyl, benzo[l,3]dioxolyl,
isoxazolyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
70. The compound according to claim 69 wherein R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-; R5 is hydrogen;
or a pharmaceuticaily acceptable salt, hydrate, or solvate thereof.
71. The compound according to claim 70 wherein K\ is selected from the group consisting of:
carbocyclic aryl, and

1026
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•cyano,
•C1-5 alkyl,
•C1-5 alkoxy,
•mono-Ct-5 alkylaraino, and
*di-C1-5 alkylamino;
wherein carbocyclic aryl is phenyl or naphthyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
72. The compound according to claim 1 selected from the group consisting of:
N-(4-cyanophenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}-
cyclohexyl)thiourea;
N-(2,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]-
amino} cyclohexyl)thiourea;
N-(cis-4- {[4-(dimethylamino)pyrimidin-2-yl]amino} cyclohexyl)-N'-(3,4,5-
tr i methoxy ph eny l)thiourea;
N-(3,4-dimethoxyphenyI)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]-
amino} cyclohexyl)thiourea;
N- [4 -(dimethyl am in o)-1 - naphthyl] -N'-(ds-4- {[4-(dimethy lamino)-pyrimidin-2-
yl]amino}cyclohexyl)thiourea;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-N'-(2,4,6-
tribromophenyl)thiourea;
N-(cis-4-{[4-(dimethylamino)pyrimidin-2-yl]amino}cyclohexyl)-N'-
mesitylthiourea;

1027
N-(4-bromo-2,6-dimethylphenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yljamino} cyclohexyl)thiourea;
N-(5-chIoro-2,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-pyrimidin-2-
yl]amino}cyclohexyl)thiourea;
N-(2,4-dibromo-6-fluorophenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino} cyclohexyl)thiourea; and
N-(2,4-dichloro-6-methylphenyl)-N'-(cis-4-{[4-(dimethylamino)pyrimidin-2-
yl]amino}cyclohexyl)thiourea;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
73. The compound according to claim 52 wherein K\ is selected from the group consisting of:
(i) Ci_8 alkyl, and
Ci-g alkyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkoxy,
•C1-5 alkoxy substituted by carbocyclic aryl,
•carbocyclyl,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro, and
•"C1-5 alkoxy,
(ii) C2o alkenyl,
(iii) carbocyclyl,
(iv) carbocyclic aryl, and

1028
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
-C.5 alkyl,
•C1-5 alkyl substituted by halogen, and
•C1-5 alkoxy;
L is Formula (VII);
Y is -C(O)O-;
wherein carbocyclic aryl is phenyl or naphthyl;
carbocyclyl is 9/7-fluorenyI or menthyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceuttcally acceptable salt, hydrate, or solvate thereof.
74. The compound according to claim 73 wherein R2 is methylamino or dimethylamino; p is 0;
R3 and R4 are hydrogen; A is a single bond; B is a single bond or -CH2-:
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
75. The compound according to claim 2 wherein Q is Formula (IV); p is 1 or 2;
Rj is selected from the group consisting of:
(i) Ci.ie alkyl, and
Cue alkyl substituted by substituent(s) independently selected from the
group consisting of:
•hydroxy,
•oxo,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,

1029
••C1-5 alkyl,
••C1-5 alkyl substituted by halogen, and
••C1-5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
"C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by substituent(s) independently
selected from the group consisting of:
"halogen,
•*C1-5 alkoxy, and
••C1-5 alkyl,
•carbocyclic arylsulfinyl,
•carbocyclic arylsulfinyl substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
•carbocyclic aryl,

1030
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,
"C1-5 alkylcarbonylamino,
••C3-6 cycloalkylcarbonylamino,
"Ci.s alkyl,
•*Ci,5 alkyl substituted by halogen,
"C1-5 alkoxy, and
"C1-5 alkoxy substituted by halogen, and
•heterocyclyl,
(ii) C3-12 cycloalkyl, and
C3.]2 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by substitutent(s) independently selected from
the group consisting of:
" C1-5 alkoxy,
••halogen,
••C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•cyano,
•nitro,
•C1-50 alkyl,

1031
•Ci-io alky! substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••hydroxy,
•Ci_9 alkoxy,
•Ci_9 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••carbocyclic aryl,
•carboxy,
•C1-5 alkoxycarbonyl,
•di-C1-5 alkylamino,
•CN5 alkylcarbonylamino,
*C3-6 cycloalkylcarbonylamino,
•C1-5 alkylthio,
•C1-5 alkylsulfinyl,
•Ci.s alkylsulfonyl,
•carbocyclic aryl,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•amino,
•C1-5alkyl,
•Cj.5 alkyl substituted by halogen,
•C1-5 alkoxy,
•carbocyclic aryloxy,

1032
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••C1-5 alkyl,
••C1-5 alkyl substituted by halogen, and
•*C1-5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by halogen,
•heterocyclyl sulfonyl,
• heterocyclyl sulfonyl substituted by C1-5 alkyl,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•C1-5alkylthio,
•C1-5 alkyl sulfinyl,
•carbocyclic arylsulfinyl,
•carbocyclic arylsulfinyl substituted by halogen,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by substituents(s) independently
selected from the group consisting of:
••halogen,
"C1-5 alkoxy,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
R2 is selected from the group consisting of:
amino, C1-5 alkyl, C1-5 alkoxy, -N(R2a)(R2b), wherein R2a is hydrogen or C1-5 alkyl
and R2b is C1-5 alkyl or C3-6 cycloalkyl;
wherein carbocyclic aryl is phenyl or naphthyl;

1033
heterocyclyl is 3,4-dihydro-l//-isoquinolinyl, benzo[l,3]dioxolyl, fury],
isoxazolyl, oxazoly], pyrazolyl, pyrazinyl, pyridyl, pyrimidyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
76. The compound according to claim 75 wherein Rs is selected from the group consisting of:
(i) C1-16alkyI, and
C1-16 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•oxo,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl,
"C1-5 alkyl substituted by halogen, and
"C1-5 alkoxy, and
••C1-5 alkoxy substituted by halogen,
(ii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
"carbocyclic arylsulfinyl, and
•carbocyclic arylsulfinyl substituted by halogen,
L is Formula (VII);
Y is a single bond or -CH2-;
R2 is -N(R.2a)(R-2b)» wherein R2a is Cj.5 alkyl and R2b is C1-5 alkyl;
carbocyclic aryl is phenyl;
heterocyclyl is pyrazinyl; and

1034
halogen is fluoro, chloro, or bromo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
77. The compound according to claim 76 wherein Ri is selected from the group consisting of:
(i) C1-16 alkyl, and
C1-16 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyciic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen, and
"C1-5 alkoxy,
(ii) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic arylsulfinyi, and
•carbocyclic arylsulfinyi substituted by halogen,
R2 is -N(R2a)(R2b), wherein R?a is C1-5 alkyl and R2b is C1-5 alkyl;
carbocyclic aryl is phenyl;
heterocyclyl is pyrazinyl; and
halogen is fluoro or bromo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
78. The compound according to claim 77 wherein R] is selected from the group consisting of:
heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic arylsulfinyi, and

1035
•carbocyclic arylsulfinyl substituted by halogen,
R? is -N(R2a)(R2b), wherein R2a is C1-5 alkyl and R2b is C1-5 alkyl;
carbocyclic aryl is phenyl;
heterocyclyl is pyrazinyl; and
halogen is fluoro;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
79. The compound according to any one of claims 76 to 78 wherein p is 1 and T is C1-5 alkyl;
R3 and R4 are both hydrogen; A and B are both single bonds:
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
80. The compound according to claim 1 selected from the group consisting of:
N -{cis-4-[(3,5-dimethoxybenzyl)amino]cyclohexyl}-N ,N ,5-
trimethylpyrimidine-2,4-diamine;
N2-{cis-4-[(3-bromobenzyl)amino]cyclohexyl}-N4,N4,5,6-tetramethylpyrimidine-
2,4-diamine;
N2-{cis-4-[(3,4-difluorobenzyl)amino]cyclohexyl}-N4,N4,5,6-
tetramethylpyrimidine-2,4-diamine; and
N2-[cis-4-({6-[(3,4-difluorophenyl)sulfinyl]pyrazin-2-yl}amino)cyclohexyl]-
N4,N4,5-trimethyIpyrimidine-2,4-diamine;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
81. The compound according to claim 1 is:
N2-[cis-4-({6-[(3,4-difIuorophenyl)sulfinyl]pyrazin-2-yl}amino)cyclohexyl]-
N4,N4,5-trimethylpyrimidine-2,4-diamine;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
82. The compound according to claim 75 wherein Ri is selected from the group consisting of:

1036
(i) C1-16 alkyl, and
Ci.]6 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•hydroxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••C1-5 a'kyl,
••C1-5 alkyl substituted by halogen, and
••C|_5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
"C1-5 alkoxy, and
••C1-5 alkyl,
•carbocyclic arylsulfmyl,
•carbocyclic arylsulfmyl substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
••C1-5 alkyl, and

1037
••C1-5 alkyl substituted by halogen,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by substituent(s) independently
selected from the group consisting of:
"halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl,
••C1-5 alkyl substituted by halogen, and
••C1-5 alkoxy,
(ii) C3.]2 cycloalkyl, and
C3-12 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by substitutent(s) independently selected from
the group consisting of:
•• C1-5 alkoxy,
••halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,

1038
•cyano,
•nitro,
•C1-50 alkyl,
•Cj.io alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
"hydroxy,
•C]_9 alkoxy,
•C1.9 alkoxy substituted by halogen,
•carboxy,
•C1-5 alkoxycarbonyl,
•di-C1-5 alkylamino,
•C1-5 alkylcarbonylamino,
"C3-6 cycloalkylcarbonylamino,
•C1-5 alkylsulfonyl, and
•carbocyclic aryl,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•hydroxy,
•amino,
•C1-5 alkyl,
•Cj.g alkyl substituted by halogen,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:

1039
—halogen,
••C1-5alkyl,
••C1-5 alkyl substituted by halogen, and
••C1-5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by halogen,
"heterocyclyl sulfonyl,
• heterocyclyl sulfonyl substituted by C\.s alkyl,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by halogen,
•C1-5 alkylthio,
•C1-5 alkylsulfmyl,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by substituents(s) independently
selected from the group consisting of:
••halogen,
"C1-5 alkoxy,
••C1-5 alkyl, and
••C|.5 alkyl substituted by halogen,
L is Formula (VII);
Y is -C(O)-;
R2 is selected from the group consisting of:
amino, C1-5 alkyl, C1-5 alkoxy, -N(R2a)(R2b), wherein R2a is hydrogen or C,_5 alkyl
and R2b is C1-5 alkyl or C3-6 cycloalkyl;
wherein carbocyclic aryl is phenyl;
heterocyclyl is benzo[l,3]dioxolyl, furyl, isoxazolyl, oxazolyl, pyrazolyl,
pyrazinyl, pyridyl, pyrimidyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;

1040
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
83. The compound according to claim 82 wherein Ri is selected from the group consisting of:
(i) Cue alkyl, and
C].]6 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•hydroxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
•"C1-5 alkyl,
••C1-5 alkyi substituted by halogen, and
••C1-5 alkoxy,
•heterocyc ly loxy,
•heterocyclyloxy substituted by halogen,
•mono-carbocyclic arylamino,
•mono-carbocyclic arylamino substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
••C1-5 alkoxy, and
••C1-5 alkyl,
•carbocyclic arylsulfinyl,
•carbocyclic arylsulfinyl substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
•*C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,

1041
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by substituent(s) independently
selected from the group consisting of:
••C1-5 alkyl, and
••C]-5 alkyl substituted by halogen,
•carbocyclic aryl.,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
"halogen,
"C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
(ii) C3-12 cycloalkyl, and
C3-12 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by substitutent(s) independently selected from
the group consisting of:
•• C1..5 alkoxy,
••halogen,
"C1-5 alkyl, and
••C]o alkyl substituted by halogen,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•cyano,
•nitro,
•C1-50 alkyl,

1042
•CJ.IO alkyl substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••hydroxy,
•C1.9 alkoxy,
•C1.9 alkoxy substituted by halogen,
•carboxy,
•C1-5 alkoxycarbonyl, and
•C1-5 alkylsulfonyl,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•C1-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
••C1-5 alky!,
"C1-5 alkyl substituted by halogen, and
••C1-5 alkoxy,
•heterocyclyloxy,
•heterocydyloxy substituted by halogen,
•heterocyclyl sulfonyl,
• heterocyclyl sulfony! substituted by C1-5 alkyl,
•mono-carbocyclic arylamino,

1043
•mono-carbocyclic arylamino substituted by halogen,
•C1-5 alkylthio,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by substituents(s) independently
selected from the group consisting of:
••halogen,
"C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
R2 is selected from the group consisting of:
C1-5 alkoxy, -N(R2a)(R2b), wherein R2a is hydrogen or C1-5 alkyl and R2b is C1-5
alky];
wherein carbocyclic aryl is phenyl;
heterocyclyl is benzo[l,3]dioxolyl, furyl, isoxazolyl, oxazolyl, pyrazolyl,
pyridyl, or thienyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
84. The compound according to claim 83 wherein R] is selected from the group consisting of:
(i) C1-16 alkyl, and
C1-16 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•hydroxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,
-C1-5 alkyl,
••C1-5 alkyl substituted by halogen, and

1044
••C|.5 alkoxy,
•heterocyclyloxy,
•heterocyclyloxy substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
•■C1-5 alkyl substituted by halogen,
•mono-carbocyclic arylamino,
•mono-carbocyclic aryiamino substituted by substituent(s) independently
selected from the group consisting of:
"halogen,
••C1-5 alkoxy, and
••C1-5 alkyl,
■carbocyclic arylsulfmyl,
•carbocyclic arylsulfinyl substituted by substituent(s) independently
selected from the group consisting of:
••halogen,
••C1-5 alkyl, and
"C1-5 alkyl substituted by halogen,
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
(ii) C3-12 cycloalkyl, and
C3-12 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:

1045
•carbocyclic aryl, and
•carbocyclic aryl substituted by substitutent(s) independently selected from
the group consisting of:
••C1-5 alkoxy,
••halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
(iii) carbocyclic aryl, and *
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•cyano,
•nitro,
•C1-5O alkyl,
•Ci_10 alkyl substituted by halogen,
•C]_g alkoxy, and
•Ci_9 alkoxy substituted by halogen,
(iv) heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•halogen,
•0,-5 alkyl,
•C1-5 alkyl substituted by halogen,
•C1-5 alkoxy,
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen,

1046
»C1-5 alkyl,
••C1-5 alkyl substituted by halogen, and
••C1-5 alkoxy,
•Ci-s alkylthio,
•carbocyclic arylsulfonyl,
•carbocyclic arylsulfonyl substituted by halogen,
R2 is selected from the group consisting of:
-N(R2a)(R2b), wherein R2a is hydrogen or C1-5 alkyl and R2b is C1-5 alkyl;
wherein carbocyclic aryl is phenyl;
heterocyclyl is benzo[l,3]dioxolyl, furyl, pyrazolyl, pyridyl, or thienyl;
and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
85. The compound according to any one of claims 82 to 84 wherein p is 1 and T is C1-5 alkyl;
R3 and R4 are both hydrogen; A is a single bond and B is a single bond or -CH2-;
or a pharmaceutical ly acceptable salt, hydrate, or solvate thereof.
86. The compound according to claim 1 selected from the group consisting of:
N-[(cis-4-{[4-(dimethylammo)-5-methylpyrimidin-2-
yI]amino}cyclohexyl)methyl]-3,5-bis(trifluoromethyl)benzamide;
N-[(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)methyl]-3,5-bis(trifluoromethyl)benzamide;
N-[(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)methyl]-3,4-difluorobenzamide;
3,5-dichloro-N-[(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)methyl]benzamide;

1047
N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)methyl]-3,4-difluorobenzamide;
N-[(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)methyI]-3,5-dimethoxybenzamide;
N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yI]amino}cyclohexyl)methyl]-3-fIuoro-4-methylbenzamide;
N-[(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yI]amino}cyclohexyl)methy]]-3-(trifluoromethyl)benzamide;
N-[(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)methyl]-3-(trifluoromethoxy)benzamide;
4-bromo-N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yI]amino}cyclohexyl)methyl]-3-methylbenzamide;
N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)methyI]-3-fluoro-4-(trifluoromethyl)benzamide;
3,5-dichloro-N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)methyl]benzamide;
3,4-dichloro-N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyc]ohexyl)methyl]benzamide;
4-chloro-N-[(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)methyl]benzamide;
4-chIoro-N-[(cis-4-{[4-{dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)methyl]benzamide;
N-[cis-4-({[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}methyI)cyC1-5hexyl]-3,5-dimethoxybenzamide;
4-bromo~N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}methyl)cyclohexyl]benzamide;
4-bromo-N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}methyl)cyctohexy!]-3-methylbenzamide;

1048
3,5-dichIoro-N-[cis-4-({[4-(dimethyIamino)-5-methylpyrimidin-2-
y!]amino}methyl)cyclohexyl]benzamide;
3,4-dichioro-N-[cis-4-({[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}methyl)cyclohexyl]benzamide;
N-[cis-4-( {[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}methyl)cyC1-5hexyl]-3,5-bis(trifluoromethyl)benzamide;
N-[cis-4-({[4-(dimethyiamino)-6-methylpyrimidin-2-
yl]amino}methyl)cyclohexyl]-3,4-difluorobenzamide;
4-bromo-N-[cis-4-({[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}methyl)cyclohexyl]benzamide;
4-bromo-N-[cis-4-({[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}methyI)cyclohexyl]-3-methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yI]amino}cyclohexyl)-2-(2-
fluorophenoxy)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyI)-3,4,5-
tri methoxybenzam ide;
N-(4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}cyclohexyl)-3-
nitrobenzamide;
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}cyclohexyI)-2,2-
diphenylacetamide;
N-(cis-4-{[4-(dimethylamino)-6~methylpyrimidin-2-yl]amino}cyclohexyl)-4-
methylbenzamide;
4-chIoro-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
3-chIoro-N-(cis-4-{[4-(dimethyiamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3;4-
difluorobenzamide;

1049
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyc]ohexyl)-3-
methylbenzaraide;
N-(cis-4- {[4-(dimethyIamino)-6-methylpyrimidin-2-y I]amino} cyC1-5hexyl)-3 -
methoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
fluorobenzamide;
N-(cis-4-{[4-(diraethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-3-
methylbenzamide;
N-(cis-4-{[4-tdimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
methoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-4-
methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-3,4-
difluorobenzamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(3-
methylphenoxy)nicotinamide;
2-(4-bromophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
2-(4-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-2-(4-
fluorophenoxy)nicotinamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-t3-
fluorophenoxy)nicotinamide;
2-(2-bromophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;

1050
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(3-
methoxyphenoxy)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexy!)-2-(4-
methoxyphenoxy)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yI]amino}cyC1-5hexyl)-2-(4-
iodophenoxy)nicotinamide;
2-(3,4-dichlorophenoxy)-N-(cis-4-{[5-methyl-4-(methylamino)pyrimidin-2-
yl]amino}cyclohexyl)acetamide;
2-(2,3-dichlorophenoxy)-N-(cis-4-{[5-methyl-4-(methylamino)pyrimidin-2-
y 1 ] am ino} eye 1 ohexy I)acetam ide;
2-[(3,4-difluorophenyl)sulfonyl]-N-(cis-4-{[4-(dimethyIamino)-5-
methyIpyrimidin-2-yl]amino}cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-ethylpyrimidin-2-yl]amino}cyclohexyI)-3,4-
difluorobenzamide;
N-[cis-4-({4-[ethyl(methyI)amino]-5-methylpyrimidin-2-yl}amino)cyclohexyi]-
3?4-difIuorobenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyI)-3,5-
dimethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methy]pyrimidin-2-yl]amino}cyC1-5hexyl)-2-(2-
methoxyphenoxy)nicotinamide;
2-t2-chlorophenoxy)-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)'5-methylpyrimidin-2-
yl]amino}cyclohexyi)nicotinamide;
2-(3-bromophenoxy)-N-(cis-4-{[4-(dimethylamino>5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
N-(cis-4~{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-2-[3-
(trifluoromethyl)phenoxy]nicotinamide;

1051
N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yI]amino}cyclohexyl)-2-(3-
fluorophenoxy)acetamide;
N-tcis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yt]amino}cyclohexyi)-2-(3-
methoxyphenoxy)acetamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-y)]amino}cyclohexyl)-2-[3-
(trifluoromethyl)phenoxy]acetamide;
2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yl]amino}cyclohexyl)acetamide;
2-[(5-chloropyridin-3-yl)oxy]-N-(cis-4-{[4-(dimethylamino)-5-methy]pyrimidin-2-
y ljamino} cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3,4-
difluorobenzamide;
2-(3,4-difluorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-hydroxyacetamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-
hydroxy-2-(4-methoxyphenyl)acetamide;
2-(2,3-difluorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yI]amino}cyclohexyl)-2-hydroxyacetamide;
N-(cis-4-{[4-(dimethylamino)~5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-
hydroxy-2-[3'(trifluoromethyI)phenyl]acetamide;
N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-2-{[2-
(trifluoromethyl)phenyl]sulfinyl}acetamide;
2-[(2-chlorophenyI)suIfinyl]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)acetamide;
2-[(3-bromophenyI)swlfinyI]-N-(cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-
y]]amino}cyclohexyl)acetamide;
2-[(3,4-difluorophenyl)sulfinyl]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-
2-yl]amino}cyclohexyl)acetamide;

1052
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyc]ohexyl)-3-
fluorobenzamide;
3-bromo-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yI]amino}cyclohexyI)-4-
(trifl uoromethoxy)benzami de;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-4-
fluorobenzamide;
3,4-dichloro-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
bis(trifiuoromethyl)benzamide;
N-(cis-4'{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
dimethoxybenzamide;
N-(cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2,4-
difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-2,5-
difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyI)-2,3,4-
trifluorobenzamide;
4-chloro-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino} cyclohexyl)benzamide;
3-cyano-N-(cis-4-{[4'(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
4-cyano-N-(cis-4-{[4'(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;

1053
2-[(3,4-dichlorophenyl)sulfinyl]-N-(cis"4-{[4-(dimethyIamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)acetamide;
N-tcis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-{[3-
(trifluoromethyl)phenyl]sulfinyl}acetamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-{[3-
(trifluoromethyl)phenyl]sulfonyl}acetamide;
N-(cis-4-{[4-(dimethy]amino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-2-
(isopropylthio)nicotinamide;
2-(tert-butylthio)-N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-
(propylthio)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-3-
(methylsulfonyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}cyclohexyl)-3-
fl uorobenzamide;
N-(cis-4-{[4'(dimethylamino)-6-methyIpyrimidin-2-yl]amino}cyC1-5hexyl)-3-
(trifluoromethyl)benzamide;
3-cyano-N-(cis-4-{[4-(dimethylamino)-6-methyJpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
4-cyano-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethy]amino)-5,6-dimethylpyrimidin-2-
y ljamino} cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethyl)benzamide;
3-cyano-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino}cyclohexyi)benzamide;

1054
N-(cis-4-{[4-(dimethyiamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
methylbenzamide;
3-chloro-N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-
y ljamino} cyclohexyl)benzamide;
3-bromo-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yI]amino}cyclohexyl)-3,5-
dimethoxybenzamide;
N-(cis-4-{[4-(dimethyIamino)-556-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
bis(trifluoromethyl)benzamide;
354-dichlorO"N-(cis-4-{[4-(dimethylamino)-5;6-dimethylpyrimidin-2-
yljamino} cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-4-
(trifluoromethoxy)benzamide;
4-cyano-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cts-4-{[4-(dtmethy!amino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-4-
methy Ibenzam ide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyI)-4-
fluorobenzamide;
4-chloro-N-(cis-4- {[4-(dimethyIamino)-5,6-dimethyIpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-2-
methoxybenzamide;
4-bromo-N-(cis-4-{[4-(dtmethylamino)-5-methyIpyrimidin-2-
y ljamino} cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
(tr i flu oromethy 1 )benzam ide;

1055
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yI]amino}cyc]ohexyl)-3-
methoxybenzamide;
5-bromo-N-(cis-4-{[4-(dimethyIamino)-5,6-dimethyIpyrimidin-2-
yl]amino}cyclohexyl)-2-furamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyC1-5hexyI)-5-
methyIisoxa2ole-3-carboxamide;
2-(3,5-difluorophenyI)-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino}cyclohexyl)-2-hydroxyacetamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethyIpyrimidin-2-yl]amino}cyclohexyI)-2-
methyl-l,3-oxazole-4-carboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethyIpyrimidin-2-yl]amino}cyC1-5hexyl)-2,6-
dimethoxynicotinamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyI)-4-
(trifluoromethy !)benzam ide;
4-bromo-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino}cyclohexyI)-3-methyIbenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-diniethylpyrimidin-2-yl]amino}cyclohexyl)-3-
fluoro-4-methy Ibenzam ide;
N'(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]amino}cyC1-5hexyl)-4-
fluoro-3 -methyl benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
ethylbenzamide;
N'(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethoxy)benzam ide;
5-bromo-N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;

1056
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-5-
methylthiophene-2-carboxamide
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yI]amino}cyC1-5hexyl)-6-
(trifluoromethyl)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethy]pyrimidin-2-yl]amino}cyclohexyl)-3;5-
diethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyC1-5hexyl)-3-
ethoxy benzam ide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
isopropoxybenzamide;
3,5-dichloro-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
y)]amino}cyclohexyl)-3-methylbenzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yI]amino}cyC1-5hexyl)-4-
ethoxybenzamide;
N-(cis-4'{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-4-
fluoro-3-methyIbenzamide;
N-(cis-4'{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
fluoro-4-methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yt]amino}cyclohexyl)-3-
ethylbenzamide;
N-(cts-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
bis(trifluorom ethyl )benzamide;
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
fluoro-4-(trifluoromethy])benzamide;
N-(cis-4-{[4-(dimethyIamino)-6-methy)pyrimidin-2-yI]amino}cyclohexyl)-3-
fluoro-5-(trifluoromethyI)benzamide;

1057
3-chloro-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)-4-fluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
fluoro-3-methyIbenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}cyclohexyl)-3-
fluoro-4 -methyl benzamide;
3,5-dichloro-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yI]amino}cyclohexyl)-3-
(tri fluororaethoxy)benzam i de;
N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yI]amino}cyclohexyl)-3,5-
difluorobenzamide;
4-bromo-N-(cis-4-{[4-(dimethy!amino)-6-methylpyrimidin-2-
yI]amino}cyclohexyl)-3-methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-3-
ethylbenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}cyclohexyl)-4-
(trifluoromethyl)benzamide;
4-bromo-N-(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino} cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
ethylbenzamide;
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]araino}cyclohexyl)-3,5-
diethoxybenzamide;
N-(cis-4-{[4-(dimethykmino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
ethoxybenzamide;
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
isopropoxy benzamide;

1058
5-bromo-N-(cis-4-{[4-(dimethy]amino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cydohexyl)-2-furamide;
5-chloro-N-(cis-4- {[4-(dimethyIamino)-6-methyIpyrimidin-2-
yl]amino}cyclohexyl)-2-furamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-3-
fluoro-5-(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-2,2-
difluoro-l,3-benzodioxoIe-5-carboxamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyi)-3-
ethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyI)-3-
isopropoxybenzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyI)-2-furamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-3,5-
diethoxybenzamide;
4-chloro-N-(cis-4-{[4'(dimethy!amino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-3-(triftuoromethyl)benzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
3,4-dichloro-N-(cis-4-{[4-(dimethylamino)-6-methyipyrimidin-2-
yl]amino}cyc!ohexyl)benzamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-4-(trifluoromethoxy)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-4-
methoxy-3-(trifluoromethyl)benzamide;

1059
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
methoxy-3-(trifluoromethyl)benzamide;
2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-methylpropanamide;
l-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
l-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclobutanecarboxamide;
l-(2,4-dichlorophenyl)"N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
2-(4-chIorophenyl)-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyI)-2-methyIpropanamide;
l-(4-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidJn"2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
l-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclobutanecarboxamide;
l-(2,4-dichlorophenyI)-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
2-[3,5-bis(trifluoromethyl)phenyl]-N-(cis-4-{[4-(dimethylamino)-6-
methyIpyrimidin-2-y!]amino}cyC1-5hexyi)acetamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
[2,2,2-trifluoro-1 -hydroxy-1 -(trifluoromethyl)ethyl]benzamide;
2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yi]amino}cyc!ohexyl)-l-(4-
methylphenyl)cyclopropanecarboxamide;
2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethyIaraino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)propanamide;

1060
2-(4-chIorophenyl)-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-hydroxyacetamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-l-(4-
methoxyphenyl)cyc]opropanecarboxamide;
N2-(3-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)-N2-methylgIycinamide;
N2-(3,4-dichlorophenyl)-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)-N2-methyIglycinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-N2-
methyl-N2-(3-methylphenyl)glycinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N2-(3-
fluorophenyl)-N -methylglycinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-N2-(4-
fluorophenyl)-N2-methylglycinamide;
N2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyc!ohexyI)-N2-methyIglycinamide;
N2-(3,4-difIuorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yI]amino}cyclohexyl)-N2-methylglycinamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyl)-N2-(3-
methoxyphenyI)-N -methylglycinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N"-(4-
methoxyphenyI)-N -methylglycinamide;
2-[(3,4-difIuorophenyl)amino]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-
2-yl]amino}cyclohexyI)nicotinamide;
2-(3,4-dichlorophenoxy)-N-(cis-4-{[4-methyl-6-(methylamino)pyrimidin-2-
yl]amino} cyclohexyl)acetamide;
trans-2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;

1061
trans-2-(3-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
trans-2-(3,4-difluorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
trans-2-(3,4-dichIorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
trans-2-[3,5-bis(trifluoromethyi)phenyl]-N-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)cyclopropanecarboxamide;
2-[(4-chlorophenyl)sulfonyl]-N-(cis'4-{[4-(diraethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
2-[(3-chlorophenyl)sulfonyl]-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
2-[(4-bromophenyl)sulfonyl]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-{[4-
(trifluoromethyl)phenyl]suifonyl}nicotinamide;
N-tcis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-2-{[l-
methyI-3-(trifluoromethyI)-lH-pyrazol-5-yl]oxy}acetamide;
2-[(2-chlorophenyI)sulfonyl]-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
y]]amino}cyclohexyl)nicotinamide;
2-[(3-chlorophenyl)suIfonyI]-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
3,4-dichloro-N-{cis-4-[(4-methoxy-5-methyIpyrimidin-2-
yl)amino]cyclohexyl}benzamide;
N-[cis-4-(4-dimethyIamtno-5-methyI-pyrimidin-2-ylamino)-cyclohexyl]-2-
phenoxy-nicotinamide;
N-[cis-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-cyclohexyl]-2-
phenoxy-nicotinamide;

1062
3-chIoro-N-[cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
4-fluoro-benzamide;
4-chloro-N-[cis-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
3-fluoro-benzamide;
3-chIoro-N-[cis-4-(4-dimethyIamino-6-methyI-pyrimidin-2-ylamino)-cyclohexyI]-
5-fluoro-benzamide;
N-[cis-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-cyclohexyl]-3,4,5-
trifluoro-benzamide;
3-chloro-4-fluoro-N-[cis-4-(5-methyl-4-methylamino-pyrimidin-2-ylamino)-
cyclohexyij-benzamide;
4-chloro-N-[cis-4-(4-dimethylamino-5-methyI-pyrimidin-2-yIamino)-cyclohexyi]-
3-fluoro-benzamide;
3-chIoro-N-[cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
5-fluoro-benzamide;
N-[c is-4-(4-dimethylamino-5-methyl-pyrimidin-2-yIamino)-cyclohexyl] -3,4,5 -
trifluoro-benzam ide;
N-[cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyC1-5hexyl]-3,5-
difluoro-benzamide; and
2-{3,4-difluoro-phenyI)-N-[cis-4-(4-dimethylamino-5-methyI-pyrimidin-2-
ylamino)-cyclohexyl]-acetamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
87. The compound according to claim 1 selected from the group consisting of:
N-[(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyC1-5hexyI)methyl]-3,5-bis(trifluoromethyl)benzamide;
N-[(cis-4- {[4-(dimethylamino)-5-methy lpyrimidin-2-
yl]amino}cyclohexyl)methyl]-3,5-dimethoxybenzamide;

1063
N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)methyl]-3-(trifluoromethyl)benzamide;
4-bromo-N-[(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyC1-5hexyI)methyl]-3-methylbenzamide;
3,5-dichloro-N-[(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)methyl]benzamide;
3,4-dichloro-N-[(cis-4-{[4-(dimethylamino)-5-methytpyrimidin-2-
yl]amino}cyclohexyl)methyl]benzamide;
3,5-dichloro-N-[cis-4-({[4-(dimethylamino)-5-raethylpyrimidin-2-
yl]amino}methyl)cyclohexyl]benzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(2-
fluorophenoxy)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3,4,5-
trimethoxybenzamide;
N-(4-{[4-(dimethy!amino)-6-methylpyrimidin-2-yl]amino}cyC1-5hexyI)-3-
nitrobenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-2,2-
diph enyl acetam ide;
4-chloro-N-(cis-4-{[4-(dimethyiamino)-6-methylpyrimidin-2-
y I]amino} cyclohexyl)benzamide;
3-chIoro-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}cyC1-5hexyl)-3;4-
difluorobenzamide;
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrin)idin-2-yl]amino}cyclohexyl)-3-
methylbenzamtde;
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
methoxyben zam ide;

1064
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yI]amino}cyclohexyI)-4-
fluorobenzamide;
N-(cis-4-{[4-(dimethy]amino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-3-
m ethyl benzamide;
N-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino} cyc!ohexyl)-3 -
methoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-y]]amino}cyclohexyl)-4-
methy I benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3,4-
di fluorobenzamide;
3-chloro-N-(cis'4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yljamino} cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(3-
methylphenoxy)nicotinamide;
2-(4-bromophenoxy)~N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
2-(4-chIorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yl]amino}cyclohexyi)nicotinamide;
N-(cis-4-{[4-(dimethy]amino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-2-(4-
fluorophenoxy)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-2-(3-
fluorophenoxy)nicotinamide;
2-(2-bromophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(3-
methoxyphenoxy)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(4-
methoxyphenoxy)nicotinamide;

1065
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(4-
iodophenoxy)nicotinamide;
2-(3,4-dichIorophenoxy)-N-(cis-4-{[5-methyl-4-(methylamino)pyrimidin-2-
yl]amino}cyclohexyl)acetamide;
2-(2,3-dichlorophenoxy)-N-(cis-4-{[5-methyl-4-(methylamino)pyrimidin-2-
yl]amino}cyclohexyl)acetamide;
2-[(3,4-difluorophenyI)sulfonyl]-N-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-y!]amino}cyclohexyl)nicotinamide;
N-[cis-4-({4-[ethyl(methyl)amino]-5-methylpyrimidin-2-yl}amino)cyclohexyi]-
3,4-difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
dimethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(2-
methoxyphenoxy)nicotinamide;
2-(2-chIorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
2-(3-chiorophenoxy)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexy])nicotinamide;
2-(3-bromophenoxy)-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-[3-
(trifluoromethyl)phenoxy]nicotin amide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexy!)-2-(3-
fluorophenoxy)acetamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-(3-
methoxyphenoxy)acetamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-[3-
(trifluoromethy!)phenoxy]acetamide;

1066
2-(3-chlorophenoxy)-N-(cis-4-{[4-(dimethyiamino)-5-methyIpyrimidin-2-
yl]amino}cyC1-5hexyl)acetamide;
2-[(5-chloropyridin-3-yI)oxy]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino} cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yI]amino}cyC1-5hexyl)-3,4-
difluorobenzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yI]amino}cyclohexyI)-2-
hydroxy-2-(4-methoxyphenyl)acetamide;
2-(253-difluorophenyl)-N-(cis-4-{[4-(dimethylatnino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-hydroxyacetamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-2-
hydroxy-2 -[3 -(tr ifl uoromethy l)pheny 1 ] acetam id e;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyclohexyI)-2-{[2-
(trifluoromethyl)phenyl]sulfinyl}acetamide;
2-[(2-chlorophenyI)sulfmyl]-N-(cts-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)acetamide;
2-[(3-bromophenyl)sulfinyl]-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)acetamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-3-
fluorobenzamide;
3-bromo-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
(trifluoromethoxy)benzamide;
N-tcis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
fluorobenzamide;

1067
3,4-dichloro-N-(cis-4-{[4-(dimethyIamino)-5-methy]pyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}cyctohexyl)-3,5-
bis(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methy]pyrimidin-2-yl]amino}cyclohexyl)-3,5-
dimethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2,4-
difluorobenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-2,5-
difluorobenzamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-2,3,4-
tri fl uorobenzam ide;
4-chloro-N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-
yl]amino} cyclohexyl)benzamide;
3-cyano-N-(cis-4- {[4-(dimethy lamino)-5-methylpyrimidin-2-
yljamino} cyclohexyl)benzamide;
4-cyano-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yljamino} cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2-
(isopropylthio)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrtmidin-2-yl]amino}cyclohexyl)-2-
(propylthio)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethyl)benzamide;
3-cyano-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
4-cyano-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yljamino} cyclohexyl)benzamide;

1068
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyI)-3-
(trifluoromethyl)benzamide;
3-cyano-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yI]amino}cyC1-5hexyI)-3-
methylbenzamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
3-bromo-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
y]]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5,6~dimethylpyrimidin-2-yi]amino}cyC1-5hexyI)-3,5-
dimethoxybenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexy])-3,5-
bis(trifluoromethyi)benzamide;
3,4-dichloro-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yljamino} cyclohexyl)benzamide;
4-cyano-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yljamino} cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yI]amino}cyC1-5hexyl)-4-
methylbenzamide;
N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-yI]amino}cyC1-5hexyl)-4-
fluorobenzamide;
4-chloro-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methy!pyrimidin-2-yl]amino}cyclohexyI)-4-
(trifl uoromethy l)benzam i de;

1069
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-y]]amino}cyclohexyl)-3-
methoxybenzam i de;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-
yI]amino}cyclohexyI)-2-furamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexy])-2,6-
dimethoxynicottnamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)-5,6-dimethyIpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5J6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-4-
(trifluoromethyl)benzamide;
4-bromo-N-(cis-4-{[4-(dimethyIamino)-5,6-dimethylpyrimidin-2-
yI]amino}cyclohexyl)-3-methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
fluoro-4-methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-4-
fIuoro-3-methyIbenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethyIpyrimidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethoxy)benzam i de;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5,6-dimethyIpyrimidin-2-
yl]amtno}cyclohexyl)nicotinamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyC1-5hexyl)-5-
methy 1th iophene-2 -c arboxamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
diethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethyIpyrimidin-2-yl]amino}cyclohexyl)-3-
ethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-2-yl]amino}cyclohexyl)-3-
i sopropoxyben zam ide;

1070
3,5-dichloro-N-(cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
4-bromo-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-3-methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
fluoro-3-methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin~2-yl]amino}cyclohexyI)-3-
fluoro-4-methyIbenzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-3-
ethylbenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
bis(trifluoromethyl)benzamide;
N-(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-y l]amino} cyclohexyl)-3 -
fluoro-4-(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
fluoro-5-(trifluoromethyl)benzamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)-4-f!uorobenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
fluoro-3-methylbenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyI)-3-
fluoro-4-methyl benzamide;
3,5-dichloro-N-(cis-4-{[4-(dimethylamino)-6-methylpyriraidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
(trifluoromethoxy)benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
difluorobenzamide;

1071
4-bromo-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)-3-methyIbenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
ethylbenzamide;
4-bromo-N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
ethylbenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3,5-
diethoxybenzamide;
N-(cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
ethoxybenzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-3-
isopropoxybenzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yI]amino}cyclohexyl)-2-furamide;
5-chloro-N-(cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-
yI]amino}cyc!ohexyl)-2-furamide;
N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
fluoro-5-(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-2,2-
difluoro-l,3-benzodioxole-5-carboxamide;
N-(cis-4-{[4-(dimethyiamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-3-
ethoxy benzam ide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-furamide;

1072
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-3,5-
d i ethoxy benzam ide;
4-chloro-N-(cis-4-{[4-(dimethylamino)-5-methy]pyrimidin-2-
yl]amino}cyclohexyI)-3-(trifIuoromethyl)benzamide;
5-bromo-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
y]]amino}cyclohexyl)nicotinamide;
3,4-dichloro-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino} cyclohexyl)benzamide;
3-chloro-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yI]amino}cyclohexyl)-4-(trifluoromethoxy)benzamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
methoxy-3-(trifluoromethyl)benzamide;
N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}cyclohexyl)-4-
methoxy-3-(trifluoromethyI)benzamide;
2-(4-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)-5-methy]pyrimidin-2-
yl]amino}cyC1-5hexyI)-2-methylpropanamide
l-(4-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
l-(4-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclobutanecarboxamide;
l-(2,4-dichlorophenyI)-N-(cis-4-{[4-(dimethylamino)-5-methy]pyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)-2-methylpropan amide
l-(4-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
1 -(4-chlorophenyI)-N-(cis-4- {[4-(dtmethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclobutanecarboxamide;

1073
l-(2,4-dichlorophenyl)-N-(cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
2-(4-chiorophenyl)-N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-
yl]amino}cyclohexy])acetamide;
N-(cts-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-l-(4-
m ethy lpheny 1 )cy clopropanecarboxamid e;
2-(4-chlorophenyI)-N-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-
yl]amino}cyclohexyl)propanamide
2-(4-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-
yl]amino}cyc!ohexyl)-2-hydroxyacetamide;
N-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino} cyclohexyl)-1 -(4-
methoxyphenyl)cyclopropanecarboxamide;
N2-(3-chlorophenyt)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-N2-methylglycinamide;
N2-(3,4-dichIorophenyl)-N-(cis-4-{[4-(din)ethylamino)-5-methylpyrimidin-2-
yl]amino}cyc!ohexyl)-N2-methylglycinamide;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-N"-
methyl-N2-(3-methyIphenyl)glycinamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yI]amino}cyclohexyI)-N2-(3-
fluorophenyI)-N"-methylgIycinamide;
N-(cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-y]]amino}cyclohexyI)-N"-(4-
fluorophenyl)-N2-m ethyl glycinamide;
N2-(4-chlorophenyI)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)-N2-methylglycinamide;
N2-(3,4-difIuorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-N2-methylglycinamide;
N-(cis-4-{[4-(dimethylamino)-5-methy]pyrimidin-2-yl]amino}cyclohexyl)-N2-(3-
methoxyphenyl)-N2-methyIgIycin amide;

1074
2-(3,4-dichIorophenoxy)-N-(cis-4-{[4-methyl-6-(methyIamino)pyrimidin-2-
yl]amino}cyC1-5hexyl)acetamide;
trans-2-(4-chIorophenyI)-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
trans-2-(3-chlorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
trans-2-(3,4-difluorophenyl)-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
trans-2-(3,4-dichlorophenyl)-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)cyclopropanecarboxamide;
trans-2-[3,5-bis(trifluoromethyl)phenyl]-N-(cis-4-{[4-(dimethylamino)-5-
methyipyrimidin-2-yl]amino}cyclohexyl)cyclopropanecarboxamide;
2-[(4-chlorophenyl)sulfonyl]-N-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)nicotinamide;
N-(cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino} cydohexyl)-2- {[ 1 -
methyi-3-(trifluoromethyI)-lH-pyrazoI-5-yI]oxy}acetamide;
N-[cis-4-(4-dimethy!amino-5-methyl-pyrimidin-2-ylamino)-cyC1-5hexyI]-2-
phenoxy-nicotinamide;
N- [cis-4-(4-di methyl amino-6-methyl-pyrimidin-2-y lam ino)-cyclohexyl] -2-
phenoxy-nicotinamide;
3-chloro-N-[cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
4 -fl uoro-benzami de;
4-chloro-N-[cis-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
3-fluoro-benzamide;
3-chloro-N-[cis-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
5-fluoro-benzamide;
N-[cis-4-(4-dimethylamino-6-methyl-pyrimidin-2-ylamino)-cyclohexyl]-3,4,5-
trifluoro-benzamide;

1075
3-chloro-4-fIuoro-N-[cis-4-(5-methyl-4-methylamino-pyrimidin-2-yIamino)-
cyclohexyl]-benzamide;
4-chloro-N-[cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
3-fluoro-benzamide;
3-chloro-N-[cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyclohexyl]-
5-fluoro-benzamide;
N-[cis-4-(4-dimethyIamino-5-methyl-pyrimidin-2-yIamino)-cyC1-5hexyl]-3,4,5-
trifluoro-benzamide;
N-[cis-4-(4-dimethylamino-5-methyl-pyrimidin-2-ylamino)-cyC1-5hexyl]-3,5-
difluoro-benzamide; and
2-(3,4-difluoro-phenyl)-N-[cis-4-(4-dimethylamino-5-methyI-pyrimidin-2-
ylamino)-cyclohexyl]-acetamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
88. The compound according to claim 75 wherein Rj is selected from the group consisting of:
(i) C1-16 alkyl, and
C1-16 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••nitro,
•*C1-5 alkylcarbonylamino,
•*C3-6 cycloalkylcarbonylamino,
••C1-5 alkyl,
••Cj-5 alkyl substituted by halogen,
••C1-5 alkoxy, and

1076
"C1-5 alkoxy substituted by halogen,
(ii) C3-12 cycloalkyl, and
C3-12 cycloalkyl substituted by carbocyclic aryl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•C1-5Oalkyl,
■C1-5O alkyl substituted by halogen,
•C1-9 alkoxy, and
•C1-5 alkylthio,
(iv) heterocyclyl,
L is Formula (XV);
Y is -C(O)NR5-;
R2 is selected from the group consisting of:
-N(R2a)(R2b), wherein R2a is hydrogen or C1-5 alkyl and R2b is C1-5 alkyl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is 3,4-dihydro-l//-isoquinolinyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
89. The compound according to claim 88 wherein R] is selected from the group consisting of:
(i) C1-16 alkyl, and
C1-16 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryi,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:

1077
••halogen,
••nitro,
-C1-5 alkyl,
—C1-5 alkyl substituted by halogen,
—C1-5 alkoxy, and
••C1-5 alkoxy substituted by halogen,
(ii) C3-12 cycloalkyl, and
C3-12 cycloalkyl substituted by carbocyclic aryl,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•C1-5o alkyl,
•Cj-io alkyl substituted by halogen, and
•C1.9 atkoxy;
R2 is selected from the group consisting of:
-N(R2a)(R2b)! wherein R2a is hydrogen or C1-5 alkyl and R?b is Cj.5 alkyl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is 3,4-dihydro-I//-isoquinolinyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
90. The compound according to any one of claims 75, 88, and 89 wherein p is 1 and T is C1-5
alkyl; R3 and R4 are both hydrogen; and A and B are both single bonds; R5 is hydrogen:
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
91. The compound according to claim 1 selected from the group consisting of:

1078
cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}-N-(3-
iodobenzyl)cyclohexanecarboxamide;
cis-N-(2,4-dichlorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-N-(2,5-dichlorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-4- {[4-(dimethyIamino)-6-methylpyrimidin-2-yI]amino} -N-(4-
methyl benzyl )cyc I ohexan ec arboxam i de;
cis-N-(3,5-dichlorobenzyl)-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-N-(3,5-dimethoxybenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino} cyclohexanecarboxamide;
cis-N-(3-chlorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino} cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-[3-
(trifluoromethyl)benzyl]cyclohexanecarboxamide;
cis-N-[3,5-bis(trifluoromethyI)benzyl]-4-{[4-(dimethylamino)-6-methylpyrimidin-
2-yl]amino}cyclohexanecarboxamide;
cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}-N-(3-
methoxybenzyl)cyclohexanecarboxamide;
cis-N-(4-chlorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-N-(3,4-dich]orobenzyl)-4-{[4-(dimethylamino)-6-methylpyriraidin-2-
yl]amino}cyclohexanecarboxamide;
cis-N-(2,5-difIuorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-N-(2,3-difluorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;

1079
cis-N-(4-bromo-2-fluorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-N-(2,4-difluorobenzyI)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}-N-(3-
methylbenzyl)cyclohexanecarboxamide;
cis-4-{[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino}-N-[2-
(trifluoromethoxy)benzyl]cyclohexanecarboxaraide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lR)-l-
phenyl ethyl] eye I ohexanecarboxam ide;
cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-y ljamino} -N-[( 1S)-1 -(4-
methylphenyl)ethyl]cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lR)-l-(4-
fluoropheny I)ethy 1] cy c lohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lS)-l-(4-
fluorophenyl)ethyl]cyc lohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}-N-[(lR)-l-(3-
methoxyphenyl)ethyl]cyc lohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lS)-l-(3-
methoxyphenyl)ethyl] eye lohexanecarboxamide;
cis-4- {[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino} -N-[( 1S)-1 -(4-
methoxyphenyl)ethyl]cyclohexanecarboxamide;
cis-N-[(lR)-l-(4-chlorophenyI)ethyl]-4-{[4-(dimethylamino)-5-methylpyrimidin-
2-yI]amino} cyclohexanecarboxamide;
cis-N-[l-(4-bromophenyI)ethyl]-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lR)-l-(4-
nitrophenyl)ethyl] cyclohexanecarboxamide;

1080
cis-4- {[4-(dimethy lamino)-5-methy lpyrimidin-2-y ljamino} -N-[( 1S)-1 -(4-
nitrophenyl)ethyl]cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5'methylpyrimidin-2-yl]amino}-N-(3-
fluorophenyl)cyclohexanecarboxamide;
cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yI]amino}-N-(3-
methoxyphenyl)cyclohexanecarboxamide;
cis-N-(3-chIorophenyl)-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lS,2R)-2-
phenylcyclopropyl]cyclohexanecarboxamide;
cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-N-[4-
(trifluoromethyl)phenyl]cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-6-methylpyrimidin"2-yl]amino}-N-[(lR)-l-(3-
methoxyphenyl)ethyl]cyclohexanecarboxamide;
cis-N-[(lS)-l-(4-chIorophenyl)ethy!]-4-{[4-(dimethylamino)-6-methyIpyrimidin-
2-yl]amino}cyclohexanecarboxamide;
cis-N-benzyl-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-4- {[4-(dimethyIamino)-6-methylpyrimidin-2-yl]amino} -N-(4-
fluorobenzyl)cyclohexanecarboxamide;
cis-N-(3,4-difluorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-4- {[4-(dimethyl am ino)-6-methy lpyrimidin-2-y ljamino} -N-[( 1S)-1 -(4-
methoxyphenyl)ethyl]cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-[(lS)-l-(3-
methoxyphenyl)ethyl]cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-[(lR)-l-(4-
fluorophenyl)ethyl]cyclohexanecarboxamide;

1081
cis-N-[( 1R)-1 ~(4-chlorophenyl)ethyI]-4- {[4-(dimethylamino)-6-methy lpyrimidin-
2-yl]amino}cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[( 1 S)-l -(1 -
naphthyl)ethyl]cyclohexanecarboxamide;
cis-N-[(lR)-l-(4-bromophenyl)ethyl]-4-{[4~(dimethylamino)-5-methylpyrimidin-
2-yl]amino}cyclohexanecarboxamide;
cis-N-[(lS)-l-(4-bromophenyl)ethyl]-4-{[4-(dimethylamino)-5-methylpyrimidin-
2 -y I ] am ino} eye Iohexanec arboxam id e;
cis-4- {[4-( dimethyl am ino)-5-methylpyrim id in-2-y ljamino} -N- {(1S)-1 -[4-
(trifluoromethoxy)phenyl]ethyl}cyclohexanecarboxamide;
cis-4-{ [4-(dimethylamino)-5-methy lpyrimidin-2-yl]amino} -N-[( 1R)-1 -(2-
fluorophenyl)ethyl]cyclohexanecarboxamide;
cis-N-{(lS)-l-[3,5-bis(trifluoromethyl)phenyl]ethyI}-4-{[4-(dimethyIamino)-5-
methy!pyrimidin-2-yI]amino}cyclohexanecarboxamide;
4-{[4-(dimethylarnino)-5-methylpyrimidin-2-yl]amino}-N-{(lS)-l-[3-
(trifluoromethyl)phenyl]ethyl}cyclohexanecarboxamide;
4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-{(lS)-l-[2-
(trifluoromethyl)phenyl] ethyl} cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-{(IR)-l-[4-
(trifluoromethoxy)phenyl]ethyl}cyclohexanecarboxamide;
cis-N-[(lS)-l-(4-chlorophenyl)ethyl]-4-{[4-(dimethylamino)-5-methylpyrimidin-
2-yl]amino} cyclohexanecarboxamide;
cis-N-[(lR)-l-(4-chlorophenyl)ethyl]-4-{[4-(dimethylamino)-5-methylpyrimidin-
2-yl]amino}cyclohexanecarboxatnide;
cis-N-[ 1 -(4-chlorophenyl)-1 -methyIethyl]-4- {[4-(dimethy lamino)-5-
methylpyrimidin-2-yl]amino}cyclohexanecarboxamide; and
cis-N- {1 -[3,5-bis(trifluoromethyl)phenyl]-1 -methylethyl} -4-{ [4-(dimethylamino)-
5-methyIpyrimidin-2-yl]amino}cyclohexanecarboxamide;

1082
or a pharmaceuticalIy acceptable salt, hydrate, or solvate thereof.
92. The compound according to claim 1 selected from the group consisting of:
cis-4-{[4-(dimethyiamino)-6-methylpyrimidin-2-yl]amino}-N-(3-
i odobenzy 1 )cyc lohexanecarboxam ide;
cis-N-(2,4-dichIorobenzyI)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyC1-5hexanecarboxamide;
cis-N-(2,5-dichlorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-(4-
methylbenzyl)cyclohexanecarboxamide;
cis-l\-(3,5-dichlorobenzyI)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yljamino} eye lohexanecarboxam ide;
cis-N-(3,5-dimethoxybenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-N-(3-chlorobenzyi)'4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-N-[3,5-bis(trifiuoromethyl)benzyl]-4-{[4-(dimethylamino)-6-methylpyrimidin-
2-yl]amino}cyclohexanecarboxamide;
ciS"4-{[4-(dimethylamino)-6-methylpyrimidin-2-yl]amino}-N-(3-
methoxy benzy l)cycl ohexanecarboxam id e;
cis-N-(4-chlorobenzyl)-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-N-(3,4-dichIorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-N-(2,5-difluorobenzyl)-4-{[4-(dimethylamino)-6-methyIpyrimidin"2-
yl]amino}cyclohexanecarboxamide;

1083
cis-N-(2,3-difluorobenzyl)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-N-(4-bromo-2-fluorobenzyI)-4-{[4-(dimethylamino)-6-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-N-(2,4-dif!uorobenzyl)-4-{[4-(dimethyIamino)-6-methyIpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}-N-(3-
methylbenzyl)cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-yl]amino}-N-[2-
(trifluoromethoxy)benzyl]cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lS)-l-(4-
methylphenyl)ethyl]cyclohexanecarboxamide;
cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-N-[(lR)-l-(4-
fluorophenyl)ethyl]cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin'2-yl]amino}-N-[(lR)-l-(3-
methoxypheny I)ethy l]cycl ohexan ecarboxamide;
cis-4-{[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino}-N-[(lS)-l-(3-
methoxypheny l)ethy ljcyc 1 ohexanecarboxam ide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}~N-[(lS)-l-(4-
methoxyphenyl)ethyl]cyclohexanecarboxamide;
cis-N-[(lR)-l-(4-chlorophenyl)ethyl]-4-{[4-(dimethylamino)-5-methylpyrimidin-
2-yl]amino}cyC1-5hexanecarboxamide;
cis-N-[l-(4-bromophenyI)ethyI]-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-4-{[4-(dimethyIamino)-5-methy]pyrimidin-2-yl]amino}-N-[(lR)-l-(4-
nitrophenyl)ethyl]cyclohexanecarboxamide;
cis-4- {[4-(dimethy lamino)-5-methy lpyrimidin-2-yl]amino} -N-(3 -
m eth oxyph eny l)cyc 1 ohexanecarboxam ide;

1084
cis-N-(3-chlorophenyl)-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-4- {[4-(dimethylamino)-5-methy lpyrimidin-2-y ljamino} -N-[( 1 S,2R)-2-
phenylcyclopropyljcyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-[4-
(trifluoromethyl)phenyl]cyclohexanecarboxamide;
cis-N-[(lS)-l-(4-chlorophenyl)ethyl]-4-{[4-(dimethylamino)-6-methylpyrimidin-
2-yI]amino}cyclohexanecarboxamide;
cis-N-(3,4-difluorobenzyl)-4-{[4-(dimethylamino)-6-methyIpyrimidin-2-
yl]amino}cyclohexanecarboxamide;
cis-4- {[4-(dimethylamino)-6-methylpyrimidin-2-y ljamino} -N-[( 1S)-1 -(4-
methoxyphenyl)ethyl]cyclohexanecarboxamide;
cis-4-{[4-(dimethylamino)-6-methylpyrimidin-2-yI]amino}-N-[(lS)-l-(3-
methoxyphenyl)ethyl]cyclohexanecarboxamide;
cis-N-[( 1R)-1 -(4-chlorophenyI)ethyl]-4-{ [4-(dimethy lamino)-6-methylpyrimidin-
2-yl]amino}cyclohexanecarboxamide;
cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}-N-[(lS)-l-(l-
naphthy l)ethy 1] eye lohexanec arboxam ide;
cis-N-[(lS)-l-(4-bromophenyl)ethyI]-4-{[4-(dimethylamino)-5-methylpyrimidin-
2-yl]amino}cyC1-5hexanecarboxamide;
cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-{(lS)-l-[4-
(trifluoromethoxy)phenyl]ethyl}cyclohexanecarboxamide;
cis-4-{[4-(diraethylamino)-5-methylpyrimidin-2-yl]amino}-N-[(lR)-I-(2-
fluorophenyl)ethyl]cyclohexanecarboxamide;
cis-N-{(lS)-l-[3,5-bis(trifluoromethyI)phenyl]ethyl}-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexanecarboxamide;
4-{[4-(dimethylamino)-5-methy]pyrimidin-2-yI]amino}-N-{(lS)-l-[3-
(trifluoromethyl)phenyl]ethyl}cyclohexanecarboxamide;

1085
4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}-N-{(lS)-l-[2-
(trifluoromethyl)phenyl]ethyl}cyC1-5hexanecarboxamide; and
cis-N-[( 1R)-1 -(4-chlorophenyl)ethyl]-4- {[4-(dimethylamino)-5-methylpyrimidin-
2-yl]amino}cyclohexanecarboxamide;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
93. The compound according to claim 75 wherein R] is selected from the group consisting of:
(i) C1-16 alkyl, and
Ci_i6 alkyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryl,
•carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
••halogen,
••C1-5 alkyl, and
••C1-5 alkyl substituted by halogen,
(i>) C3..12 cycloalkyl, and
C3-12 cycloalkyl substituted by substituent(s) independently selected from
the group consisting of:
•carbocyclic aryl, and
•carbocyclic aryl substituted by halogen,
(iii) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•C1-50 alkyl,
•Ci-io alkyl substituted by halogen,
•C]-9 alkoxy,

1086
•Ci-9 alkoxy substituted by substituent(s) independently selected from the
group consisting of:
••halogen, and
••carbocyclic aryl,
L is Formula (VII);
Y is -C(O)NR5-;
R2 is -N(R2a)(R2b) wherein R2a is hydrogen or C1-5 alkyl and R2b is Cj.5 alkyl;
wherein carbocyclic aryl is phenyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
94. The compound according to claim 75 or 93 wherein p is 1 or 2 and each T is independently
C1-5 alkyl; R3 is hydrogen; R4 is hydrogen or C1-5 alkyl; A and B are both single bonds; R5
is hydrogen; or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
95. The compound according to claim 1 selected from the group consisting of:
N-(3,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-
2-yl]amino} cyclohexyl)urea;
N-(3-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yI]amino}cyclohexyl)-N-methylurea;
N-(3,4-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-N-methylurea;
N'-(cis-4-{[4-(dimethylamino)-5-niethylpyrimidin-2-yl]amino}cyclohexyl)-N-
methy l-N-(3 -methy Ipheny l)urea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-
m ethyl -N-(4-methy Ipheny l)urea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-(3-
fluorophenyl)-N-methylurea;

1087
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-(4-
fluorophenyl)-N-methylurea;
N-(4-chlorophenyI)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyI)-N-methyIurea;
N-(3,4-difluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-N-methylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-N-(3-
methoxyphenyl)-N-methylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyC1-5hexyl)-N-(4-
methoxypheny 1)-N -methy 1 urea;
N-{l-[3,5-bis(trifluoromethyl)phenyl]-l-methylethyl}-N'-(cis-4-{[4-
(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)urea;
N-[l-(4-chlorophenyl)-l-methylethyl]-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)urea;
N-[l~(4-chIorophenyl)-l-methylethyl]-N'-(cis-4-{[4-(dimethylamino)-6-
methylpyrimidin-2-yl]amino}cyclohexyl)urea;
N-[l-(4-chlorophenyl)-l-methytethyl]-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyC1-5hexyl)-N-methylurea;
N-[ 1 -(4-chIorophenyl)-l -methylethyl]-N'-(cis-4- {[4-(dimethylamino)-6-
methylpyrimidin-2-yl]amino}cyclohexyl)-N-methylurea;
N-[l-(4-chIoropheny!)cyclopropyI]-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)-N-methylurea;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N'-(2-
methoxyphenyl)urea;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-N'-(3-
methoxyphenyl)urea;
N-(3,4-dimethoxypheny l)-N'-(cis-4- {[4-(dimethy lamino)-5-methylpyrimidin-2-
y l]amino} cyclohexyl)urea;

1088
N-(cis-4- {[4-(dimethylamino)-5-methyIpyrimidin-2-yl]amino} cyclohexy l)-N'-(4-
fluorophenyl)urea;
N-(3,4-difluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methy]pyrimidin-2-
yf]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N'-[2-
(tri fluoromethoxy )phenyl] u rea;
N-(4-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino} cyclohexyl)urea;
N-[3,5-bis(trifIuoromethyl)phenyI]-N'-(cis-4-{[4-(dimethylamino)-5-
methyIpyrimidin-2-yl]amino}cyclohexyl)urea;
N-(4-bromophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N'-(2-
methylphenyl)urea;
N-benzyl-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino} cyclohexy l)urea;
N-[2-chloro-6-(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyc!ohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N'-
(2,4,6-trichloropheny 1 )urea;
N-(2,4-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyI)-N-methylurea;
N'-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-
methy 1-N - [2 -(tr i fl uoromethoxy )pheny 1] urea;
N-(4-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-N-ethylurea;
N-[3,5-bis(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)-N-ethylurea;

1089
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-(2-
fluorophenyl)-N-methylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yI]amino}cyclohexyl)-N-
ethy 1 -N - [2 -(tr i fluorometh oxy)pheny 1 ] urea;
N'-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-
ethyl-N-phenylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-
ethyl-N-(3-methylphenyl)urea; and
l-(2,3-dichloro-phenyl)-3-[cis-4-(4-dimethyIamino-5-methyl-pyrimidin-2-
ylamino)-cyclohexylmethyl]-urea;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
96. The compound according to claim 1 selected from the group consisting of:
N-(3,4-dimethoxyphenyl)-N'-(cis-4-{[4-(dimethylamino)-5,6-dimethylpyrimidin-
2-yl]amino}cyclohexyl)urea;
N-(3-chlorophenyI)-N'-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-N-methylurea;
N~(3,4-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyC1-5hexyl)-N-methylurea;
N'-(cis-4-{[4-(dimethyIamino)-5-methyIpyrimidin-2-yl]amino}cyC1-5hexyl)-N-
methyl-N-(3-methylphenyl)urea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-
methyl-N-(4-methylphenyl)urea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-(3-
fIuorophenyl)-N-methylurea;
N'-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-N-(4-
fluorophenyl)-N-methylurea;

1090
N-(4-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yI]amino}cyclohexyl)-N-methylurea;
N-(3,4-difluorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yI]amino}cyclohexyl)-N-methylurea;
N'-(cis-4-{[4-(dimethyIamino)-5-methylpyrimidin-2-yl]amino}cyclohexyI)-N-(3-
methoxyphenyI)-N-methylurea;
N'-(cis-4-{[4-(ditnethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-(4-
methoxyphenyl)-N-methylurea;
N-[l-(4-chlorophenyl)-l-methylethyl]-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)urea;
N-[ 1 -(4-chlorophenyl)-1 -methylethyl]-N'-(cis-4-{ [4-(dimethylamino)-6-
methy lpyrim i di n-2 -y 1] amino } cy c lohexy l)urea;
N-[ 1 -(4-chlorophenyl)-1 -methyIethyl]-N'-(cis-4- {[4-(dimethy lamino)-5-
methylpyrimidin-2-yl]amino}cyclohexy!)-N-methylurea;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N'-(4-
fluoropheny 1 )urea;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N'-[2-
(trifluoromethoxy)phenyl]urea;
N-(4-bromophenyl)-N'-(cis-4-{[4-(dirnethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)urea;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N'-(2-
methylphenyl)urea;
N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N'-
(2,4,6-trichlorophenyI)urea;
N-(2,4-dichlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-N-methylurea;
Nl-(cis-4~{[4-(dimethylamino)-5-methylpyrimidin-2-yl]araino}cyclohexyl)-N-
methyl-N-[2-(trifluoromethoxy)phenyl]urea;

1091
N-(4-chlorophenyl)-N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)-N-ethylurea;
N-[3,5-bis(trifluoromethyl)phenyl]-N'-(cis-4-{[4-(dimethylamino)-5-
methylpyrimidin-2-yl]amino}cyclohexyl)-N-ethylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-
ethyl-N-phenylurea;
N'-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-yl]amino}cyclohexyl)-N-
ethyl-N-(3-methyIphenyl)urea; and
l-(2,3-dichloro-phenyl)-3-[cis-4-(4-dimethylamino-5-methyI-pyrimidin-2-
ylamino)-cyclohexylmethyl]-urea;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
97. The compound according to claim 75 wherein Ri is selected from the group consisting of:
heterocyclyl, and
heterocyclyl substituted by substituent(s) independently selected from the
group consisting of:
•carbocyclic aryloxy,
•carbocyclic aryloxy substituted by substituent(s) independently selected
from the group consisting of:
••halogen, and
••C1-5 alkoxy,
L is Formula (X) or (XI);
Y is -C(O)-;
R2 is -N(R2a)(R2b) wherein R2a is C1-5 alkyl and R2b is C1-5 alkyl;
wherein carbocyclic aryl is phenyl;
heterocyclyl is pyridyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.

1092
98. The compound according to claim 75 or 97 wherein p is 1 and T is C1-5 alkyl; R3 and R4 are
both hydrogen; A is a single bond and B is -CH2-;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
99. The compound according to claim 75 wherein Ri is selected from the group consisting of:
(i) carbocyclic aryl, and
carbocyclic aryl substituted by substituent(s) independently selected from
the group consisting of:
•halogen,
•C1-5O alkyl, and
•Ci-10 alkyl substituted by halogen,
(ii) heterocyclyl,
L is Formula (VII); and
Y is -S(O)2-;
R2 is -N(R2a)(R2b) wherein R2a is C;_5 alkyl and R2b is C1-5 alkyl;
wherein carbocyclic aryl is phenyl or naphthyl;
heterocyclyl is furyl; and
halogen is fluoro, chloro, bromo, or iodo;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
100. The compound according to any one of claims 75 or 99 wherein p is 1 and T is C1-5 alkyl;
R3 and R4 are both hydrogen, and A and B are both single bonds;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
101. The compound according to claim 1 is:
4-chloro-N-(cis-4-{[4-(dimethylamino)-5-methylpyrimidin-2-
yl]amino}cyclohexyl)benzenesulfonamide;

1093
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
102. The compound according to claim 1 wherein Ri is selected from hydrogen, -CO2'Bu, or
-CO2Bn (Bn is a benzyl group);
R.2 is selected from the group consisting of:
hydrogen, halogen, hydroxy, carboxy, carbamoyl, amino, C1-5 alkyl, C1-5
alkyl substituted by halogen, C1-5 alkyl substituted by hydroxy, C1-5 alkyl
substituted by carboxy, C1-5 alkyl substituted by carbamoyl, C1-5 alkoxy, C1-5
alkoxy substituted by halogen, -N(R2a)(R2b);
wherein R2a is hydrogen or C1-5 alkyl and R2b is C1-5 alkyl, C3-6 cycloalkyl, or C1-5
alkyl substituted by substituent(s) independently selected from the group
consisting of:
•halogen,
•hydroxy,
•carboxy,
•carbamoyl,
•C1-5 alkoxy,
•amino, and
•C3-6 cycloalkyl;
or R2 is methylamino or dimethylamino when Q is Formula (II);
Each T is independently selected from the group consisting of halogen, hydroxy,
carboxy, carbamoyl, amino, cyano, nitro, C1-5 alkyl, C1-5 alkyl substituted by
halogen, C1-5 alkyl substituted by hydroxy, C1-5 alkyl substituted by carboxy, C1-5
alkyl substituted by carbamoyl, C2.5 alkenyl, C2-5 alkynyl, C3-6 cycloalkyl, C1-5
alkoxy, C1-5 alkoxy substituted by halogen, carbocyclic aryl, heterocyclyl, and
-N(R2a)(R2b);
pisO, 1,2, 3, 4 or 5;

1094
L is selected from the group consisting of Formula (VII), (X), (XI), (XV), (XVIII),
or (XIX): wherein R3 and R4 are independently hydrogen or C,_5 alkyl; and A and
B are independently a single bond or -CH2-; and
*
Y is a single bond;
or a pharmaceutically acceptable salt, hydrate, or solvate thereof.
103. A pharmaceutical composition comprising a therapeutically effective amount of a
compound according to any one of claims 1 to 102 in combination with a pharmaceutically
acceptable carrier.

1095
a pharmaceutical composition according to claim 103.
104 A compound according to any one of claims 1 to 102 or a pharmaceutical composition
according to claim 103 for use in a method of treatment of the human or animal body by
therapy.
105 A compound according to any one of claims 1 to 102 or a pharmaceutical composition
according to claim 103 for use in a method of prophylaxis or treatment of an eating
disorder, obesity or an obesity related disorder of the human or animal body by therapy.
106 A compound according to any one of claims 1 to 102 or a pharmaceutical composition
according to claim 103 for use in a method of prophylaxis or treatment of anxiety,
depression, schizophrenia, addiction, or epilepsy of the human or animal body by therapy.
107 A compound according to any one of claims 1 to 102 for the manufacture of a medicament
for use in the prophylaxis or treatment of an eating disorder, obesity or obesity related
disorders.
108 A compound according to any one of claims 1 to 102 for the manufacture of a medicament
for use in the prophylaxis or treatment of anxiety, depression, schizophrenia, addiction, or
epilepsy.
109 A method of producing a pharmaceutical composition comprising admixing a compound
according to any one of claims 1 to 102 and a pharmaceutically acceptable carrier.


The present invention relates to novel componends of the Formula (1) which act as MCH
receptor antagonists. These compositions are useful in pharmaceutical composition whose use in
cludes prophylaxis or treatment of improving memory function sleeping and arousal anxiety depress-
sion mood disorders seizure, abesity, diabetes, appetite and eating discorders, cardiovascular disease
hypertension, dyslipidemia , myocardial, infarction, binge eating discorders including bulirmia, anorexia,
mental discorders including manic depression, schizophrenia, delirium, dementia, stress, cognitive disorders, attention deficit disor-
der, substance abuse discorders and dyskinesias including Parkinson’s disease, epilepsy, and addiction.

Documents:

01805-kolnp-2005-description provisional.pdf

01805-kolnp-2005-form 1.pdf

01805-kolnp-2005-form 2.pdf

01805-kolnp-2005-form 3.pdf

01805-kolnp-2005-form 5.pdf

01805-kolnp-2005-international publication.pdf

1805-kolnp-2005-granted-abstract.pdf

1805-kolnp-2005-granted-claims.pdf

1805-kolnp-2005-granted-description (complete).pdf

1805-kolnp-2005-granted-examination report.pdf

1805-kolnp-2005-granted-form 1.pdf

1805-kolnp-2005-granted-form 18.pdf

1805-kolnp-2005-granted-form 2.pdf

1805-kolnp-2005-granted-form 26.pdf

1805-kolnp-2005-granted-form 3.pdf

1805-kolnp-2005-granted-form 5.pdf

1805-kolnp-2005-granted-reply to examination report.pdf

abstract-01805-kolnp-2005.jpg


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Patent Number 225639
Indian Patent Application Number 01805/KOLNP/2005
PG Journal Number 47/2008
Publication Date 21-Nov-2008
Grant Date 19-Nov-2008
Date of Filing 12-Sep-2005
Name of Patentee TAISHO PHARMACEUTICAL CO. LTD.
Applicant Address 24-1, TAKADA-3-CHOME, TOSHIMA-KU, TOKYO, JAPAN
Inventors:
# Inventor's Name Inventor's Address
1 YOSHINORI SEKIGUCHI C/O TAISHO PHARMACEUTICAL CO., LTD., OF 24-1, TAKATA-3-CHOME, TOSHIMA-KU, TOKYO, JAPAN
2 KOSUKE KANUMA C/O TAISHO PHARMACEUTICAL CO., LTD., OF 24-1, TAKATA-3-CHOME, TOSHIMA-KU, TOKYO, JAPAN
3 KATSUNORI OMODERA C/O TAISHO PHARMACEUTICAL CO., LTD., OF 24-1, TAKATA-3-CHOME, TOSHIMA-KU, TOKYO, JAPAN
4 TSUYOSHI BUSUJIMA C/O TAISHO PHARMACEUTICAL CO., LTD., OF 24-1, TAKATA-3-CHOME, TOSHIMA-KU, TOKYO, JAPAN
5 THUY-ANH TRAN 4833 FAIRPORT WAY, SAN DIEGO, CA 92130, U.S.A.
6 SANGDON HAN 9953 FIELDTHORN STREET, SAN DIEGO, CA 92127, U.S.A.
7 MARTIN CASPER 6341 PEACH WAY, SAN DIEGO, CA 92130, U.S.A.
8 BRAYN A. KRAMER 8863 DUNCAN ROAD, SAN DIEGO, CA 92126, U.S.A.
9 GRAEME SEMPLE 15920 CAMINO CORDORNIZ, SAN DIEGO, CA 92127, U.S.A.
10 NING ZOU 9829 FIELDTHORN ST., SAN DIEGO, CA 92127, U.S.A.
PCT International Classification Number C07D 215/42; C07D 239/94
PCT International Application Number PCT/JP2004/004624
PCT International Filing date 2004-03-31
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 60/495911 2003-08-19 U.S.A.
2 60/510186 2003-10-09 U.S.A.
3 60/458530 2003-03-31 U.S.A.
4 50/530360 2003-12-16 U.S.A.