[ CAS No. 61367-07-5 ] {[proInfo.proName]}

Name: 61367-07-5|Methyl trans-4-aminocyclohexanecarboxylate hydrochloride|97%
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SKU: A109857
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Quality Control of [ 61367-07-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 61367-07-5 ]

Product Details of [ 61367-07-5 ]

CAS No. :	61367-07-5	MDL No. :	MFCD08274538
Formula :	C₈H₁₆ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NHAYDXCUCXRAMF-UHFFFAOYSA-N
M.W :	193.67	Pubchem ID :	18521575
Synonyms :

Calculated chemistry of [ 61367-07-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.88
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	49.41
TPSA :	52.32 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.21
Log Po/w (WLOGP) :	1.48
Log Po/w (MLOGP) :	1.0
Log Po/w (SILICOS-IT) :	0.65
Consensus Log Po/w :	0.87

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.67
Solubility :	4.13 mg/ml ; 0.0213 mol/l
Class :	Very soluble
Log S (Ali) :	-1.91
Solubility :	2.41 mg/ml ; 0.0124 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.79
Solubility :	31.4 mg/ml ; 0.162 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.4

Safety of [ 61367-07-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 61367-07-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 61367-07-5 ]
Downstream synthetic route of [ 61367-07-5 ]

[ 61367-07-5 ] Synthesis Path-Upstream 1~3

1
[ 67-56-1 ]
[ 1776-53-0 ]
[ 61367-07-5 ]

Yield	Reaction Conditions	Operation in experiment
96.1%	at -10℃; for 1.5 h; Reflux	Example 33; Trans-4-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-l-yl)pyrazoloπ,5-alpyrimidine-3- carboxamido)cyclohexanecarboxylic acid; Step A: Preparation of (trans)-methyl 4-aminocyclohexanecarboxylate hydrochloride.; (Trans)-4-aminocyclohexanecarboxylic acid (200 mg, 1.40 mmol) was suspended in MeOH (5.5 mL) and cooled to -10 ⁰C. To this was added SOCl₂ (204 μL, 2.79 mmol) dropwise and the mixture stirred for 15 minutes. The reaction mixture was warmed to ambient temperature for 15 minutes, followed by heating at reflux for 1 hour. After cooling, the mixture was concentrated to afford the title compound (260 mg, 96.1 percent yield). MS (apci) m/z = 158.0 (M+H).

Reference： [1] Patent: WO2011/6074, 2011, A1, . Location in patent: Page/Page column 95

2
[ 146307-51-9 ]
[ 61367-07-5 ]

Reference： [1] Patent: EP1582521, 2005, A1, . Location in patent: Page/Page column 117
[2] Patent: EP1772454, 2007, A1, . Location in patent: Page/Page column 56

3
[ 61367-07-5 ]
[ 34619-03-9 ]
[ 146307-51-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1 h;	Step 1 trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate To a suspension of trans-methyl 4-aminocyclohexanecarboxylate hydrochloride (1.5 g, 7.7 mmol) in DCM (80 mL) was added DIEA (4 g, 31mmol) and (Boc)₂0 (3 g, 13.9 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuum to give crude product. The crude product was purified by silica gel chromatography (PE / EtOAc = 8 : 1 to 3 : 1) to give trans-methyl 4-((iert-butoxycarbonyl)amino)cyclohexanecarboxylate (1.7 g, yield 86percent) as a white solid. 1H NMR (400 MHz, Methanol-d4) δ 4.38 (br, 1H), 3.66 (s, 3H), 3.47- 3.40 (m, 1H), 2.22-2.19 (m, 1H), 2.07-1.98 (m, 4H), 1.56-1.50 (m, 2H), 1.43 (s, 9H), 1.15-1.12 (m, 2H).

Reference： [1] Patent: WO2015/188051, 2015, A1, . Location in patent: Page/Page column 139

[ 61367-07-5 ] Synthesis Path-Downstream 1~87

1
[ 61367-07-5 ]
[ 503-66-2 ]
[ 727736-49-4 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); water; at 0 - 20℃; for 20h;	(1) To a solution of <strong>[61367-07-5]methyl trans-4-aminocyclohexanecarboxylate hydrochloride</strong> (1.0 g) obtained in Reference Example 2(1), triethylamine (1.1 ml), 30 % aqueous 3-hydroxypropionic acid solution (1.86 ml) in N,N-dimethylformamide (15 ml) are added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.19 g) and 1-hydroxybenzotriazole (837 mg) under ice-cooling. The mixture is then stirred at room temperature for 20 hours. The reaction solution is concentrated and saturated aqueous sodium hydrogen carbonate solution is poured to the residue, followed by extraction with chloroform. The organic layer is dried over sodium sulfate and evaporated to remove the solvent. The resulting residue is purified by silica gel column chromatography (eluent : ethyl acetate)to give methyl trans-4-[(3-hydroxypropanoyl)amino]cyclohexanecarboxylate (534 mg). APCI-MS M/Z : 230[M+H]+.

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 127

2
[ 110-91-8 ]
[ 61367-07-5 ]
[ 412293-70-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In chloroform; at 0 - 20℃; for 19h;	(1) Trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (800 mg) obtained in Reference Example 1(2) is dissolved in chloroform (30 ml), and thereto are added morpholine (560 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.24 g) and triethylamine (650 mg) under ice-cooling. The mixture is then stirred at room temperature for 19 hours. Ice-water is poured to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed with 10 % hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine successively and dried over sodium sulfate. The solvent is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent : chloroform, followed by chloroform/methanol = 30/1) to give methyl trans-4-(morpholin-4-ylcarbonyl)-cyclohexanecarboxylate (897 mg). APCI-MS M/Z:256[M+H]+.

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 147

3
[ 123-75-1 ]
[ 61367-07-5 ]
[ 727737-09-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In chloroform; at 0 - 20℃; for 17h;	(1) Trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (20.0 g) obtained in Reference Example 1(2) is dissolved in chloroform (200 ml), and thereto are added pyrrolidine (9.2 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (24.7 g) and triethylamine (13.6 g) under ice-cooling. The mixture is then stirred at room temperature for 17 hours. Ice-water is poured to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed with 10 % hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine successively, and dried over sodium sulfate. The solvent is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent : chloroform, followed by chloroform/methanol = 20/1) to give methyl trans-4-(pyrrolidin-1-ylcarbonyl)-cyclohexanecarboxylate (11.8 g). APCI-MS M/Z:240[M+H]+.

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 146-147

4
[ 89711-08-0 ]
[ 61367-07-5 ]
[ 727736-96-1 ]

Yield	Reaction Conditions	Operation in experiment
		(1) Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (1.22 g) obtained in Reference Example 2(1) is suspended in dichloromethane (10 ml), and thereto is added triethylamine (1.76 ml) and the mixture is stirred for several minutes. After a solution of t-butyl (2-oxoethyl)carbamate (1.00 g) in dichloromethane (5 ml) and sodium triacetoxy borohydride (1.46 g) are added successively under ice-cooling, the reaction solution is warmed to the room temperature and stirred for 15 hours. Saturated aqueous sodium hydrogen carbonate solution is poured to the reaction solution, and the mixture is extracted with chloroform. The organic layer is dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. A portion (1.71 g) of the resulting residue (2.33 g) is purified by silica gel column chromatography (eluent: chloroform/methanol = 10/1) to give methyl trans-4-({2-[(t-butoxycarbonyl)amino]ethyl}amino)-cyclohexanecarboxylate (793 mg). APCI-MS M/Z:301[M+H]+.

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 142

5
[ 61367-07-5 ]
[ 111-44-4 ]
[ 609805-47-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; sodium iodide; In tetrahydrofuran; N,N-dimethyl acetamide; for 24h;Heating / reflux;	(1) Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (47.5 g) obtained in Reference Example 2(1), bis(2-chloroethyl)ether (34.5 ml), sodium carbonate (77.9 g) and sodium iodide (88 g) are suspended in a mixture of tetrahydrofuran (1400 ml) and N,N-dimethylacetamide (280 ml). The mixture is then heated under reflux for 18 hours. Bis(2-chloroethyl)ether (23 ml) and sodium iodide (22 g) are added to the reaction solution and the mixture is refluxed for additional 6 hours. The reaction solution is concentrated under reduced pressure. The residue is dissolved in ethyl acetate/water and the organic layer is separated. The organic layer is washed with water and saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate/hexane = 1/30, subsequently by ethyl acetate/hexane = 1/5 followed by 1/3) to give methyl trans-4-morpholin-4-ylcyclohexane-carboxylate (53.9 g). APCI-MS M/Z:228[M+H]+.

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 123

6
[ 506-59-2 ]
[ 61367-07-5 ]
[ 727737-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In chloroform; at 0 - 20℃; for 17h;	(1) Trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (20.0 g) obtained in Reference Example 1(2) is dissolved in chloroform (200 ml), and thereto are added dimethylamine hydrochloride (10.5 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (24.7 g) and triethylamine (26.0 g) under ice-cooling. The mixture is then stirred at room temperature for 17 hours. Ice-water is poured to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed with 10 % hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine successively and dried over sodium sulfate. The solvent is concentrated under reduced pressure and the resulting residue is purified by silica gel column chromatography (eluent: chloroform, followed by chloroform/methanol = 20/1) to give methyl trans-4-[(dimethylamino)carbonyl]-cyclohexanecarboxylate (20.1 g). APCI-MS M/Z:214[M+H]+.

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 146

7
[ 79-14-1 ]
[ 61367-07-5 ]
[ 727736-47-2 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 20h;	(1) 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (742 mg) and 1-hydroxybenzotriazole (523 mg) are added to a solution of <strong>[61367-07-5]methyl trans-4-aminocyclohexanecarboxylate hydrochloride</strong> (500 mg) obtained in Reference Example 2(1), triethylamine (540 mul) and glycolic acid (295 mg) in N,N-dimethylformamide (10 ml) under ice-cooling.

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 126-127

8
[ 61367-07-5 ]
[ 4635-59-0 ]
[ 609805-37-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃; for 3h;	(2) Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (45.31 g) obtained in (1) above is suspended in dichloromethane (1000 ml), and thereto is added 4-chlorobutyryl chloride (31.5 ml) under ice-cooling, followed by dropwise addition of a solution of triethylamine (81.5 ml) in dichloromethane (80 ml). The reaction solution is warmed to room temperature, stirred for 3 hours and concentrated under reduced pressure. To the resulting residue are poured ethyl acetate and 5 % hydrochloric acid, and the organic layer is separated, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer is dried over sodium sulfate and treated with activated carbon, and the filtrate is concentrated under reduced pressure. The resulting residue is suspended in diisopropyl ether. The precipitates are collected by filtration and dried to give methyl trans-4-[(4-chlorobutanoyl)amino]cyclohexanecarboxylate (38.81 g). APCI-MS M/Z:262/264[M+H]+.

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 117

9
[ 50-00-0 ]
[ 61367-07-5 ]
[ 609805-43-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; sodium acetate;palladium 10% on activated carbon; In methanol; water; at 20℃; under 760.051 Torr; for 3.5h;	(1) Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (93.0 g) obtained in Reference Example 2(1) is dissolved in methanol (1000 ml), and thereto are added 35 % aqueous formaldehyde solution (95.4 ml), sodium acetate (39.4 g) and 10 % palladium/carbon (10 g). The mixture is then stirred at room temperature for 3.5 hours under atmospheric hydrogen pressure. The insoluble materials are removed by filtration, and the filtrate is concentrated under reduced pressure. To the resulting residue is poured 20 % aqueous potassium carbonate solution (500 ml), and the mixture is extracted with chloroform. The organic layer is dried over sodium sulfate and potassium carbonate, and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate = 2/1) to give methyl trans-4-dimethylaminocyclohexanecarboxylate (87.3 g). APCI-MS M/Z:186[M+H]+.;

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 122

10
[ 61367-07-5 ]
[ 93206-09-8 ]
[ 609805-64-3 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 72h;	(2) [(2-Benzyloxy)ethoxy]acetic acid (6.51 g) obtained in (1) above, <strong>[61367-07-5]methyl trans-4-aminocyclohexanecarboxylate hydrochloride</strong> (5.27 g) obtained in Reference Example 2(1) and 1-hydroxybenzotriazole (5.06 g) are dissolved in N,N-dimethylformamide (100 ml). To the mixture are added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (7.10 g) and triethylamine (4.50 ml) successively under ice-cooling, and the mixture is stirred at room temperature for 3 days. The reaction solution is concentrated under reduced pressure, and to the resulting residue is added an aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 1:1 followed by ethyl acetate) to give methyl trans-4-([2-(2-benzyloxy)ethoxy]acetyl}amino)cyclohexanecarboxylate (8.24 g). APCI-MS M/Z:350[M+H]+.

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 119

11
[ 1633-82-5 ]
[ 61367-07-5 ]
[ 727736-51-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In chloroform; at 0 - 20℃; for 2.33333h;	(1) Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (4.08 g) obtained in Reference Example 2(1) is suspended in chloroform (50 ml), and thereto is added triethylamine (8.8 ml) under ice-cooling. Subsequently, a solution of 3-chloropropanesulfonyl chloride (3.35 ml) in chloroform (20 ml) is added dropwise over 20 minutes under the same temperature. After stirring for 2 hours at room temperature, 5 % hydrochloric acid is added to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is suspended in diisopropylamine, and filtered to collect precipitates to give methyl trans-4-[(3-chloropropyl)sulfonyl]amino}cyclohexanecarboxylate (6.14 g). APCI-MS M/Z:315/317[M+H]+.

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 128

12
[ 146307-51-9 ]
[ 61367-07-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In 1,4-dioxane; at 20℃; for 19h;	Reference Example 2;: Trans-4-(2-oxopyrrolidin-1-yl)cyclohexanecarboxylic acid ; [] (1) Methyl trans-4-[(t-butoxycarbonyl)amino]-cyclohexanecarboxylate (234.0 g) obtained in Reference Example 1 is dissolved in dioxane (500 ml), and thereto is added 4 N hydrogen chloride/dioxane (500 ml), and the mixture is stirred at room temperature for 19 hours. The reaction solution is concentrated under reduced pressure, and the resulting residue is suspended in diethyl ether. The precipitates are collected by filtration to give methyl trans-4-aminocyclohexanecarboxylate hydrochloride (121.9 g). APCI-MS M/Z:158[M+H]+.;
	With hydrogenchloride; In 1,4-dioxane; water; at 20℃; for 19h;	(2) To a solution of the compound obtained in the above step (1) (234.0 g) in dioxane (500 mL) was added 4N HCl/dioxane (500 mL) and the mixture was stirred at room temperature for 19 hours. The reaction mixture was concentrated in vacuo and the resultant residue was suspended in diethylether and the precipitates were collected by filtration to give methyl trans-4-aminocyclohexanecarboxylate hydrochloride (121.9 g). MS(APCI)m/z; 158 [M+H]+

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 117
[2]Patent: EP1772454,2007,A1 .Location in patent: Page/Page column 56

13
[ 628-21-7 ]
[ 61367-07-5 ]
[ 609805-45-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In tetrahydrofuran; N,N-dimethyl acetamide; at 70℃; for 20h;	(1) Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (10 g) obtained in Reference Example 2(1), 1,4-diiodobutane (19.2 g) and sodium carbonate (16.4 g) are suspended in a mixture of tetrahydrofuran (300 ml) and N,N-dimethyl acetamide (60 ml), and the mixture is stirred at 70C for 20 hours. The reaction solution is concentrated under reduced pressure. The residue is dissolved in ethyl acetate/water and the organic layer is separated. The organic layer is washed with water and saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate/hexane = 1/5) to give methyl trans-4-pyrrolidin-1-ylcyclohexanecarboxylate (10.9 g). APCI-MS M/Z:212[M+H]+.

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 123

14
[ 61367-07-5 ]
[ 627-11-2 ]
methyl trans-4-[(2-chloroethoxy)carbonyl]amino}cyclohexanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In chloroform; at 0 - 20℃; for 2.5h;	(1) Methyl trans-4-aminocyclohexanecarboxylate hydrochloride (5.00 g) obtained in Reference Example 2(1) is dissolved in chloroform (60 ml), and thereto is added triethylamine (11 ml) under ice-cooling, followed by dropwise addition of a solution of 2-chloroethyl chloroformate (3.3 ml) in chloroform (10 ml). After stirring at room temperature for 2.5 hours, to the reaction solution is added 5 % hydrochloric acid and the mixture is extracted with chloroform. The organic layer is washed with saturated brine, dried over sodium sulfate, and then evaporated to remove the solvent under reduced pressure. The resulting residue is suspended in chloroform/diisopropyl ether. The precipitates are collected by filtration and dried to give methyl trans-4-[(2-chloroethoxy)carbonyl]amino}cyclohexanecarboxylate (5.11 g). APCI-MS M/Z:264/266[M+H]+.

Reference： [1]Patent: EP1582521,2005,A1 .Location in patent: Page/Page column 120

15
[ 104-53-0 ]
[ 61367-07-5 ]
N-[trans-4-(methoxycarbonyl)-cyclohexyl]-N-(3-phenylpropyl)-amine-hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; In methanol;	EXAMPLE XXV N-[trans-4-(methoxycarbonyl)-cyclohexyl]-N-(3-phenylpropyl)-amine-hydrochloride A solution of 2 g of methyl trans-4-aminocyclohexane-carboxylate-hydrochloride, 1.5 ml of 3-phenylpropionaldehyde and 1.3 g of sodium cyanoborohydride in 40 ml of dry methanol is stirred for 20 hours at ambient temperature. The mixture is diluted with water and extracted with ethyl acetate. The combined ethyl acetate phases are dried, acidified with ethereal hydrochloric acid and the solvent is removed under reduced pressure. The residue is triturated with acetone, suction filtered and washed with acetone and then with ether. Yield: 1.9 g (59.1% of theory), Melting point: 258-260 C.

Reference： [1]Patent: US5442064,1995,A

16
[ 150594-36-8 ]
[ 61367-07-5 ]
[ 125700-67-6 ]
[ 80029-43-2 ]
[ 150594-70-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; In N-methyl-acetamide;	EXAMPLE XXIII 6-(4-Cyanophenyl)-4-[[trans-4-(methoxycarbonyl)-cyclohexyl]-aminocarbonyl]-2-[(morpholinocarbonyl)-methyl]-(2H)-pyridazin-3-one A suspension of 1.2 g of 4-carboxy-6-(4-cyanophenyl)-2-[(morpholinocarbonyl)-methyl]-(2H)-pyridazin-3-one, 1.29 g of 2-[(1H)-benzotriazol-1-yl]-1,1,3,3-tetramethyl-uroniumtetrafluoroborate, 0.64 g of trans methyl-4-amino-cyclohexanecarboxylate-hydrochloride, 0.54 g of 1-hydroxy-(1H)-benzotriazole hydrate and 0.81 g of N-methylmorpholine in 100 ml of dimethylformamide is stirred for 16 hours at ambient temperature. The solvent is evaporated off under reduced pressure at a bath temperature of 80 C. and the remaining oil is chromatographed. Yield: 1.38 g (83% of theory), Melting point: 195-200 C. Rf value: 0.63 (silica gel; methylene chloride/methanol=9:1)

Reference： [1]Patent: US5418233,1995,A

17
[ 167757-41-7 ]
[ 61367-07-5 ]
[ 530-62-1 ]
[ 167756-97-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; methanol;	Example 1 5-tert.Butyloxycarbonyl-2-[4-[(trans-4-methoxycarbonyl-cyclohexyl)-aminocarbonyl]-phenyl]-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine 1.11 g of N,N'-carbonyl-diimidazole is added to a suspension of 2.50 g of 5-tert.butyloxycarbonyl-2-(4-carboxy-phenyl]-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine in 50 ml of tetrahydrofuran and the mixture is stirred for 3 hours at ambient temperature. Then a solution of 1.34 g of methyl trans-4-amino-cyclohexanecarboxylate-hydrochloride and 1.0 ml of triethylamine in 10 ml of tetrahydrofuran is added and the mixture is stirred for 5 days at ambient temperature. The solvent is evaporated off and the residue is distributed between water and methylene chloride. The methylene chloride phase is washed with sodium hydrogen carbonate solution and water, then dried and evaporated down. The residue is filtered with methylene chloride/methanol (19:1) over a little silica gel. The filtrate is evaporated down, the solids are triturated with ether and suction filtered. Yield: 2.60 g (75% of theory), Rf value: 0.75 (silica gel; methylene chloride/methanol=9:1) Mass spectrum: M+ =499

Reference： [1]Patent: US5607944,1997,A

18
[ 628-77-3 ]
[ 61367-07-5 ]
[ 733784-92-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In tetrahydrofuran; N,N-dimethyl acetamide; water; ethyl acetate; at 70℃; for 20h;	(3) A suspension of the compound obtained in the above step (2) (10 g), 1,5-diiodopentane (9.2 mL) and sodium carbonate (16.4 g) in tetrahydrofuran (300 mL)/N,N-dimethylacetamide (60 mL) was stirred at 70 C for 20 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate/water. The organic layer was separated and washed successively with water and brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was purified by a column chromatography on NH-silica gel (Solvent; ethyl acetate/n-hexane = 1: 5) to give methyl trans-4-(1-piperidyl)cyclohexanecarboxylate (10.17 g). MS(APCI)m/z; 226 [M+H]+

Reference： [1]Patent: EP1772454,2007,A1 .Location in patent: Page/Page column 56

19
[ 1177416-01-1 ]
[ 61367-07-5 ]
[ 76-05-1 ]
methyl trans-4-((8-(cyclopropylamino)-3-((3-fluoro-4-pyridinyl)carbamoyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexanecarboxylate bis(trifluoroacetate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9.97%		To a suspension of 6-chloro-8-(cyclopropylamino)-N-(3-fluoropyridin-4- yl)imidazo[l,2-b]pyridazine-3-carboxamide (0.030 g, 0.087 mmol) and DIEA (0.227 mL, 1.298 mmol) in NMP (1 mL) was added trans-methyl 4- aminocyclohexanecarboxylate, HCl (0.201 g, 1.038 mmol). The resulting suspension was heated to 120 0C in a 300W CEM Discover microwave for 60 min. The crude <n="63"/>material was diluted with 1 mL MeOH and purified via preparatory HPLC using a YMC ODS C-18 column (30 x 250 mm) 0%-100%B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B = O, final % B = 100, gradient time 240 min, hold at 100% B 40 min, flow rate 25 mL/min. Material was redissolved in DMSO/THF and purified via preparatory HPLC using a YMC ODS C-18 column (30 x 250 mm) 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B = O, final % B = 100, gradient time 60 min, flow rate 25 mL/min, to afford methyl trans-4-((8-(cyclopropylamino)-3-((3-fluoro-4- pyridinyl)carbamoyl)imidazo[l,2-b]pyridazin-6-yl)amino)cyclohexanecarboxylate, 2TFA (0.006 g, 9.97% yield) obtained as a white foam. LC/MS, m/z 468.0 (M+l). HPLC Rt = 4.120 min. YMC S5 ODS-A column (4.6 x 50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.2% H3PO4). Solvent A: (10% MeOH, 90% H2O, 0.2% H3PO4). Gradient, start % B = O, final % B = 100, gradient time 4 min, hold at 100% 1 min, flow rate 4 mL/min. 1H NMR (500 MHz, DMSO-d6) delta ppm11.46 (1 H, s), 8.67 (1 H, d, J=2.75 Hz), 8.55 (1 H, t, J=5.91 Hz), 8.41 (1 H, d, J=5.77 Hz), 8.00 (1 H, s), 7.57 (1 H, s), 7.00 (1 H, s), 6.07 (1 H, s), 2.06 (3 H, s), 1.91 (4 H, s), 1.58 (1 H, d), 1.30 (4 H, d, J=10.45 Hz), 1.05 (2 H, d, J=I 1.27 Hz), 0.76 (2 H, d, J=4.95 Hz), 0.57 - 0.67 (2 H, m).

Reference： [1]Patent: WO2009/100375,2009,A1 .Location in patent: Page/Page column 60-61

20
[ 657-05-6 ]
[ 61367-07-5 ]
[ 1207529-63-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 1.83333h;Inert atmosphere;	Step 1 :Trans-4-(2-Chloro-5-trifluoromethyl-benzoylamino)-cyclohexane carboxylic acid methyl esterTo a stirred suspension of trans-4-amino-cyclohexylcarboxylic acid methyl ester hydrochloride (6.7 g, 34.7 mmol) in dry THF (90 ml) under nitrogen atmosphere was added triethylamine (12 ml, 86.8 mmol). The suspension was cooled to 0C and 2- chloro-5-(trifluoromethyl)benzoyl chloride (8.85 g, 36.4 mmol) in dry THF (40 ml) was added dropwise over 20 minutes. The resulting thick, colourless slurry was stirred at 0-5C for 30 minutes and then allowed to warm to room temp and stirred at RT for 1 hour. The reaction was quenched by the dropwise addition of water (5 ml) in THF (45 ml) to give a clear solution. This was diluted with water (100 mi) and ethyl acetate (300 ml). The biphasic mixture was stirred for 5 minutes then the organic phase was separated and washed successively with water (100 ml), saturated sodium bicarbonate (100 ml) and saturated brine (100ml), dried (MgS04), filtered and evaporated to give a colourless solid.; [M+H]+ 364.

Reference： [1]Patent: WO2011/92293,A1 .Location in patent: Page/Page column 80-81
Patent: ,2011, .Location in patent: Page/Page column 80-81

21
[ 61367-07-5 ]
[ 1319743-48-0 ]

Reference： [1]Patent: WO2011/92293,A1
Patent: ,2011,

22
[ 61367-07-5 ]
[ 1207530-03-7 ]

Reference： [1]Patent: WO2011/92293,A1
Patent: ,2011,

23
[ 61367-07-5 ]
[ 1319742-69-2 ]

Reference： [1]Patent: WO2011/92293,A1
Patent: ,2011,

24
[ 61367-07-5 ]
[ 1319742-71-6 ]

Reference： [1]Patent: WO2011/92293,A1
Patent: ,2011,

25
[ 61367-07-5 ]
[ 1319742-72-7 ]

Reference： [1]Patent: WO2011/92293,A1
Patent: ,2011,

26
[ 61367-07-5 ]
[ 1319742-65-8 ]

Reference： [1]Patent: WO2011/92293,A1
Patent: ,2011,

27
[ 61367-07-5 ]
[ 1207529-70-1 ]

Reference： [1]Patent: WO2011/92293,A1
Patent: ,2011,

28
[ 61367-07-5 ]
[ 1319743-29-7 ]

Reference： [1]Patent: WO2011/92293,A1
Patent: ,2011,

29
[ 61367-07-5 ]
[ 1207529-71-2 ]

Reference： [1]Patent: WO2011/92293,A1
Patent: ,2011,

30
[ 61367-07-5 ]
[ 1319742-68-1 ]

Reference： [1]Patent: WO2011/92293,A1
Patent: ,2011,

31
[ 1289045-10-8 ]
[ 61367-07-5 ]
[ 1344685-36-4 ]

Yield	Reaction Conditions	Operation in experiment
		Methyl trans-4-aminocyclohexanecarboxylate monohydrochloride (10.0 g) was dissolved in ethyl acetate (50 mL), THF (10 ml) and saturated aqueous potassium carbonate solution (20 mL) under ice-cooling, and the mixture was extracted with a mixed solvent of ethyl acetate/THF (5/1). The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a colorless powder (5.98 g). A mixture of the obtained powder (5.98 g), 4-(cyclopropylmethoxy)-2-nitrobenzaldehyde (8.41 g) and toluene (200 mL) was refluxed for 15 hr. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. The residue was dissolved in triethyl phosphite (25.3 g), and the mixture was stirred at 190 C. for 5 hr. The reaction mixture was allowed to cool to room temperature and purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (6.98 g).MS (ESI+): [M+H]+ 329.2

Reference： [1]Patent: US2011/263562,2011,A1 .Location in patent: Page/Page column 80

32
[ 1195972-63-4 ]
[ 61367-07-5 ]
[ 1195972-61-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 20 - 80℃;	Example 27 4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester 1-(2-Chloro-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (300 g), 4-amino-cyclohexanecarboxylic acid ethyl ester HCl salt (155 g), and K2CO3 (170 g) in NMP (2.35 L) were stirred at 80 C. for 5 h and then stirred overnight at room temperature. The reaction mixture was then stirred on an ice bath, and 2.5 L water was slowly added while stirring, and cooling continued until completion of the exothermic reaction. Upon cooling, the mixture was filtered, and resulting solid was rinsed with H2O and dried in vacuo overnight to yield 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester (97%).
97%	With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 20 - 80℃;	Example 14 4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester 1-(2-Chloro-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (300 g), 4-amino-cyclohexanecarboxylic acid ethyl ester HCl salt (155 g), and K2CO3(170 g) in NMP (2.35 L) were stirred at 80 C. for 5 h and then stirred overnight at room temperature. The reaction mixture was then stirred on an ice bath, and 2.5 L water was slowly added while stirring, and cooling continued until completion of the exothermic reaction. Upon cooling, the mixture was filtered, and resulting solid was rinsed with H2O and dried in vacuo overnight to yield 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester (97%).

Reference： [1]Patent: US2011/301170,2011,A1 .Location in patent: Page/Page column 31
[2]Patent: US2011/301171,2011,A1 .Location in patent: Page/Page column 23-24

33
[ 61367-07-5 ]
[ 1357279-12-9 ]

Reference： [1]Patent: US2012/28969,2012,A1

34
[ 61367-07-5 ]
[ 1357279-13-0 ]

Reference： [1]Patent: US2012/28969,2012,A1

35
[ 61367-07-5 ]
[ 1357279-15-2 ]

Reference： [1]Patent: US2012/28969,2012,A1

36
[ 61367-07-5 ]
[ 1357279-14-1 ]

Reference： [1]Patent: US2012/28969,2012,A1

37
[ 61367-07-5 ]
(1r,1r)-4-(2-phenyl-1H-indole-6-sulfonamido)-N-((R)-1-(pyridin-2-yl)ethyl)cyclohexanecarboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: US2012/28969,2012,A1

38
[ 16063-69-7 ]
[ 61367-07-5 ]
[ 1370457-32-1 ]

Yield	Reaction Conditions	Operation in experiment
28%	With caesium carbonate; In N,N-dimethyl-formamide; at 150℃; for 5.5h;sealed tube;	EXAMPLE 133; irans^-iP'-Piperazin-l-yl-e-ipyrazin- -ylaminoJ^^'-bipyridin^- yl]amino}cyclohexanecarboxylic acid; a) Methyl frans-4-[(2,6-dichloropyridin-4-yl)amino]cyclohexanecarboxylate; A mixture of 2,4,6-trichloropyridine (2.22 g, 12.20 mmol), methyl trans-4- aminocyclohexanecarboxylate hydrochloride (2.6 g, 13.42 mmol) and cesium carbonate (6.74 g, 48.8 mmol) in DMF (30 mL) was stirred in a sealed tube at 150 C. After 5.5 hours, the crude was poured on water (30 mL) and EtOAc (30 mL). The aqueous phase was extracted with EtOAc (3x20 mL). The combined organic phases were dried (Na2S04), filtered and concentrated. Purification of the residue by flash chromatography (hexanes/ethyl acetate 15% to 30% ethyl acetate) gave the title compound (1.02 g, 28%) as a yellow solid.LRMS (m/z): 303/305 (M+1)+.1 H N R (250 MHz, CHLOROFORM-d) delta ppm 1.24 (m, 4H), 1.6 (m, 2H), 2.11 (m, 2H), 2.31 (m, 1H), 3.26 (m, 1 H), 3.69 (s, 3H), 4.32 (d, J = 7.3 Hz, 1 H), 6.34 (s, 2H)
28%	With caesium carbonate; In N,N-dimethyl-formamide; at 150℃; for 5.5h;	A mixture of 2,4,6-trichloropyridine (2.22 g, 12.20 mmol), <strong>[61367-07-5]methyl trans-4-aminocyclohexanecarboxylate hydrochloride</strong> (2.6 g, 13.42 mmol) and cesium carbonate (6.74 g, 48.8 mmol) in DMF (30 mL) was stirred in a sealed tube at 150 C. After 5.5 hours, the crude was poured on water (30 mL) and EtOAc (30 mL). The aqueous phase was extracted with EtOAc (3x20 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated. Purification of the residue by flash chromatography (hexanes/ethyl acetate 15% to 30% ethyl acetate) gave the title compound (1.02 g, 28%) as a yellow solid.LRMS (m/z): 303/305 (M+1)+.1 H NMR (250 MHz, CHLOROFORM-d) delta ppm 1.24 (m, 4H), 1.6 (m, 2H), 2.11 (m, 2H), 2.31 (m, 1 H), 3.26 (m, 1 H), 3.69 (s, 3H), 4.32 (d, J = 7.3 Hz, 1 H), 6.34 (s, 2H)

Reference： [1]Patent: WO2012/41476,2012,A1 .Location in patent: Page/Page column 174-175
[2]Patent: EP2441755,2012,A1 .Location in patent: Paragraph 0320

39
[ 16063-69-7 ]
[ 61367-07-5 ]
[ 1370457-33-2 ]

Reference： [1]Patent: WO2012/41476,2012,A1
[2]Patent: EP2441755,2012,A1

40
[ 960061-69-2 ]
[ 61367-07-5 ]
C₅₆H₅₈N₁₄O₁₀S₆ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2376 - 2387

41
[ 1410737-09-5 ]
[ 61367-07-5 ]
[ 1410737-15-3 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	EDCI (19 mg, 0.097 mmol), HOBt (13 mg, 0.097 mmol), and DIEA (0.034 mL, 0.195 mmol) were added to a solution of carboxylic acid intermediate 13 (30 mg, 0.065 mmol) dissolved in DCM. After 10 minutes, <strong>[61367-07-5]methyl trans-4-aminocyclohexanecarboxylate hydrochloride</strong> (25 mg, 0.13 mmol) and a catalytic amount of DMAP were added. After stirring overnight, the solvent was removed and the crude product was purified by column chromatography to give the 30 mg of intermediate 18 as a white solid.

Reference： [1]Patent: US2012/289494,2012,A1 .Location in patent: Page/Page column 74

42
[ 7473-98-5 ]
[ 61367-07-5 ]
C₁₈H₂₅NO₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 4320 - 4342

43
[ 61367-07-5 ]
[ 5368-37-6 ]
[ 1507362-24-4 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 10003 - 10015

44
[ 61367-07-5 ]
[ 5368-37-6 ]
[ 1507362-23-3 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 10003 - 10015

45
[ 61367-07-5 ]
trans-methyl 4-(1-(4-chloro-2-fluorobenzyl)-N-methyl-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-6-carboxamido)cyclohexanecarboxylate [ No CAS ]

Reference： [1]Patent: WO2015/188051,2015,A1

46
[ 61367-07-5 ]
[ 400899-07-2 ]

Reference： [1]Patent: WO2015/188051,2015,A1

47
[ 61367-07-5 ]
[ 146447-21-4 ]

Reference： [1]Patent: WO2015/188051,2015,A1

48
[ 61367-07-5 ]
[ 34619-03-9 ]
[ 146307-51-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 1h;	Step 1 trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate To a suspension of trans-methyl 4-aminocyclohexanecarboxylate hydrochloride (1.5 g, 7.7 mmol) in DCM (80 mL) was added DIEA (4 g, 31mmol) and (Boc)20 (3 g, 13.9 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuum to give crude product. The crude product was purified by silica gel chromatography (PE / EtOAc = 8 : 1 to 3 : 1) to give trans-methyl 4-((iert-butoxycarbonyl)amino)cyclohexanecarboxylate (1.7 g, yield 86%) as a white solid. 1H NMR (400 MHz, Methanol-d4) delta 4.38 (br, 1H), 3.66 (s, 3H), 3.47- 3.40 (m, 1H), 2.22-2.19 (m, 1H), 2.07-1.98 (m, 4H), 1.56-1.50 (m, 2H), 1.43 (s, 9H), 1.15-1.12 (m, 2H).

Reference： [1]Patent: WO2015/188051,2015,A1 .Location in patent: Page/Page column 139

49
[ 1612148-85-2 ]
[ 61367-07-5 ]
trans-4-(5-(2,6-dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazole-3-carboxamido)cyclohexanecarboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3758 - 3770

50
[ 1612148-85-2 ]
[ 61367-07-5 ]
methyl trans-4-(5-(2,6-dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazole-3-carboxamido)cyclohexane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		5-(2,6-Dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazole-3-carboxylic acid (2) (150 mg, 0.438 mmol) was dissolved in THF (7 mL). To the solution was added BOP (193 mg, 0.438 mmol) and triethylamine (0.182 mL, 1.314 mmol). The resulting mixture was stirred at room temperature for 20 min. trans-Methyl-4-aminocyclohexanecarboxylate hydrochloride (93 mg, 0.482 mmol) was added and stirred at room temperature for 2 h. THF was evaporated in vacuo, water was added to the residue and the aqueous layer was extracted with CH2Cl2 (3 * 20 mL). The combined organic layers were washed with water, brine and then dried with Na2SO4 .The solvent was evaporated in vacuo to give the crude residue. The residue was purified by silica gel flash chromatography (EtOAc/Hex) to give trans-methyl-4-(5-(2,6-dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazole-3-carboxamido)cyclohexane-1-carboxylate.

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3758 - 3770

51
[ 1092397-37-9 ]
[ 61367-07-5 ]
C₆₁H₅₇N₁₃O₁₁S₆ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 6920 - 6928

52
[ 61367-07-5 ]
trans-4-(4-methoxycarbonylbutylamino)cyclohexane-1-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 6920 - 6928

53
[ 61367-07-5 ]
[ 100-52-7 ]
trans-4-(benzylamino)cyclohexane-1-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 6920 - 6928

54
[ 61367-07-5 ]
[ 100-52-7 ]
trans-4-[benzyl(4-methoxycarbonylbutyl)amino]cyclohexane-1-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 6920 - 6928

55
[ 61367-07-5 ]
[ 90349-23-8 ]
methyl trans-4-[(5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)carbonyl]amino}cyclohexanecarboxylate [ No CAS ]