[ CAS No. 317595-54-3 ] {[proInfo.proName]}

Name: 317595-54-3|tert-Butyl (2-aminocyclohexyl)carbamate|98%
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Quality Control of [ 317595-54-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 317595-54-3 ]

Product Details of [ 317595-54-3 ]

CAS No. :	317595-54-3	MDL No. :	MFCD04038473
Formula :	C₁₁H₂₂N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AKVIZYGPJIWKOS-UHFFFAOYSA-N
M.W :	214.30	Pubchem ID :	3268011
Synonyms :

Calculated chemistry of [ 317595-54-3 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.91
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	60.1
TPSA :	64.35 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) :	-6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.51
Log Po/w (XLOGP3) :	1.32
Log Po/w (WLOGP) :	1.78
Log Po/w (MLOGP) :	1.15
Log Po/w (SILICOS-IT) :	0.64
Consensus Log Po/w :	1.48

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.74
Solubility :	3.93 mg/ml ; 0.0184 mol/l
Class :	Very soluble
Log S (Ali) :	-2.27
Solubility :	1.14 mg/ml ; 0.00534 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.69
Solubility :	4.42 mg/ml ; 0.0206 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.02

Safety of [ 317595-54-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 317595-54-3 ]

* 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 [ 317595-54-3 ]
Downstream synthetic route of [ 317595-54-3 ]

[ 317595-54-3 ] Synthesis Path-Upstream 1~3

1
[ 24424-99-5 ]
[ 694-83-7 ]
[ 317595-54-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: With hydrogenchloride In methanol for 2 h; Stage #2: for 3 h;	General procedure: The 800 mL of methanol containing 16.53 g (0.453 mol) ofdry HCl was added dropwise to the solution of 51.78 g (0.453mol) of trans-(1R,2R)-()-1,2-diaminocyclohexane in 80 mLof methanol for 2 h. After adding 50 mL of water, 98.97 g(0.453 mol) of di-t-butyl dicarbonate was added by portions for1 h. The mixture was stirred for 2 h, and then methanol wasremoved. The residue was rinsed with 900 mL of ether and theinsoluble matter was filtered off and dried. The crude productwas dissolved in 800 mL of water and then extracted with amixture of 500 mL of CH2Cl2 and 340 mL of 2 M NaOH. Theorganic layer was retained and treated with MgSO4 and the solvent evaporated. Recrystallization from 900 mL of ligroingave 67.87 g (70percent) of trans-(1R,2R)-1-Boc-amino-2-aminocyclohexane.
64%	at 20℃; Cooling with ice	A solution of Boc₂O (3.03 g, 13.9 mmol) in dichloromethane (25 mL) was added dropwise with stirring to a solution of 1,2-diaminocyclohexane (5 mL, 21.6 mmol) in CH₂Cl₂ (25 mL) under ice bath within 30 minutes. The solution was stirred at room temperature overnight and then concentrated. 25 mL water was added. The solution was adjusted to pH 5 with 1M HCl and extracted with ether (25 mL × 3). The water phase was collected and adjusted to pH 10 with 1 M NaOH aq then extracted with EA (25 mL × 3) to collect the organic phase. The organic phase was dried with anhydrous Na₂SO₄ and concentrated under reduced pressure to give white solid compound 5 with the 64percent yield. ¹H NMR (400 MHz, CDCl₃) δ 4.40 (s, 1H), 3.08 (s, 1H), 2.81 (s, 1H), 2.26 (d, J = 10.1 Hz, 1H), 1.91 (s, 2H), 1.64 (d, J = 10.8 Hz, 2H), 1.38 (s, 9H), 1.19 - 1.01 (m, 4H).

Reference： [1] Archiv der Pharmazie, 2012, vol. 345, # 11, p. 896 - 901
[2] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 3, p. 312 - 321
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3793 - 3797
[4] Patent: US5021571, 1991, A,
[5] Patent: US5089663, 1992, A,

2
[ 1436-59-5 ]
[ 317595-54-3 ]

Reference： [1] Patent: US2005/20645, 2005, A1,

3
[ 21436-03-3 ]
[ 317595-54-3 ]

Reference： [1] Patent: US2005/20645, 2005, A1,

[ 317595-54-3 ] Synthesis Path-Downstream 1~80

1
4-(N-chloroacetyl-N-methylamino)benzoic acid [ No CAS ]
[ 317595-54-3 ]
(2-{4-[(2-chloroacetyl)methylamino]benzoylamino}cyclohexyl)carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-ethyl-N,N-diisopropylamine; HATU; In DMF (N,N-dimethyl-formamide); at 20℃; for 0.5h;	Part A. 4-[(2-Chloro-acetyl)-methyl-amino]-benzoic acid (0.23 g, 1.0 mmol.) was stirred in DMF (2 mL) at RT under N2-(2-Amino-cyclohexyl)-carbamic acid tert-butyl ester (0.21 g, 1.0 mmol), HATU (0.57 g, 1.5 eq) and DIEA (0.5 mL, 2.9 eq) were added. The mixture was stirred at RT for 30 min. It was partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated to dryness to give (2-{4-[(2-chloro-acetyl)-methyl-amino]-benzoylamino}-cyclohexyl)-carbamic acid tert-butyl ester (0.40 g, yield: 95%).

Reference： [1]Patent: US2003/232804,2003,A1 .Location in patent: Page 103

2
[ 4857-06-1 ]
[ 317595-54-3 ]
C₁₈H₂₆N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	at 140℃; for 3h;	A mixture of 2-chloro-1H-benzimidazole (0.0189 mol) and 1,1-dimethylethyl 2-aminocyclohexanecarbamoate (0.04725 mol) (prepared according to A1a))was stirred at 140C for 3 hours, then brought to room temperature and taken up in CH2Cl2/CH3OH. The same procedure was repeated 3 times on the same quantities of 2-chloro-1H-benzimidazole and 1,1-dimethylethyl 2-aminocyclohexanecarbamoate. The mother layers were brought together, dried (MgSO4), filtered and the solvent was evaporated. The residue (28g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/ NH4OH 96/4/0.1; 15-35mum). Two fractions were collected and the solvent was evaporated, yielding 4.5g of intermediate (84) (24%).

Reference： [1]Patent: EP1196410,2004,B1 .Location in patent: Page 40

3
[ 317595-54-3 ]
[ 439151-23-2 ]
[ 7087-68-5 ]
cis-{2-[2-(2-isopropylamino-5-trifluoromethylbenzoylamino)acetylamino]cyclohexyl}carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide;	(144a) <strong>[317595-54-3]N-tert-Butyloxycarbonylcyclohexane-(cis)-1,2-diamine</strong> (518 mg) was dissolved in CH2Cl2 (45 mL) and DMF (15 mL) prior to the addition of Hunig's base (1.7 mL) and ([2-(isopropylamino)-5-(trifluoromethyl)benzoylamino]acetic acid (incorporated Example 143 into Example 122) (400 mg) and HATU (1.84 g) at rt. The reaction was stirred for 8 h and quenched with water. The organic layer was washed with 1 N HCl, aqueous NaHCO3, 5% aqueous LiCl, and brine. The organic layer was dried, filtered, and concentrated. Flash chromatography of the residue provided cis-{2-[2-(2-isopropylamino-5-trifluoromethylbenzoylamino)acetylamino]cyclohexyl}carbamic acid tert-butyl ester (534 mg). MS found: (M-Boc+H)+=401.1.

Reference： [1]Patent: US2003/4151,2003,A1

4
[ 317595-54-3 ]
[ 364385-74-0 ]
cis-N-tert-butoxycarbonyl-2-(2-ethoxycarbonyl-6-methoxyquinazolin-4-yl)aminocyclohexylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In water; toluene;	Step 1 cis-N-tert-Butoxycarbonyl-2-(2-ethoxycarbonyl-6-methoxyquinazolin-4-yl)aminocyclohexylamine A solution of 1.96 g of 4-chloro-2-ethoxycarbonyl-6-methoxyquinazoline in 70 mL of toluene was combined with 1.58 g of cis-2-tert-butoxycarbonylaminocyclohexylamine and 0.74 g of triethylamine, and heated under reflux for 15 hours. After concentrating, the mixture was combined with water, extracted with chloroform, and dried. After the solvent was distilled off, the residue was purified by column chromatography on silica gel (chloroform) to obtain 2.70 g of the desirable compound.

Reference： [1]Patent: US2003/119855,2003,A1

5
[ 317595-54-3 ]
[ 554-68-7 ]

Yield	Reaction Conditions	Operation in experiment
		The resulting triethylammonium chloride was removed by filtration and to the filtrate was added N-(t-butoxycarbonyl)-trans 1,2-diaminocyclohexane.
		The resulting triethylammonium chloride was removed by filtration and to the filtrate was added N-(t-butoxycarbonyl)-trans 1,2-diaminocyclohexane.

Reference： [1]Patent: US5021571,1991,A
[2]Patent: US5089663,1992,A

6
[ 24424-99-5 ]
[ 694-83-7 ]
[ 317595-54-3 ]

Yield	Reaction Conditions	Operation in experiment
77%		General procedure: The 800 mL of methanol containing 16.53 g (0.453 mol) ofdry HCl was added dropwise to the solution of 51.78 g (0.453mol) of trans-(1R,2R)-()-1,2-diaminocyclohexane in 80 mLof methanol for 2 h. After adding 50 mL of water, 98.97 g(0.453 mol) of di-t-butyl dicarbonate was added by portions for1 h. The mixture was stirred for 2 h, and then methanol wasremoved. The residue was rinsed with 900 mL of ether and theinsoluble matter was filtered off and dried. The crude productwas dissolved in 800 mL of water and then extracted with amixture of 500 mL of CH2Cl2 and 340 mL of 2 M NaOH. Theorganic layer was retained and treated with MgSO4 and the solvent evaporated. Recrystallization from 900 mL of ligroingave 67.87 g (70%) of trans-(1R,2R)-1-Boc-amino-2-aminocyclohexane.
64%	In dichloromethane; at 20℃;Cooling with ice;	A solution of Boc2O (3.03 g, 13.9 mmol) in dichloromethane (25 mL) was added dropwise with stirring to a solution of 1,2-diaminocyclohexane (5 mL, 21.6 mmol) in CH2Cl2 (25 mL) under ice bath within 30 minutes. The solution was stirred at room temperature overnight and then concentrated. 25 mL water was added. The solution was adjusted to pH 5 with 1M HCl and extracted with ether (25 mL × 3). The water phase was collected and adjusted to pH 10 with 1 M NaOH aq then extracted with EA (25 mL × 3) to collect the organic phase. The organic phase was dried with anhydrous Na2SO4 and concentrated under reduced pressure to give white solid compound 5 with the 64% yield. 1H NMR (400 MHz, CDCl3) delta 4.40 (s, 1H), 3.08 (s, 1H), 2.81 (s, 1H), 2.26 (d, J = 10.1 Hz, 1H), 1.91 (s, 2H), 1.64 (d, J = 10.8 Hz, 2H), 1.38 (s, 9H), 1.19 - 1.01 (m, 4H).
12.0 g (58%)	In tetrahydrofuran; ethyl acetate;	In the first step, to a solution consisting of 125 ml (1 mole) trans 1,2-diaminocyclohexane and 400 ml dry THF was added 22 ml (96 mmol) di-tertbutyldicarbonate. The reaction was gently refluxed for 3 hr, cooled to room temperature and allowed to stand overnight. The reaction mixture was then filtered and concentrated under reduced pressure. The excess trans 1,2-diaminocyclohexane was recovered by vacuum distillation. The slurry remaining in the distillation flask was dissolved in ethyl acetate and purified by flash chromatography (silica gel, ethyl acetate as eluant), followed by recrystallization from ethyl ether to give 12.0 g (58%) of N-(t-butoxycarbonyl)-trans-1,2-diaminocyclohexane as a white solid mp 88-91 C.

12.0 g (58%)

In tetrahydrofuran; ethyl acetate;

In the first step, to a solution consisting of 125 ml (1 mole) trans 1,2-diaminocyclohexane and 400 ml dry THF was added 22 ml (96 mmol) di-tertbutyldicarbonate. The reaction was gently refluxed for 3 hr, cooled to room temperature and allowed to stand overnight. The reaction mixture was then filtered and concentrated under reduced pressure. The excess trans 1,2-diaminocyclohexane was recovered by vacuum distillation. The slurry remaining in the distillation flask was dissolved in ethyl acetate and purified by flash chromatography (silica gel, ethyl acetate as eluant), followed by recrystallization from ethyl ether to give 12.0 g (58%) of N-(t-butoxycarbonyl)-trans-1,2-diaminocyclohexane as a white solid mp 88-91 C.

Reference： [1]Archiv der Pharmazie,2012,vol. 345,p. 896 - 901
[2]Bulletin of the Chemical Society of Japan,2017,vol. 90,p. 312 - 321
[3]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3793 - 3797
[4]Patent: US5021571,1991,A
[5]Patent: US5089663,1992,A

7
[ 1436-59-5 ]
[ 317595-54-3 ]

Yield	Reaction Conditions	Operation in experiment
		REFERENTIAL EXAMPLE 66 tert-Butyl (1R,2S)-2-aminocyclohexylcarbamate: The title compound was obtained from cis-1,2-cyclohexanediamine in a similar manner to Referential Example 61. 1H-NMR (CDCl3) delta: 1.30-1.70(17H,m), 2.98-3.05(1H,m), 3.60(1H,br.s), 4.98(1H,br.s). MS (FAB) m/z: 215(M+H)+.

Reference： [1]Patent: US2005/20645,2005,A1

8
[ 21436-03-3 ]
[ 317595-54-3 ]

Yield	Reaction Conditions	Operation in experiment
		REFERENTIAL EXAMPLE 64 tert-Butyl (1R,2R)-2-aminocyclohexylcarbamate: The title compound was obtained from (+-)-trans-1,2-cyclohexanediamine in a similar manner to Referential Example 61. m.p.79-81. 1H-NMR (CDCl3) delta: 1.05-1.34(4H,m), 1.45(9H,s), 1.68-1.75(2H,m), 1.92-2.02(2H,m), 2.32(1H,dt,J=10.3, 3.9 Hz), 3.08-3.20(1H,m), 4.50(1H,br.s). MS (FAB) m/z: 215(M+H)+.

Reference： [1]Patent: US2005/20645,2005,A1

9
[ 317595-54-3 ]
[ 32315-10-9 ]
[ 50712-59-9 ]
[ 1300730-77-1 ]

Yield	Reaction Conditions	Operation in experiment
58%		Example 53 Ethyl 2-(4-(3-(2-(tert-butoxycarbonylamino)cyclohexyl)ureido)-2- chlorophenyl)acetate; [0383] To a solution of ethyl 2-(4-amino-2-chlorophenyl)acetate (178 mg, 0.833 mmol) in dry dichloromethane (5 mL), was added triethylamine (2.32 mL, 16.66 mmol) followed by triphosgene (247 mg, 0.833 mmol). solution in dichloromethane (1 mL). The reaction mixture was stirred at room temperature for 1 h. To this mixture was then added tert-butyl 2- aminocyclohexylcarbamate (357 mg, 1.67 mmol) in dichloromethane (1 mL). The reaction mixture was stirred at room temperature for 4 h and concentrated. The residue was dissolved in ethyl acetate and washed with water (2 x 20 mL), brine (10 mL), dried and concentrated. The crude product was purified by flash column chromatography to afford the desired product as a mixture of cis and trans diastereomers (220 mg, 0.485 mmol, 58%). NMR : 1.23-1.28 (m, 6H), 1.38 (s, 9H), 1.70-1.73 (m, 2H), 2.01 -2.08 (m, 2H), 3.29-3.32 (m, 1H), 3.53-3.58 (m, 1 H), 3.68 (s, 2H), 4.1 1-4.19 (m, 2H), 5.01 (d, 1H, J = 8.8 Hz), 5.57 (d, 1H, J = 8 Hz), 7.13 (d, 1H, J= 8.4 Hz), 7.20 (d, 1H, J= 6.8 Hz), 7.41 (s, 1H), 7.46 (s, 1H).

Reference： [1]Patent: WO2011/56652,2011,A1 .Location in patent: Page/Page column 133

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[ 317595-54-3 ]
[ 122-03-2 ]
[ 1416225-79-0 ]