[ CAS No. 149423-70-1 ] {[proInfo.proName]}

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Quality Control of [ 149423-70-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 149423-70-1 ]

SDS Specification

Alternatived Products of [ 149423-70-1 ]

Product Details of [ 149423-70-1 ]

CAS No. :	149423-70-1	MDL No. :	MFCD06657668
Formula :	C₁₄H₂₀N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JQVBZZUMWRXDSQ-UHFFFAOYSA-N
M.W :	248.32	Pubchem ID :	18650082
Synonyms :

Calculated chemistry of [ 149423-70-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	70.13
TPSA :	64.35 ?2

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) :	-6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.54
Log Po/w (XLOGP3) :	1.83
Log Po/w (WLOGP) :	2.03
Log Po/w (MLOGP) :	1.68
Log Po/w (SILICOS-IT) :	1.45
Consensus Log Po/w :	1.9

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.45
Solubility :	0.883 mg/ml ; 0.00356 mol/l
Class :	Soluble
Log S (Ali) :	-2.8
Solubility :	0.392 mg/ml ; 0.00158 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.4
Solubility :	0.1 mg/ml ; 0.000403 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.01

Safety of [ 149423-70-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 149423-70-1 ]

* 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.

Downstream synthetic route of [ 149423-70-1 ]

[ 149423-70-1 ] Synthesis Path-Downstream 1~12

1
[ 634-47-9 ]
[ 149423-70-1 ]
cis-[4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-carbamic acid benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With IEA; In isopropyl alcohol; at 170.0℃; for 5.0h;	To a solution of <strong>[149423-70-1]cis-(4-amino-cyclohexyl)-carbamic acid benzyl ester</strong> (0.5 g, 0.0020 mol) in 1 ml_ 2-propanol was added 2-chloro-4-methyl-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 / CH2Cl2) to yield cis-[4-(4-methyl-quinolin-2-ylamino)-cyclohexyl]-carbamic acid benzyl ester (3.3 g, 53%) as a colorless oil. ESI MS m/e 390.2 M + H+; 1H NMR (400 MHz, DMSO-d6) delta 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, 2 H), 1.70-1.59 (m, 6 H).

Reference： [1]Patent: EP1464335,2004,A2 .Location in patent: Page/Page column 293

2
[ 509143-03-7 ]
[ 149423-70-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With trifluoroacetic acid; In dichloromethane; at 20.0℃; for 4.0h;	Step B: Synthesis of cis-(4-amino-cyclohexyl)-carbamic acid benzyl ester. To a solution of cis-(4-tert-butoxycarbonylamino-cyclohexyl)-carbamic acid benzyl ester (6.2 g, 0.018 mol) in 40 mL CH2Cl2 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 CH2Cl2. The organic layer was extracted with 30 mL of a dilute NaOH (aq) / NaHCO3 (aq) solution. The aqueous layer was back extracted twice with CH2Cl2 and the organic layers combined, dried over MgSO4, and concentrated to yield cis-(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+.

Reference： [1]Patent: EP1464335,2004,A2 .Location in patent: Page/Page column 293

3
[ 149423-70-1 ]
[ 2927-71-1 ]
[ 1192712-34-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20.0℃; for 20.0h;	To a mixture of 2,4-dichloro-5-fluoropyrimidine (226 mg, 1.35 mmol) and benzyl (ls,4s)-4-aminocyclohexylcarbamate (335 mg, 1.35 mmol) in CH3CN (6 mL), DIEA (0.600 mL, 3.45 mmol) was added. The mixture was stirred at room temperature for 20 h. Water and EtOAc were added. The organic phase was separated, washed with IN HCl, dried over Na2SO4, concentrated in vacuo to give benzyl (ls,4s)-4-(2-chloro-5-fluoropyrimidin-4- ylamino)cyclohexylcarbamate (511 mg).

Reference： [1]Patent: WO2009/131687,2009,A2 .Location in patent: Page/Page column 189

4
[ 36082-50-5 ]
[ 149423-70-1 ]
[ 1192712-36-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20.0℃; for 20.0h;	To a mixture of 2,4-dichloro-5-bromopyrimidine (244 mg, 1.07 mmol) and benzyl (ls,4s)-4-aminocyclohexylcarbamate (266 mg, 1.07 mmol) in CH3CN (5 mL), DIEA (0.373 <n="192"/>mL, 2.14 mmol) was added. The mixture was stirred at room temperature for 20 h. Water and EtOAc were added. The organic phase was separated, washed with IN HCl, then with 5% NaHCCbeta, dried over Na2SO4, concentrated in vacuo to give benzyl (ls,4s)-4-(5-bromo-2- chloropyrimidin-4-ylamino)cyclohexylcarbamate

Reference： [1]Patent: WO2009/131687,2009,A2 .Location in patent: Page/Page column 190-191

5
[ 149423-69-8 ]
[ 149423-70-1 ]

Yield	Reaction Conditions	Operation in experiment
	With water; triphenylphosphine; In tetrahydrofuran; at 70.0℃; for 20.0h;	To a solution of benzyl (ls,4s)-4-azidocyclohexylcarbamate (0.410 g, 1.50 mmol) in THF (8 mL) and H2O (0.100 mL, 5.56 mmol) at room temperature, Ph3P (0.590 g, 2.25 mmol) was added. The solution was stirred at 7O0C for 20 h. EtOAc and IN HCl were added. The aqueous phase was separated, washed with EtOAc. It was then basified with 5N NaOH to pH 12. The free amine product was extracted with EtOAc. The EtOAc solution was dried over Na2SO4, and concentrated in vacuo to give benzyl (ls,4s)-4-aminocyclohexylcarbamate (0.270 g).

Reference： [1]Patent: WO2009/131687,2009,A2 .Location in patent: Page/Page column 189

6
[ 149423-70-1 ]
[ 247570-24-7 ]