56239-26-0|cis-4-Aminocyclohexanol hydrochloride| Ambeed

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Quality Control of [ 56239-26-0 ] Purity: 97% SDS Specification

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Product Details of [ 56239-26-0 ]

CAS No. :	56239-26-0
Formula :	C₆H₁₄ClNO
M.W :	151.63
SMILES Code :	O[C@H]1CC[C@@H](N)CC1.[H]Cl
MDL No. :	MFCD07366531
InChI Key :	RKTQEVMZBCBOSB-UHFFFAOYSA-N
Pubchem ID :	522619

Safety of [ 56239-26-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 56239-26-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	0
Fraction Csp3	1.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	39.68
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.25 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.74
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.05
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.57
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.39
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.55

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.25
Solubility	8.6 mg/ml ; 0.0567 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.29
Solubility	7.77 mg/ml ; 0.0512 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.1
Solubility	122.0 mg/ml ; 0.802 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.7 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.03

Application In Synthesis of [ 56239-26-0 ]

* 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 [ 56239-26-0 ]

[ 56239-26-0 ] Synthesis Path-Downstream 1~28

1
[ 916225-31-5 ]
[ 56239-26-0 ]
N-{5-[2-bromo-5-(4-hydroxy-cyclohexylsulfamoyl)-thiophen-3-yl]-4-methyl-thiazol-2-yl}acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 20℃;	4-[2-(acetylamino)^-methyl-l,3-thiazol-5-yl]-5-bromothiophene-2-sulfonyl chloride, prepared as in Step III of Example 23 (300 mg; 0.72 mmol; 1 eq), is dissolved in anhydrous DCM (20 ml). The reaction is put under nitrogen. Triethylamine (0.7 ml; 5.05 mmol; 7 eq) and <strong>[56239-26-0]trans-4-aminocyclohexanol hydrochloride</strong> (547.1 mg; 3.61 mmol; 5 eq) are added successively. DMF (0.2 ml) is added to dissolve the amine and the reaction mixture is stirred overnight at room temperature. The reaction mixture is then washed with water, NH4Cl sat., brine and dried over MgSO4, affording the title compound (120 mg; 21percent).M (ESI): 493.04; M+(ESI):495.03. HPLC (method A), Rt: 2.98 min (purity: 62.8percent).

References: [1]Patent: WO2006/125803,2006,A1 .Location in patent: Page/Page column 62.

2
[ 923022-57-5 ]
[ 56239-26-0 ]
6-cis-(4-amino-cyclohexyloxy)-2-(4-methoxy-benzyl)-7-propyl-2H-isoquinolin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		58 mg (0.38 mmol) of cis 4-aminocyclohexanol hydrochloride were dissolved in 10 ml of dimethyl acetamide. Under argon, 38 mg (0.96 mmol) of sodium hydride (60percent) were added and the reaction was stirred for 30 minutes at room temperature. After addition of a solution of 100 mg (0.31 mmol) of 6-fluoro-2-(4-methoxy-benzyl)-7-propyl-2H- isoquinolin-1-one (105) the solution was stirred at 80 0C. To obtain complete conversion, the same amounts of the 4-aminocyclhexanol hydrochloride and sodium hydride were added twice and the temperature was increased to 110 0C. After complete conversion, the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried with magnesium sulfate and evaporated. After purification by preparative HPLC the desired product was isolated as trifluoroacetate. Rt = 1.14 min (Method C). Detected mass: 421.6 (M+H+).

References: [1]Patent: WO2007/12422,2007,A1 .Location in patent: Page/Page column 68.

3
[ 923022-82-6 ]
[ 56239-26-0 ]
[ 923022-83-7 ]

Yield	Reaction Conditions	Operation in experiment
		90 mg (0.59 mmol) of <strong>[56239-26-0]cis 4-amino-cyclohexanol hydrochloride</strong> were dissolved in 10 ml dimethyl acetamide and 59.3 mg (1.48 mmol) of sodium hydride (60percent) were added. After stirring 30 minutes at room temperature, a solution of 200 mg (0.49 mmol) of 7- benzylsulfanyl-6-fluoro-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one (126) in 20 ml of dimethyl acetamide was added and the mixture was stirred at 80 0C for 1 h, then at 130 0C for 3 h. Another 1.2 equivalents of <strong>[56239-26-0]cis 4-amino-cyclohexanol hydrochloride</strong> and 2.5 equivalents of sodium hydride were added and the temperature was increased to 160 0C. After 8h the solution is cooled down to room temperature and the solvent is removed under reduced pressure. The residue is dissolved in dichloromethane, washed with water and dried with magnesium sulfate. After evaporation of the solvent and purification by preparative HPLC, the title compound was isolated as trifluoroacetate. R1 = 1.18 min (Method C). Detected mass: 501.6 (M+H+).

References: [1]Patent: WO2007/12422,2007,A1 .Location in patent: Page/Page column 76.

4
[ 56239-25-9 ]
[ 56239-26-0 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 30.0 g (0.265 mol) of cyclohexanone oxime in 300 ml of methylene chloride and 38 ml of ethanol was slowly added at 0 0C 34.5 g (0.318 mol) of tert- butyl-hypochlorite. The resulting dark blue solution was cooled to -2O0C and then 31.9 g (0.398 mol) of 1 ,3-cyclohexadiene were added and the mixture was stored in a freezer at 5°C for 2 days until the blue color had disappeared. The reaction mixture was concentrated to 50percent of its volume and then 600 ml of diethyl ether were slowly added. After stirring overnight the resulting precipitate was isolated by suction to yield 29,0 g of 2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene hydrochloride. 5.0 g (0.045 mol) of this material were hydrogenated with 3.0 g (0.013 mol) platinum oxide at 2 bar hydrogen pressure. After 7 h the catalyst was filtered off and a solution of 20 ml 4 M hydrochloric acid in dioxane was added. After evaporation the residue was recrystallized from 30 ml isopropanol giving 3.1 g of cis-4-aminocyclohexanol hydrochloride.

References: [1]Patent: WO2007/12422,2007,A1 .Location in patent: Page/Page column 82-83.

5
[ 1214901-12-8 ]
[ 56239-26-0 ]
[ 1214893-44-3 ]

Yield	Reaction Conditions	Operation in experiment
24%	With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; at 20 - 100℃;Inert atmosphere;	B. cis-4-(2-(4-(Trifluoromethyl)phenylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-ylamino)cyclohexanol. To an orange solution of 5-bromo-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-c]pyridin-2-amine (0.300 g, 0.840 mmol) in dioxane (15 mL) was added <strong>[56239-26-0]cis-4-aminocyclohexanol hydrochloride</strong> (0.255 g, 1.680 mmol), sodium tert-butoxide (0.242 g, 2.52 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.097 g, 0.168 mmol) and tris(dibezylideneacetone)dipalladium (0) (0.081 g, 0.088 mmol) at room temperature under nitrogen. The reaction mixture was heated at 100° C. for 1 h under nitrogen. Upon completion of reaction as indicated by LCMS the reaction mixture was poured into water/brine, and extracted with ethyl acetate several times. The combined organic layer was dried over anhydrous magnesium sulfate and concentrated. The crude mixture was purified by silica gel column chromatography (eluding with 0-100percent ethyl acetate in hexanes) to give the title compound as a brownish yellow solid (100percent pure, 0.078 g, 24percent yield). 1H-NMR (400 MHz, DMSO-d6) delta (ppm) 10.03 (s, 1H), 7.90-7.98 (m, 2H), 7.58-7.66 (m, 2H), 7.44 (t, J=8.27 Hz, 1H), 6.77 (dd, J=1.00, 8.57 Hz, 1H), 6.19-6.26 (m, 2H), 4.51 (d, J=3.17 Hz, 1H), 3.80 (d, J=2.54 Hz, 1H), 3.55-3.66 (m, 1H), 1.83-1.96 (m, 2H), 1.56-1.78 (m, 6H); MS (ESI) m/z 392.39 [M+1]+

References: [1]Patent: US2010/93698,2010,A1 .Location in patent: Page/Page column 98-99.

6
[ 22509-74-6 ]
[ 56239-26-0 ]
[ 478832-25-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate; In water; at 20℃;	EXAMPLE 86[0124] Preparation of 4-((R)-Tetrahydrofuran-3-yloxy)-5-(2,3- dihydrobenzo[b][l,4]dioxin-6-yl)-N-((ls,4S)-4-methoxycyclohexyl)pyrimidin-2-amineJ.: Preparation of Starting Material 4-Methoxycyclohexanamine HydrochlorideReagents and Conditions: a) K2CO3 H2; b) KHMDS, MeI, and THF; c) NH2NH2, EtOH, then 4M HCI H2N HCIStep 1-1: Preparation of 2-((ls,4s)-4-Hydroxycyclohexyl)isoindoline-l,3-dione (2) [0125] To a stirred solution of cis-4-aminocyclohexanol HCl (107 mg, 0.71 mmol) in H2O(1.7 mL) at room temperature was added K2CO3 (174 mg, 1.25 mmol), followed by N- carboethoxyphthalimide (174 mg, 0.79 mmol). After stirring at room temperature for 30 min, the solid was filtered, washed with H2O, and dried in vacuo to provide the title compound (140 mg, 81percent) as a white solid. 1H NMR (300 MHz, CDCl3) delta 7.82 (m, IH), 7.79 (m, IH), 4.10 (m, IH), 2.64 (m, IH), 1.5-2.0 (set of m, 4H). MS (ESI) m/z: Found: 491 (2M+ + 1), CaIc. 245(M+).

References: [1]Patent: WO2010/68863,2010,A2 .Location in patent: Page/Page column 75-76.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 10003 - 10015.

7
[ 1207541-14-7 ]
[ 56239-26-0 ]
[ 1207540-16-6 ]

Yield	Reaction Conditions	Operation in experiment
59%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 80℃; for 6h;	EXAMPLE 624-[7-(4-morpholin-4-yl-phenyl)-[1,6]naphthyridin-5-ylamino]-cyclohexanol50 mg (0.11 mmol) 6.6, 38 mg (0.25 mmol) <strong>[56239-26-0]cis-4-aminocyclohexanol hydrochloride</strong> and 50 mul (0.29 mmol) diisopropylethylamine were stirred into 0.5 ml N-methylpyrrolidone for 6 h at 80° C.The mixture was purified by chromatography (RP-HPLC-MS). The corresponding fractions were freeze-dried.Yield: 35 mg (0.07 mmol=59percent of theory)Analysis: HPLC-MS (method D): Rt: 1.24 min, (M+H)+: 405

References: [1]Patent: US2011/201608,2011,A1 .Location in patent: Page/Page column 23-24.

8
[ 56239-26-0 ]
[ 1374215-14-1 ]

References: [1]Patent: US2012/108566,2012,A1 .

9
[ 56239-26-0 ]
[ 1374211-56-9 ]

References: [1]Patent: US2012/108566,2012,A1 .

10
[ 40296-46-6 ]
[ 56239-26-0 ]
[ 1374215-13-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 110℃; for 6h;	A mixture of ethyl 4,6-dichloronicotinate (160 mg, 0.727 mmol), <strong>[56239-26-0](1s,4s)-4-aminocyclohexanol hydrochloride</strong> (110 mg, 0.726 mmol) and DIPEA (0.330 mL, 1.89 mmol) in NMP (5 mL) was stirred at 110 C for 6 h. Water and EtOAc were added. The organic phase was separated, washed with 5percent NaHCO3, dried over Na2SO4, concentrated in vacuo to give ethyl 6-chloro-4-((1s,4s)-4-hydroxycyclohexylamino)nicotinate as a solid (200 mg).

References: [1]Patent: US2012/108566,2012,A1 .Location in patent: Page/Page column 79.

11
[ 1269815-50-0 ]
[ 56239-26-0 ]
[ 1377698-66-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dimethyl sulfoxide; at 95 - 100℃; for 40h;	To tert-butyl 3-(5-chloro-2-fluoropyridin-4-yl)phenyl((tetrahydro-2H-pyran-4- yl)methyl)carbamate (440 mg, 1.045 mmol) was added DMSO (4 ml), TEA (0.729 ml, 5.23 mmol), and (ls,4s)-4-aminocyclohexanol hydrochloride (476 mg, 3.14 mmol) . The reaction was stirred at 95-100 °C for 40 hr. The reaction was followed by LCMS. The reaction was let cool, added 250 ml of ethyl acetate, washed with saturated sodium bicarbonate, water (2x), filtered and concentrated to constant mass. The crude was purified by silica gel chromatography using 12g column eluting with 30-85percent ethyl acetate with heptane. The desired fractions were concentrated to constant mass, giving 363 mg of the titled compound as free base used without further purification. LCMS (m/z): 516.2 (MH+), rt = 0.80 min.

References: [1]Patent: WO2012/66065,2012,A1 .Location in patent: Page/Page column 124.

12
[ 5414-19-7 ]
[ 56239-26-0 ]
[ 1228947-14-5 ]