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[ CAS No. 224309-64-2 ] {[proInfo.proName]}

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Chemical Structure| 224309-64-2
Chemical Structure| 224309-64-2
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Product Details of [ 224309-64-2 ]

CAS No. :224309-64-2 MDL No. :MFCD06658349
Formula : C11H21NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :DQARDWKWPIRJEH-UHFFFAOYSA-N
M.W : 215.29 Pubchem ID :1514287
Synonyms :

Calculated chemistry of [ 224309-64-2 ]

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 : 58.55
TPSA : 58.56 Ų

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) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.47
Log Po/w (XLOGP3) : 1.58
Log Po/w (WLOGP) : 1.81
Log Po/w (MLOGP) : 1.15
Log Po/w (SILICOS-IT) : 0.88
Consensus Log Po/w : 1.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.91
Solubility : 2.67 mg/ml ; 0.0124 mol/l
Class : Very soluble
Log S (Ali) : -2.42
Solubility : 0.818 mg/ml ; 0.0038 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.47
Solubility : 7.29 mg/ml ; 0.0339 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.96

Safety of [ 224309-64-2 ]

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 [ 224309-64-2 ]

* 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 [ 224309-64-2 ]
  • Downstream synthetic route of [ 224309-64-2 ]

[ 224309-64-2 ] Synthesis Path-Upstream   1~22

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Reference: [1] Patent: WO2007/130898, 2007, A1, . Location in patent: Page/Page column 44
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Reference: [1] Chemical Science, 2016, vol. 7, # 8, p. 5371 - 5383
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YieldReaction ConditionsOperation in experiment
87%
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -60℃; for 1.25 h;
Stage #2: With triethylamine In dichloromethane at -60 - 20℃;
A methylene chloride solution (6 ml) of dimethyl sulfoxide (2.0 ml, 28.2 mmol) was added dropwise to a methylene chloride solution (30 ml) of oxalyl chloride (1.7 ml, 19.5 mmol) at -60°C over a period of 10 minutes and stirred at -60°C for another 10 minutes. Then, a methylene chloride solution (140 ml) of tert-butyl 4-hydroxycyclohexylcarbamate (2.56 g, 11.9 mmol) was added dropwise thereto over a period of 35 minutes, and the resulting mixture was stirred at -60°C for 40 minutes. After triethylamine (8.4 ml, 60.3 mmol) was added thereto at -60°C, the resulting mixture was warmed up to room temperature spontaneously. Water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous ammonium chloride solution and a saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate) to obtain tert-butyl 4-oxocyclohexylcarbamate (2.23 g, 87percent).1H-NMR (DMSO-d6): 1.06-1.20 (4H, m), 1.35 (9H, s), 1.69-1.76 (4H, m), 3.12-3.31 (2H, m), 4.48 (1H, s), 6.64 (1H, d, J=7.5Hz).
85.7% With pyridinium chlorochromate In chloroform at 0 - 20℃; for 3 h; Step-2,
Synthesis of tert-butyl (4-oxocyclohexyl)carbamate:
A solution of tert-butyl (4-oxocyclohexyl) carbamate (5g, 0.0232 mol) in chloroform (50ml_) was cooled to 0 °C and pyridiniumchlorochromate (12.49g, 0.058mol) was added portion wise. After addition completed the resulting mixture was allowed to RT and stirred for 3 h. The reaction mixture was diluted with chloroform (100ml_) and washed with brine, water, dried over sodium sulphate and evaporated under vacuum. The residue was purified by column chromatography on silica gel (5percent MeOH-DCM) to afford tert-butyl (4-oxocyclohexyl)carbamate of 4.2g, 85.7percent yield.1HNMR (CDCI3, 300MHz): δ 4.5 (m, 1 H), 3.91 (m, 1 H), 2.4(m, 4H), 2.2 (m, 2H), 1.6 (m, 2H), 1 .45 (m, 9H).
82.1% With Dess-Martin periodane In dichloromethane at 20℃; Cooling with ice Dess-Martin oxidizer (29.0 g, 68.3 mmol) was added dropwise to a solution of N-4-Boc-aminocyclohexanol (9.8 g, 45.52 mmol) in dichloromethane (200 mL) with ice-bath stirring. Warm to room temperature and stir the reaction mixture overnight. The mixture was carefully quenched with a saturated aqueous solution of sodium thiosulfate in an ice bath and extracted three times with dichloromethane. The combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Column chromatography on a silica gel column yielded 4-oxo. Tert-butyl cyclohexylcarbamate (7.96 g, yield 82.1percent).
7 g With Dess-Martin periodane In dichloromethane at 20℃; To a solution of tert- v y\ 4-hydroxy- cyclohexylcarbamate (10.0 g, 46.5 mmol) in DCM (100 mL) was added Dess-Martin periodinane (39.4 g, 92.9 mmol) portionwise. The resulting solution was stirred at r.t. overnight and treated with aq. Na2S203 solution and extracted with DCM (3 x 100 mL). The combined organic layers were washed with water (2 x 100 mL) and brine (100 mL), dried over anhydrous Na2SC>4, and concentrated. The residue was purified by column chromatography on silica gel using petroleum ether / EtOAc (V:V, 10: 1) to afford desired product as a white solid (7.0 g, 70percent crude yield).

Reference: [1] Patent: EP1403255, 2004, A1, . Location in patent: Page 71
[2] Medicinal Chemistry Research, 2013, vol. 22, # 6, p. 2633 - 2644
[3] Patent: WO2015/22664, 2015, A1, . Location in patent: Paragraph 00219;00220
[4] Patent: TW2017/36341, 2017, A, . Location in patent: Paragraph 0489-0491
[5] Patent: WO2005/21515, 2005, A2, . Location in patent: Page/Page column 72-73
[6] Patent: WO2013/107291, 2013, A1, . Location in patent: Page/Page column 64
[7] Patent: WO2013/107405, 2013, A1, . Location in patent: Page/Page column 49
[8] Patent: WO2015/10626, 2015, A1, . Location in patent: Page/Page column 64; 65
[9] Patent: WO2015/10297, 2015, A1, . Location in patent: Page/Page column 64
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Reference: [1] Patent: US2004/19058, 2004, A1,
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  • [ 179321-49-4 ]
Reference: [1] Patent: US2015/87600, 2015, A1, . Location in patent: Page/Page column
[2] Patent: US2013/190249, 2013, A1, . Location in patent: Page/Page column
[3] Patent: US2015/31627, 2015, A1, . Location in patent: Page/Page column
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  • [ 179321-49-4 ]
Reference: [1] Patent: US5574044, 1996, A,
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  • [ 24424-99-5 ]
  • [ 6850-65-3 ]
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YieldReaction ConditionsOperation in experiment
87% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 4 h; Inert atmosphere To a solution of di-tert-butyl dicarbonate (4.087 mL, 21.01 mmol) and diisopropylethylamine (2.87 mL, 17.4 mmol) in THF (60 mL) was added (1R,4R)-4-aminocyclohexanol (2.00 g, 17.4 mmol) and was stirred at rt for 4h. The reaction was concentrated to dryness and the residue was dried under reduced pressure to yield the title Compound as a white solid (3.49 g, 87.0percent yield), which was used without further purification.
79% With triethylamine In tetrahydrofuran at 20℃; To a solution of 4-aminocyclohexanol (23 g, 0.2 mol) and Et3N (60 g, 0.6 mol) in THF (230 mL) was added (Boc)20 (87 g, 0.4 mol). The resulting solution was stirred at r.t. overnight. The solvent was removed under reduced pressure and the residue was extracted with EtOAc (3 x 200 mL). The combined organic layers were washed with water (2 x 200 mL) and brine (200 mL), dried over anhydrous Na2SC>4 and concentrated. The residue was purified by column chromatography on silica gel using DCM/ MeOH (V:V, 20: 1) to afford the desired product as a white solid (34 g, 79percent yield). MS: 216.2 (M+l)+.
Reference: [1] Patent: WO2017/100662, 2017, A1, . Location in patent: Page/Page column 103; 123
[2] Patent: WO2013/107405, 2013, A1, . Location in patent: Page/Page column 48-49
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 2017 - 2021
[4] Patent: US5516806, 1996, A,
[5] Patent: WO2013/107291, 2013, A1, . Location in patent: Page/Page column 63; 64
[6] Patent: WO2015/10626, 2015, A1, . Location in patent: Page/Page column 64; 65
[7] Patent: WO2015/10297, 2015, A1, . Location in patent: Page/Page column 64
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YieldReaction ConditionsOperation in experiment
92% With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; for 3 h; Step-1,
Synthesis of tert-butyl (4-hydroxycyclohexyl)carbamate:
A solution of 4-aminocyclohexanol hydrochloride (20 g, 0.132 mol) in 1 , 4-dioxane (400ml_) and NaHC03(38.9 g, 0.463mol) was added to a solution of water (200ml_). The reaction mixture was cooled to 0 °C and Boc-anhydride was added drop wise. The resulting mixture was allowed to RT and stirred for 3h. The mixture was diluted with ethyl acetate (300ml_) and washed with brine and water, dried over sodium sulphate and evaporated under vacuum to afford Tert-butyl (4- hydroxycyclohexyl) carbamate of 26g, 92percent yield.
Reference: [1] Patent: WO2015/22664, 2015, A1, . Location in patent: Paragraph 00217; 00218
[2] Medicinal Chemistry Research, 2013, vol. 22, # 6, p. 2633 - 2644
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YieldReaction ConditionsOperation in experiment
93% With sodium hydroxide In water; <i>tert</i>-butyl alcohol at 20℃; An aqueous solution (52.5 ml) of sodium hydroxide (2.91 g, 72.8 mmol) was added to a t-butanol suspension (122.5 ml) of trans-4-aminocyclohexanol (8.06 g, 70.0 mmol) at room temperature, followed by adding thereto di-t-butyl dicarbonate (15.9 g, 72.9 mmol), and the resulting mixture was stirred overnight at room temperature. Water was added to the reaction mixture, followed by extraction with n-hexane. The suspended organic layer was filtered and the precipitate was dried to obtain tert-butyl 4-hydroxycyclohexylcarbamate (2.70 g) as a white solid. The aqueous layer was neutralized with 1N-hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate) to obtain tert-butyl 4-hydroxycyclohexylcarbamate (11.3 g) (14.0 g in total, 93percent).1H-NMR (DMSO-d6): 1.06-1.20 (4H, m), 1.35 (9H, s), 1.69-1.76 (4H, m), 3.12-3.31 (2H, m), 4.48 (1H, s), 6.64 (1H, d, J=7.5Hz).
Reference: [1] Patent: EP1403255, 2004, A1, . Location in patent: Page 71
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YieldReaction ConditionsOperation in experiment
79% With triethylamine In tetrahydrofuran Step A:
Tert-butyl 4-hydroxycyclohexylcarbamate
To a solution of 4-aminocyclohexanol (23 g, 0.2 mol) and Et3N (60 g, 0.6 mol) in THF (230 mL) was added (Boc)2O (87 g, 0.4 mol).
The resulting solution was stirred at r.t. overnight.
The solvent was removed under reduced pressure and the residue was extracted with EtOAc (3*200 mL).
The combined organic layers were washed with water (2*200 mL) and brine (200 mL), dried over anhydrous Na2SO4 and concentrated.
The residue was purified by column chromatography on silica gel using DCM/MeOH (V:V, 20:1) to afford the desired product as a white solid (34 g, 79percent yield). MS: 216.2 (M+1)+.
Reference: [1] Patent: US2015/87600, 2015, A1, . Location in patent: Page/Page column
[2] Patent: US2013/190249, 2013, A1, . Location in patent: Page/Page column
[3] Patent: US2015/31627, 2015, A1, . Location in patent: Page/Page column
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YieldReaction ConditionsOperation in experiment
95% With sodium hydroxide In 1,4-dioxane; water; ethyl acetate (36-1)
Synthesis of trans-4-N-t-butyloxycarbonylaminocyclohexanol:
In 90 ml of a mixture of dioxane and water (2:1 by volume) was dissolved 4.7 g of commercially available trans-4-aminocyclohexanol hydrochloride, and 60 ml of 1M sodium hydroxide aqueous solution and 7.9 g of di-t-butyl dicarbonate were added dropwise thereto under ice-cooling over a period of 10 minutes.
Then, after stirring the mixture for 2 hours at room temperature, the reaction mixture was concentrated under reduced pressure to about 1/3 of the original volume on a water both at an external temperature of from 50° to 60° C.
The reaction mixture was extracted three times each time with 30 ml of ethyl acetate, and the organic layer was washed with 30 ml of purified water and 30 ml of a saturated aqueous sodium chloride solution, and, after drying with magnesium sulfate, the solvent was distilled off under reduced pressure.
The thus obtained crude crystals was recrystallized from ethyl acetate to provide 6.15 g (yield 95percent) of colorless acicular trans-4-N-t-butyloxycarbonylaminoaminocyclohexanol.
Reference: [1] Patent: US5166403, 1992, A,
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YieldReaction ConditionsOperation in experiment
91% With sodium hydrogencarbonate In acetonitrile A.
4-(N-Boc-amino)-1-cyclohexanol
To a stirred solution of 4-aminocyclohexan-1-ol (5.00 g, 43.4 mmol) in sat. aq. NaHCO3 (40 ml) was added (Boc)2 O (9.47 g, 43.4 mmol) in CH3 CN (20 ml) at ice-bath cooling.
The reaction mixture was stirred at room temperature for 24 h.
Diluted with water (100 ml), the mixture was extracted with AcOEt (100 ml*4).
The combined extracts were washed with brine, dried and concentrated in vacuo to afford a white crystalline solid (8.46 g, 91percent yield).
1 H-NMR (CDCl3): δ4.44-4.22 (m, 1H), 3.68-3.52 (m, 1H), 3.51-3.31 (m, 1H), 2.08-1.89 (m, 4H), 1.44 (s, 9H), 1.50-1.07 (m, 4H).
Reference: [1] Patent: US6156752, 2000, A,
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YieldReaction ConditionsOperation in experiment
97% With triethylamine In tetrahydrofuran; ethyl acetate Example 55
Compound 55:
Preparation of N1-(1H-Benzimidazol-2-ylmethyl)-N1-((S)-5,6,7,8-tetrahydro-quinolin-8-yl)-trans-cyclohexane-14-diamine (Hydrochloride Salt)
To a solution of trans-4-aminocyclohexanol hydrochloride (10.0 g, 65.9 mmol) and triethylamine (18.4 mL, 132.0 mmol) in tetrahydrofuran (132 mL) was added di-tert-butyl dicarbonate (15.31 g, 70.1 mmol).
The mixture was stirred at 25° C. under nitrogen for 17 h at which time ethyl acetate (250 mL) was added.
The solution was washed with water (2*100 mL), dried (Na2SO4) and concentrated to afford (4-Hydroxy-cyclohexyl)-carbamic acid tert-butyl ester as a white solid (13.82 g, 97percent).
1H NMR (CDCl3) δ 1.09-1.25 (m, 2H), 1.31-1.39 (m, 2H), 1.44 (s, 9H), 1.94-2.03 (m, 4H), 3.42 (bs, 1H), 3.56-3.64 (m, 1H), 4.34 (bs, 1H).
Reference: [1] Patent: US2004/19058, 2004, A1,
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Reference: [1] Patent: WO2004/43962, 2004, A1, . Location in patent: Page 37
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Reference: [1] Patent: WO2005/21515, 2005, A2, . Location in patent: Page/Page column 72
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Reference: [1] Patent: US5726172, 1998, A,
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Reference: [1] Patent: US5574044, 1996, A,
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  • [ 195314-59-1 ]
Reference: [1] Patent: WO2017/100662, 2017, A1,
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  • [ 675112-67-1 ]
Reference: [1] Patent: US2013/190249, 2013, A1,
[2] Patent: WO2013/107291, 2013, A1,
[3] Patent: WO2015/10297, 2015, A1,
[4] Patent: WO2013/107405, 2013, A1,
[5] Patent: WO2015/10626, 2015, A1,
[6] Patent: US2015/31627, 2015, A1,
[7] Patent: US2015/87600, 2015, A1,
[8] Patent: TW2017/36341, 2017, A,
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  • [ 675112-67-1 ]
  • [ 675112-69-3 ]
Reference: [1] Patent: WO2013/107291, 2013, A1,
[2] Patent: WO2015/10297, 2015, A1,
[3] Patent: WO2013/107405, 2013, A1,
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Reference: [1] Patent: TW2017/36341, 2017, A,
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  • [ 675112-70-6 ]
Reference: [1] Patent: US2015/87600, 2015, A1,
[2] Patent: TW2017/36341, 2017, A,
[3] Patent: TW2017/36341, 2017, A,
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