(1R, 2S)-3-chloro-1H-indole-6-carboxylic acid (2-amino-cyclohexyl)-amide

Base Information

Chemical Name:(1R, 2S)-3-chloro-1H-indole-6-carboxylic acid (2-amino-cyclohexyl)-amide
CAS No.:764659-50-9
Molecular Formula:C₁₅H₁₈ClN₃O
Molecular Weight:291.78
Hs Code.:

Synonyms:(1R, 2S)-3-chloro-1H-indole-6-carboxylic acid (2-amino-cyclohexyl)-amide

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Chemical Property of (1R, 2S)-3-chloro-1H-indole-6-carboxylic acid (2-amino-cyclohexyl)-amide

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Technology Process of (1R, 2S)-3-chloro-1H-indole-6-carboxylic acid (2-amino-cyclohexyl)-amide

There total 7 articles about (1R, 2S)-3-chloro-1H-indole-6-carboxylic acid (2-amino-cyclohexyl)-amide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

: 764659-49-6
(1S,2R)-{2-[(3-chloro-1H-indole-6-carbonyl)-amino]-cyclohexyl}-carbamic acid tert-butyl ester

: 764659-50-9
(1R, 2S)-3-chloro-1H-indole-6-carboxylic acid (2-amino-cyclohexyl)-amide

Guidance literature:: (1S,2R)-{2-[(3-chloro-1H-indole-6-carbonyl)-amino]-cyclohexyl}-carbamic acid tert-butyl ester; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

With sodium carbonate; In water; ethyl acetate;

Reference yield:

: 764659-69-0
tert-butyl [(1S,2S)-2-(benzyloxy)cyclohexyl]carbamate

: 764659-50-9
(1R, 2S)-3-chloro-1H-indole-6-carboxylic acid (2-amino-cyclohexyl)-amide

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / H₂ / Pd-C / ethanol / 6 h / 1292.9 Torr

2: 92 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: NaN₃ / dimethylformamide / 80 °C

4: H₂ / Pd-C / ethanol / 6 h

5: 62 percent / HATU; DIEA / dimethylformamide

6: TFA / CH₂Cl₂

With sodium azide; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2007.06.029

Reference yield:

: 121282-70-0,145166-06-9,477584-30-8
(1S,2S)-2-tert-Butoxycarbonylamino-1-cyclohexanol

: 764659-50-9
(1R, 2S)-3-chloro-1H-indole-6-carboxylic acid (2-amino-cyclohexyl)-amide

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: NaN₃ / dimethylformamide / 80 °C

3: H₂ / Pd-C / ethanol / 6 h

4: 62 percent / HATU; DIEA / dimethylformamide

5: TFA / CH₂Cl₂

With sodium azide; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2007.06.029