Ethyl 5-amino-1H-indole-2-carboxylate → 5-Amino-N-methyl-2,3-dihydro-1H-indole-1-carboxamide

HRID 1619449Notes

Reaction equation

HRID 1619449 reaction equation
COC(C1N(C)C2C(C=1)=CC(N)=CC=2)=O.C(OC(C1N(C)C2C(C=1)=CC(N)=CC=2)=O)C.C(OC([C:37]1[NH:38][C:39]2[C:44]([CH:45]=1)=[CH:43][C:42]([NH2:46])=[CH:41][CH:40]=2)=O)C.[CH3:47][N:48](C)[C:49](C1NC2C(C=1)=CC(N)=CC=2)=[O:50].COC(C1N(C)C2C(C=1)=CC=C(N)C=2)=O>>[CH3:47][NH:48][C:49]([N:38]1[C:39]2[C:44](=[CH:43][C:42]([NH2:46])=[CH:41][CH:40]=2)[CH2:45][CH2:37]1)=[O:50]

Participants

5

Reactant 4

HCID 10726872Ethyl 5-amino-1H-indole-2-carboxylateHCID 57795743HCID 57795743, compoundHCID 69082308HCID 69082308, compoundHCID 86762496HCID 86762496, compound

Product 1

HCID 123219835-Amino-N-methyl-2,3-dihydro-1H-indole-1-carboxamide

Procedure

5-Amino-1-methyl-1H-indole-2-carboxylic acid methyl ester/5-Amino-1-methyl-1H-indole-2-carboxylic acid ethyl ester (5.25) for Example 32, 47: Pharmagene Laboratories Limited Patent: WO2005/80367 A1; 2005/Boehringer Ingelheim (Canada) Ltd. Patent: US2003/236251 A1; 2003) 5-Amino-1H-indole-2-carboxylic acid ethyl ester (5.26) for Examples 6, 8, 10-12, 16, 26, 28, 30, 31, 33-44, 49, 50, 53, 58-61, 63, 65, 67-193, 197-214, 253-258, 260-262, 273-277, 283: Bayer Healthcare AG; WO2008/56768; A2; 2004) 5-Amino-1H-indole-2-carboxylic acid dimethylamide (5.27) for Example 219, 222, 232: Vertex Pharmaceuticals Incorporated Patent: WO2006/10008; A1; 2006) 6-Amino-1-methyl-1H-indole-2-carboxylic acid methyl ester (5.28) for Examples 66, 265, 266-270: Banyu Pharmaceutical Co. Patent: WO2007/29847 A1; 2007

Sources & evidence

ORD record
ord-3659011d311b4854afe4a0697780e4bc
Source dataset
uspto-grants-2014_07
Patent number
US08772305B2

Reaction notes

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