1H-indole-6-carboxylic acid → HCID 71208741, compound

HRID 1887934Notes

Reaction equation

HRID 1887934 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[C:13](=[O:14])[C:12]2[C:7](=[N:8][C:9]([C:15]([F:18])([F:17])[F:16])=[CH:10][CH:11]=2)[N:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]=1[C:25]([O:27][CH3:28])=[O:26].[NH:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C:38](O)=[O:39])[CH:36]=2)[CH:31]=[CH:30]1>>[CH3:28][O:27][C:25]([C:5]1[N:6]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:7]2[C:12]([C:13](=[O:14])[C:4]=1[CH2:3][NH:2][C:38]([C:35]1[CH:36]=[C:37]3[C:32]([CH:31]=[CH:30][NH:29]3)=[CH:33][CH:34]=1)=[O:39])=[CH:11][CH:10]=[C:9]([C:15]([F:16])([F:17])[F:18])[N:8]=2)=[O:26]

Participants

3

Reactant 2

HCID 5952301H-indole-6-carboxylic acidHCID 712084273-Aminomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester hydrochloride

Product 1

HCID 71208741HCID 71208741, compound

Procedure

3-{[(1H-Indole-6-carbonyl)-amino]-methyl}-4-oxo-1-phenyl-7-trifluoromethyl-1,4-di-hydro-[1,8]naphthyridine-2-carboxylic acid methyl ester was prepared starting from intermediate J and 1H-indole-6-carboxylic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 11.35 (br. s., 1H) 8.90 (d, J=8.15 Hz, 1H) 8.36 (br. s., 1H) 7.96 (d, J=8.15 Hz, 1H) 7.89 (s, 1H) 7.37-7.59 (m, 8 H) 6.46 (br. s., 1H) 4.47 (d, J=4.83 Hz, 2H) 3.37 (s, 3H) MS calcd. for C27H19F3N4O4 [(M+H)+] 521.1 obsd. 521.0.

Sources & evidence

ORD record
ord-24275aff55774b269285e4185771ea62
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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