Isopropylamine → 9-Fluoro-3-(4-fluoro-benzoyl)-1,1-dimethyl-1,2,3,6-tetrahydroazepino-[4,5-b]indole-5-carboxylic acid isopropylamide

HRID 37977Notes

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH:11]([C:27](OCC)=[O:28])[CH2:12][N:13]([C:18](=[O:26])[C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH2:14][C:15]([CH3:17])([CH3:16])[C:5]=3[C:4]=2[CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH:44]([NH2:47])([CH3:46])[CH3:45]>>[CH:44]([NH:47][C:27]([C:11]1[C:6]2[NH:7][C:8]3[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=3[C:5]=2[C:15]([CH3:17])([CH3:16])[CH2:14][N:13]([C:18](=[O:26])[C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[CH:12]=1)=[O:28])([CH3:46])[CH3:45]

Participants

Reactant 3

HCID 6363Isopropylamine

HCID 682631,1'-Carbonyldiimidazole

HCID 68764325HCID 68764325, compound

Product 1

HCID 114419749-Fluoro-3-(4-fluoro-benzoyl)-1,1-dimethyl-1,2,3,6-tetrahydroazepino-[4,5-b]indole-5-carboxylic acid isopropylamide

Procedure

In a similar manner, ethyl 9-fluoro-3-(4-fluorobenzoyl)-1,1-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate was saponified, converted to the corresponding carboxamide using CDI and isopropylamine, and then oxidized to give 9-fluoro-3-(4-fluoro-benzoyl)-1,1-dimethyl-1,2,3,6-tetrahydroazepino-[4,5-b]indole-5-carboxylic acid isopropylamide MS (ESI): 438 (MH+).

Sources & evidence

ORD record: ord-d75be11742c44460aaca8ea222c34c54
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524704B2

Reaction notes

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