2,2-Difluorocyclopropane-1-carboxylic acid → HCID 86693382, compound

HRID 575346Notes

Reaction equation

HRID 575346 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]2[CH:8]3[CH2:19][CH:10]([C:11]4[CH:16]=[C:15]([F:17])[C:14]([Br:18])=[CH:13][C:12]=4[C:6]2=[N:5][C:4]=1[C:20]([NH2:22])=[O:21])[CH2:9]3.[F:23][C:24]1([F:30])[CH2:26][CH:25]1[C:27](O)=[O:28]>>[Br:18][C:14]1[C:15]([F:17])=[CH:16][C:11]2[CH:10]3[CH2:9][CH:8]([CH2:19]3)[N:7]3[C:3]([CH2:2][NH:1][C:27]([CH:25]4[CH2:26][C:24]4([F:30])[F:23])=[O:28])=[C:4]([C:20]([NH2:22])=[O:21])[N:5]=[C:6]3[C:12]=2[CH:13]=1

Participants

3

Reactant 2

HCID 27828232,2-Difluorocyclopropane-1-carboxylic acidHCID 86693372HCID 86693372, compound

Product 1

HCID 86693382HCID 86693382, compound

Procedure

3-(aminomethyl)-10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide was reacted with 2,2-difluorocyclopropanecarboxylic acid similarly to as described in example 2 with non-critical modifications to afford crude 10-bromo-3-((2,2-difluorocyclopropanecarboxamido)methyl)-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide which was reacted directly with 2-methyl-3-butyne-ol via General Procedure F to afford 14 mg (33%) of 3-[[(2,2-difluorocyclopropanecarbonyl)amino]methyl]-9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6,7,12-tetrahydro-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide M+1=473.2.

Sources & evidence

ORD record
ord-4a16117800214d0782b00800c874e95e
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

Loading…