2-Chlorobenzimidazole → N-(Benzimidazol-2-yl)-4,4'-difluorobenzhydrylamine

HRID 16554Notes

Reaction equation

HRID 16554 reaction equation
Cl[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[F:11][C:12]1[CH:26]=[CH:25][C:15]([CH:16]([NH2:24])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[CH:14][CH:13]=1>>[N:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[NH:3][C:2]=1[NH:24][CH:16]([C:15]1[CH:25]=[CH:26][C:12]([F:11])=[CH:13][CH:14]=1)[C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 785722-ChlorobenzimidazoleHCID 109550394-Fluoro-alpha-(4-fluorophenyl)benzenemethanamine

Product 1

HCID 11624170N-(Benzimidazol-2-yl)-4,4'-difluorobenzhydrylamine

Procedure

The title compound was prepared from 2-chlorobenzimidazole and 4,4′-difluoro-benzhydrylamine (prepared by Procedure B from 4,4′-difluorobenzophenone) by Procedure A. The product was isolated by preparative LCMS to give the title compound as the free base (white solid, mp 241-243° C.). MS(ES+) m/z 336 ([M+1]+, 100). 1NMR (DMSO-d6) δ 6.20 (d, 1H), 6.80-6.91 (m, 2H), 7.09-7.20 (m, 6H), 7.38-7.43 (m, 4H), 7.69 (d, 1H), 10.6 (s, 1H).

Workup

  1. customThe product was isolated by preparative LCMS

Sources & evidence

ORD record
ord-717e1b432dec4e4b906aaebcf91b3a05
Source dataset
uspto-grants-2010_06
Patent number
US07737167B2

Reaction notes

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