4-Bromoaniline → N-(4-Bromo-phenyl)-2-(2-chloro-5-{[(1-trifluoromethyl-cyclopropanecarbonyl)-amino]-methyl}-phenylamino)-6-methoxy-1-methyl-1H-benzimidazole-5-carboxylic acid amide

HRID 1410222Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2([C:15]([F:18])([F:17])[F:16])[CH2:14][CH2:13]2)=[O:11])=[CH:4][C:3]=1[NH:19][C:20]1[N:24]([CH3:25])[C:23]2[CH:26]=[C:27]([O:33][CH3:34])[C:28]([C:30]([OH:32])=O)=[CH:29][C:22]=2[N:21]=1.[Br:35][C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=1>>[Br:35][C:36]1[CH:42]=[CH:41][C:39]([NH:40][C:30]([C:28]2[C:27]([O:33][CH3:34])=[CH:26][C:23]3[N:24]([CH3:25])[C:20]([NH:19][C:3]4[CH:4]=[C:5]([CH2:8][NH:9][C:10]([C:12]5([C:15]([F:18])([F:17])[F:16])[CH2:14][CH2:13]5)=[O:11])[CH:6]=[CH:7][C:2]=4[Cl:1])=[N:21][C:22]=3[CH:29]=2)=[O:32])=[CH:38][CH:37]=1

Participants

Reactant 2

HCID 78074-Bromoaniline

HCID 595298032-(2-chloro-5-{[(1-trifluoromethyl-cyclopropanecarbonyl)-amino]-methyl}-phenylamino)-6-methoxy-1-methyl-1H-benzimidazole-5-carboxylic acid

Product 1

HCID 46908357N-(4-Bromo-phenyl)-2-(2-chloro-5-{[(1-trifluoromethyl-cyclopropanecarbonyl)-amino]-methyl}-phenylamino)-6-methoxy-1-methyl-1H-benzimidazole-5-carboxylic acid amide

Procedure

The title compound was prepared from 2-(2-chloro-5-{[(1-trifluoromethyl-cyclopropanecarbonyl)-amino]-methyl}-phenylamino)-6-methoxy-1-methyl-1H-benzimidazole-5-carboxylic acid (92 mg; 0.19 mmol) and 4-bromoaniline (33 mg; 0.19 mmol) in accordance with Example 59, step (a). Yield: 73 mg (59%). 400 MHz 1H-NMR (DMSO-d6, ppm) 10.16 (1H, s) 8.40 (1H, t, J=6.0 Hz) 8.25 (1H, s) 7.85-7.81 (1H, m) 7.76-7.68 (3H, m) 7.51-7.46 (2H, m) 7.40 (1H, d, J=8.2 Hz) 7.22-7.17 (1H, m) 6.92-6.86 (1H, m) 4.25 (2H, d, J=6.0 Hz) 3.97 (3H, s) 3.71 (3H, s) 1.37-1.32 (2H, m) 1.23-1.18 (2H, m). MS m/z: 650, 652, 654 [M+H]+.

Sources & evidence

ORD record: ord-f1a64c6444094770bce465fe65a4592e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921405B2

Reaction notes

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