Diisopropylcarbodiimide → N-(4-Bromo-phenyl)-2-(2-fluoro-5-{[(1-trifluoromethyl-cyclopropanecarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide

HRID 1410229Notes

Reaction equation

HRID 1410229 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]([C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[N:19]=[C:20]=S.[NH2:22][C:23]1[C:24]([NH:44][CH3:45])=[CH:25][C:26]([O:39][CH2:40][CH:41]([F:43])[F:42])=[C:27]([CH:38]=1)[C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][CH:32]=1)=[O:29].CC(C)N=C=NC(C)C>CN(C=O)C>[Br:37][C:34]1[CH:35]=[CH:36][C:31]([NH:30][C:28]([C:27]2[C:26]([O:39][CH2:40][CH:41]([F:42])[F:43])=[CH:25][C:24]3[N:44]([CH3:45])[C:20]([NH:19][C:3]4[CH:4]=[C:5]([CH2:6][NH:7][C:8]([C:10]5([C:13]([F:16])([F:15])[F:14])[CH2:12][CH2:11]5)=[O:9])[CH:17]=[CH:18][C:2]=4[F:1])=[N:22][C:23]=3[CH:38]=2)=[O:29])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 595298615-amino-N-(4-bromophenyl)-2-(2,2-difluoroethoxy)-4-(methylamino)benzamideHCID 86646337N-(4-Fluoro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide

Product 1

HCID 46908451N-(4-Bromo-phenyl)-2-(2-fluoro-5-{[(1-trifluoromethyl-cyclopropanecarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in accordance with the procedure in Example 72, step (a) using N-(4-fluoro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide (160 mg; 0.50 mmol), 5-amino-N-(4-bromophenyl)-2-(2,2-difluoroethoxy)-4-(methylamino)benzamide (200 mg; 0.50 mmol), DIC (63 mg; 0.50 mmol) and DMF (4 mL). Yield: 25 mg (7%). 400 MHz 1H-NMR (DMSO-d6, ppm) 10.06 (1H, s) 8.61 (1H, s) 8.39 (1H, t, J=5.8 Hz) 7.87-7.81 (1H, m) 7.73-7.65 (3H, m) 7.52-7.48 (2H, m) 7.29-7.26 (1H, m) 7.21-7.14 (1H, m) 6.91-6.86 (1H, m) 6.65-6.36 (1H, m) 4.55-4.46 (2H, m) 4.24 (2H, d, J=5.8 Hz) 3.71 (3H, s) 1.39-1.32 (2H, m) 1.23-1.20 (2H, m). MS m/z: 684, 686 [M+H]+.

Sources & evidence

ORD record
ord-bab7956f65a740bfb1d2422eaff6bdee
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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