Diisopropylcarbodiimide → N-(4-Bromo-phenyl)-2-{2,6-difluoro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide

HRID 410102Notes

Reaction equation

HRID 410102 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:24])[C:10]2[CH:15]=[C:14]([NH2:16])[C:13]([NH:17][CH3:18])=[CH:12][C:11]=2[O:19][CH2:20][CH:21]([F:23])[F:22])=[CH:4][CH:3]=1.[F:25][C:26]1[C:39]([N:40]=[C:41]=S)=[C:38]([F:43])[CH:37]=[CH:36][C:27]=1[CH2:28][NH:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32].CC(C)N=C=NC(C)C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:10]2[C:11]([O:19][CH2:20][CH:21]([F:22])[F:23])=[CH:12][C:13]3[N:17]([CH3:18])[C:41]([NH:40][C:39]4[C:38]([F:43])=[CH:37][CH:36]=[C:27]([CH2:28][NH:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[C:26]=4[F:25])=[N:16][C:14]=3[CH:15]=2)=[O:24])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 56840193N-(2,4-Difluoro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamideHCID 595298615-amino-N-(4-bromophenyl)-2-(2,2-difluoroethoxy)-4-(methylamino)benzamide

Product 1

HCID 56839973N-(4-Bromo-phenyl)-2-{2,6-difluoro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide

Procedure

The title compound is prepared from N-(4-bromophenyl)-2-(2,2-difluoro-ethoxy)-4-methylamino-5-amino-benzamide and N-(2,4-difluoro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamide with DIC in analogy to example 1g.

Sources & evidence

ORD record
ord-66e56a629ed34b0bb6bf0dc0bce8ae35
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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