Diisopropylcarbodiimide → N-(4-Fluoro-3-chloro-phenyl)-2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-fluoro-1-methyl-1H-benzimidazole-5-carboxylic acid amide

HRID 410112Notes

Reaction equation

HRID 410112 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([NH2:16])[C:13]([NH:17][CH3:18])=[CH:12][C:11]=2[F:19])=[CH:4][C:3]=1[Cl:21].[Cl:22][C:23]1[C:36]([N:37]=[C:38]=S)=[C:35]([Cl:40])[CH:34]=[CH:33][C:24]=1[CH2:25][NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29].CC(C)N=C=NC(C)C>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:10]2[C:11]([F:19])=[CH:12][C:13]3[N:17]([CH3:18])[C:38]([NH:37][C:36]4[C:35]([Cl:40])=[CH:34][CH:33]=[C:24]([CH2:25][NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[C:23]=4[Cl:22])=[N:16][C:14]=3[CH:15]=2)=[O:20])=[CH:4][C:3]=1[Cl:21]

Participants

4

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 56840192N-[(2,4-dichloro-3-isothiocyanatophenyl)methyl]-2,2-dimethylpropanamideHCID 68052224N-(4-Fluoro-3-chloro-phenyl)-2-fluoro-4-methylamino-5-amino-benzoic acid amide

Product 1

HCID 56840612N-(4-Fluoro-3-chloro-phenyl)-2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-fluoro-1-methyl-1H-benzimidazole-5-carboxylic acid amide

Procedure

The title compound is prepared from N-(4-fluoro-3-chloro-phenyl)-2-fluoro-4-methylamino-5-amino-benzoic acid amide and N-(2,4-dichloro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamide with DIC in analogy to examples 7b/7c.

Sources & evidence

ORD record
ord-3261e9c785a74d239015bcf1219ac50c
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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