Diisopropylcarbodiimide → N-{4-Chloro-3-[5-cyano-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino}-benzyl]-1-trifluoromethyl-cyclopropanamide

HRID 1258703Notes

Reaction equation

HRID 1258703 reaction equation
[NH2:1][C:2]1[C:3]([NH:20][CH3:21])=[CH:4][C:5]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([F:19])([F:18])[F:17])[CH2:12][CH2:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8].[Cl:22][C:23]1[CH:39]=[CH:38][C:26]([CH2:27][NH:28][C:29]([C:31]2([C:34]([F:37])([F:36])[F:35])[CH2:33][CH2:32]2)=[O:30])=[CH:25][C:24]=1[N:40]=[C:41]=S.CC(C)N=C=NC(C)C>CN(C=O)C>[Cl:22][C:23]1[CH:39]=[CH:38][C:26]([CH2:27][NH:28][C:29]([C:31]2([C:34]([F:37])([F:36])[F:35])[CH2:33][CH2:32]2)=[O:30])=[CH:25][C:24]=1[NH:40][C:41]1[N:20]([CH3:21])[C:3]2[CH:4]=[C:5]([N:10]3[CH2:15][CH2:14][CH:13]([C:16]([F:19])([F:17])[F:18])[CH2:12][CH2:11]3)[C:6]([C:7]#[N:8])=[CH:9][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 679578515-Amino-4-(methylamino)-2-(4-trifluoromethyl-piperidin-1-yl)benzonitrileHCID 86646336N-(4-Chloro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide

Product 1

HCID 60162659N-{4-Chloro-3-[5-cyano-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino}-benzyl]-1-trifluoromethyl-cyclopropanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in analogy to Example 76 using 5-amino-4-(methylamino)-2-(4-trifluoromethyl-piperidin-1-yl)benzonitrile (179 mg, 0.60 mmol), N-(4-chloro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide (200 mg; 0.60 mmol), DIC (76 mg, 0.60 mmol) and DMF (4 mL).

Sources & evidence

ORD record
ord-5ddd0c33a9c143b089a6c87984dbb0b6
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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