Diisopropylcarbodiimide → N-{4-Chloro-3-[5,7-difluoro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}-1-trifluoromethyl-cyclopropanamide

HRID 1258709Notes

Reaction equation

HRID 1258709 reaction equation
[F:1][C:2]1[C:3]([NH:20][CH3:21])=[C:4]([CH:6]=[C:7]([F:19])[C:8]=1[N:9]1[CH2:14][CH2:13][CH:12]([C:15]([F:18])([F:17])[F:16])[CH2:11][CH2:10]1)[NH2:5].[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[C:2]([F:1])=[C:8]([N:9]3[CH2:14][CH2:13][CH:12]([C:15]([F:16])([F:18])[F:17])[CH2:11][CH2:10]3)[C:7]([F:19])=[CH:6][C:4]=2[N:5]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 86646336N-(4-Chloro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamideHCID 866743403,5-Difluoro-2-methylamino-4-(4-trifluoromethyl-piperidin-1-yl)aniline

Product 1

HCID 60162014N-{4-Chloro-3-[5,7-difluoro-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 3,5-difluoro-2-methylamino-4-(4-trifluoromethyl-piperidin-1-yl)aniline (186 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 (3 mL).

Sources & evidence

ORD record
ord-7b130626cf6a47e08d32bd055a0d8190
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

Loading…