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

HRID 1258726Notes

Reaction equation

HRID 1258726 reaction equation
[Cl:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]([F:20])([F:19])[F:18])[CH2:13][CH2:12]2)=[CH:4][C:5]([NH:9][CH3:10])=[C:6]([CH:8]=1)[NH2:7].[F:21][C:22]([F:44])([F:43])[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>[F:21][C:22]([F:44])([F:43])[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:9]([CH3:10])[C:5]2[CH:4]=[C:3]([N:11]3[CH2:16][CH2:15][CH:14]([C:17]([F:19])([F:20])[F:18])[CH2:13][CH2:12]3)[C:2]([Cl:1])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 679581715-Chloro-2-methylamino-4-(4-trifluoromethyl-piperidin-1-yl)anilineHCID 86646341N-(4-trifluoromethyl-3-isothiocyanato-benzyl)-1-(trifluoromethyl)cyclopropane carboxamide

Product 1

HCID 86674343N-{4-Trifluoromethyl-3-[5-chloro-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-chloro-2-methylamino-4-(4-trifluoromethyl-piperidin-1-yl)aniline (185 mg, 0.60 mmol), N-(4-trifluoromethyl-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide (221 mg, 0.60 mmol), DIC (76 mg, 0.60 mmol) and DMF (4 mL).

Sources & evidence

ORD record
ord-65d2425f22ad44b5bcc7c4d05874a0bb
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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