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

HRID 1258745Notes

Reaction equation

HRID 1258745 reaction equation
[Cl:1][C:2]1[C:18]([F:19])=[CH:17][C:5]([CH2:6][NH:7][C:8]([C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[N:20]=[C:21]=S.[Cl:23][C:24]1[C:25]([N:33]2[CH2:38][CH2:37][CH:36]([C:39]([F:42])([F:41])[F:40])[CH2:35][CH2:34]2)=[CH:26][C:27]([NH:31][CH3:32])=[C:28]([CH:30]=1)[NH2:29].CC(C)N=C=NC(C)C>CN(C=O)C>[Cl:1][C:2]1[C:18]([F:19])=[CH:17][C:5]([CH2:6][NH:7][C:8]([C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[NH:20][C:21]1[N:31]([CH3:32])[C:27]2[CH:26]=[C:25]([N:33]3[CH2:38][CH2:37][CH:36]([C:39]([F:41])([F:42])[F:40])[CH2:35][CH2:34]3)[C:24]([Cl:23])=[CH:30][C:28]=2[N:29]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 679581715-Chloro-2-methylamino-4-(4-trifluoromethyl-piperidin-1-yl)anilineHCID 86674353N-(4-chloro-5-fluoro-3-isothiocyanatobenzyl)-1-trifluoromethyl-cyclopropane carboxamide

Product 1

HCID 86674352N-{4-Chloro-5-fluoro-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 the procedure in Example 76 using N-(4-chloro-5-fluoro-3-isothiocyanatobenzyl)-1-trifluoromethyl-cyclopropane carboxamide (211 mg; 0.60 mmol), 5-chloro-2-methylamino-4-(4-trifluoromethyl-piperidin-1-yl)aniline (184 mg; 0.60 mmol), DIC (78 mg; 0.60 mmol) and DMF (4 mL).

Sources & evidence

ORD record
ord-bbce8c89c161482eb979aac196c160aa
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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