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

HRID 1258698Notes

Reaction equation

HRID 1258698 reaction equation
[Cl:1][C:2]1[CH:18]=[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:19]=[C:20]=S.[Cl:22][C:23]1[C:24]([N:32]2[CH2:37][CH2:36][CH:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:34][CH2:33]2)=[CH:25][C:26]([NH:30][CH3:31])=[C:27]([CH:29]=1)[NH2:28].CC(C)N=C=NC(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:18]=[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:19][C:20]1[N:30]([CH3:31])[C:26]2[CH:25]=[C:24]([N:32]3[CH2:37][CH2:36][CH:35]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH2:34][CH2:33]3)[C:23]([Cl:22])=[CH:29][C:27]=2[N:28]=1

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 679580485-Chloro-2-methylamino-4-(4-phenyl-piperidin-1-yl)anilineHCID 86646336N-(4-Chloro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide

Product 1

HCID 67975182N-{4-Chloro-3-[5-chloro-1-methyl-6-(4-phenyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}-1-trifluoromethyl-cyclopropanamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(4-chloro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide (200 mg; 0.60 mmol) and 5-chloro-2-methylamino-4-(4-phenyl-piperidin-1-yl)aniline (190 mg; 0.60 mmol) in DMF (4 mL) was stirred overnight at rt. DIC (76 mg; 0.60 mmol) was added and the mixture was heated at 90° C. for 1.5 h. The mixture was poured in water, extracted with EtOAc and the combined organic layer was dried over Na2SO4, filtered and concentrated and the residue was purified by column chromatography.

Workup

  1. temperaturethe mixture was heated at 90° C. for 1.5 h
  2. extractionextracted with EtOAc
  3. dry with materialthe combined organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-59e229fb442d43f1a875e770db7f0a24
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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