Diisopropylcarbodiimide → N-{4-Chloro-3-[5-chloro-1-methyl-6-(4-(4-trifluoromethylphenyl)piperazin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}-1-trifluoromethyl-cyclopropanamide
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][N:35]([C:38]3[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[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>>[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][N:35]([C:38]4[CH:39]=[CH:40][C:41]([C:44]([F:45])([F:47])[F:46])=[CH:42][CH:43]=4)[CH2:34][CH2:33]3)[C:23]([Cl:22])=[CH:29][C:27]=2[N:28]=1Participants
4
Reactant 3
Product 1
Procedure
N-(4-Chloro-3-isothiocyanatobenzyl)-1-trifluoromethyl-cyclopropane carboxamide (161 mg, 0.48 mmol) was added to the THF solution from step (a) above and the mixture was concentrated. DMF (2 mL) was added to the residue, the mixture was stirred at rt for 1 h and DIC (67 mg, 0.53 mmol) was added. The mixture was stirred at rt overnight, another portion of DIC (17 mg, 0.13 mmol) was added and the mixture was stirred at rt overnight. The mixture was concentrated and the residue was purified by column chromatography to give the title compound.
Workup
- concentrationwas concentrated
- additionDMF (2 mL) was added to the residue
- stirringThe mixture was stirred at rt overnight
- stirringthe mixture was stirred at rt overnight
- concentrationThe mixture was concentrated
- customthe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-817d9a7eb9054bb3844d37a50dbd0abf
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466186B2
Reaction notes
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