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

HRID 1258705
Notes
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Reaction equation

HRID 1258705 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]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 12734Diisopropylcarbodiimide2×HCID 679576795-Chloro-2-methylamino-4-(4-(4-trifluoromethylphenyl)piperazin-1-yl)anilineHCID 86646336N-(4-Chloro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide

Product 1

HCID 57336792N-{4-Chloro-3-[5-chloro-1-methyl-6-(4-(4-trifluoromethylphenyl)piperazin-1-yl)-1H-benzimidazol-2-ylamino]-benzyl}-1-trifluoromethyl-cyclopropanamide

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

  1. concentrationwas concentrated
  2. additionDMF (2 mL) was added to the residue
  3. stirringThe mixture was stirred at rt overnight
  4. stirringthe mixture was stirred at rt overnight
  5. concentrationThe mixture was concentrated
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-817d9a7eb9054bb3844d37a50dbd0abf
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08466186B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes