3-(5-Chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino)-4-trifluoromethyl-benzonitrile → 4-Trifluoromethyl-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzylamine

HRID 1258728Notes

Reaction equation

HRID 1258728 reaction equation
[Cl:1][C:2]1[C:24]([N:25]2[CH2:30][CH2:29][CH:28]([C:31]([F:34])([F:33])[F:32])[CH2:27][CH2:26]2)=[CH:23][C:5]2[N:6]([CH3:22])[C:7]([NH:9][C:10]3[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=3[C:18]([F:21])([F:20])[F:19])[C:13]#[N:14])=[N:8][C:4]=2[CH:3]=1>[Ni].C1COCC1>[F:20][C:18]([F:19])([F:21])[C:17]1[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][C:10]=1[NH:9][C:7]1[N:6]([CH3:22])[C:5]2[CH:23]=[C:24]([N:25]3[CH2:30][CH2:29][CH:28]([C:31]([F:33])([F:34])[F:32])[CH2:27][CH2:26]3)[C:2]([Cl:1])=[CH:3][C:4]=2[N:8]=1

Participants

4

Reactant 1

HCID 866743443-(5-Chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino)-4-trifluoromethyl-benzonitrile

Product 1

HCID 866743464-Trifluoromethyl-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino)-4-trifluoromethyl-benzonitrile (1.20 g; 2.39 mmol), Ra—Ni (14 mg; 0.24 mmol) and THF (50 mL) was shaken under H2-atmosphere (5 atm) overnight at rt. The mixture was filtered through celite and the celite pad was washed with THF and EtOAc. Concentration and crystallization from Et2O/PE gave the sub-title compound.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe celite pad was washed with THF and EtOAc
  3. concentrationConcentration and crystallization from Et2O/PE

Sources & evidence

ORD record
ord-d412e53b6bfb49c7aadffc5da7006f28
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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