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

HRID 1258738Notes

Reaction equation

HRID 1258738 reaction equation
[Cl:1][C:2]1[C:9]([NH:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[C:18]([N:22]4[CH2:27][CH2:26][CH:25]([C:28]([F:31])([F:30])[F:29])[CH2:24][CH2:23]4)[C:19]([Cl:21])=[CH:20][C:13]=3[N:12]=2)=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:32])[CH:3]=1>[Ni].C1COCC1>[Cl:1][C:2]1[C:9]([NH:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[C:18]([N:22]4[CH2:27][CH2:26][CH:25]([C:28]([F:29])([F:31])[F:30])[CH2:24][CH2:23]4)[C:19]([Cl:21])=[CH:20][C:13]=3[N:12]=2)=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([F:32])[CH:3]=1

Participants

4

Reactant 1

HCID 866743494-Chloro-5-[5-chloro-1-methyl-6-(4-(trifluoromethyl)piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]-2-fluorobenzonitrile

Product 1

HCID 866743504-Chloro-2-fluoro-5-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzimidazol-2-ylamino]-benzylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The sub-title compound was prepared in analogy to Example 101, step (c) using 4-chloro-5-[5-chloro-1-methyl-6-(4-(trifluoromethyl)piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]-2-fluorobenzonitrile (264 mg; 0.54 mmol), Ra—Ni (3 mg), H2 (5 atm) and THF (30 mL).

Sources & evidence

ORD record
ord-7c978f191d804ea0885a873d5e3c1400
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

Loading…