benzyl 4-((6-(2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamido)pyridin-3-yl)methyl)piperazine-1-carboxylate → N-(5-(piperazin-1-ylmethyl)pyridin-2-yl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide

Participants

Reaction Steps

To a solution of benzyl 4-((6-(2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamido)pyridin-3-yl)methyl)piperazine-1-carboxylate (106; 280 mg, 0.46 mmol) in methanol (20 mL) was added Pd/C (0.1 g, 5% on carbon). The reaction mixture was stirred under 1 atm of H2 for 12 h and then filtered through a pad of Celite. The filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography (dichloromethane:methanol=5:1) to afford N-(5-(piperazin-1-ylmethyl)pyridin-2-yl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide (Compound 621) (28.0 mg, 13%). MS (ESI) calcd for C25H23F3N6O: 480.19; found: 481 [M+H].

Provenance & Evidence