2-Chlorobenzimidazole → HCID 71208992, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one (intermediate D) (40 mg, 0.140 mmol), N,N-diisopropylethylamine (74.0 mg, 100 μL, 0.570 mmol) and 2-chlorobenzimidazole (29 mg, 0.186 mmol) in NMP (500 μL) was heated at 115° C. in a sealed tube overnight. After this time, very little desired product was observed via LC/MS. Additional 2-chlorobenzimidazole (30 mg, 0.196 mmol), N,N-diisopropylethylamine (74.0 mg, 100 μL, 0.570 mmol), and NMP (0.2 mL) were added, and the reaction mixture was transferred to a small microwave tube. The mixture was heated via microwave irradiation at 180° C. for 2 hr. The reaction mixture was concentrated under a stream of nitrogen, and the crude product was purified by preparative reverse-phase HPLC. The product 3-[(1H-Benzoimidazol-2-ylamino)-methyl]-7-chloro-1-phenyl-1H-quinolin-4-one (4 mg, 6.8%) was obtained as an off-white solid. MS calcd. for C23H17ClN4O [(M+H)+] 401.1, obsd. 401.

Provenance & Evidence