Piperidine → HCID 71208726, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one (intermediate D) (30 mg, 0.105 mmol) and N,N-diisopropylethylamine (40.9 mg, 55.2 μL, 0.316 mmol) in NMP (500 μL) was added 4,6-dichloropyrimidine (15.7 mg, 0.105 mmol). The mixture was warmed to 120° C. in a sealed microwave tube. After 1.5 hr, piperidine (35.9 mg, 41.7 μL, 0.421 mmol) was added and heating at 120° C. continued for 9 hr. The reaction mixture was cooled to room temperature. The crude product was purified by preparative reverse-phase HPLC, giving 7-chloro-1-phenyl-3-[(6-piperidin-1-yl-pyrimidin-4-ylamino)-methyl]-1H-quinolin-4-one (25 mg, 53%) as an off-white solid. MS calcd. for C25H24ClN5O [(M+H)+] 446, obsd. 446.

Provenance & Evidence