Dimethylformamide → (S)-1-(5-dibenzylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

Participants

Reaction Steps

2.47 g (6.7 mmol) of crude (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one, 20 ml of N,N-dimethylformamide, 9 ml (60 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (1,5-5) and 10.26 g (54 mmol) of benzyl bromide were stirred at room temperature overnight and at 50° for 6 hours. The reaction mixture was concentrated and the residue was purified by chromatography on silica gel while eluting with methylene chloride/methanol 19/1. After recrystallization from ethyl acetate and hexane there were obtained 2.16 g (58%) of (S)-1-(5-dibenzylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of m.p. 107°-109°.

Provenance & Evidence