Allyl bromide → HCID 54032652, compound

Participants

Reaction Steps

5.02 g (14 mmol) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, 75 ml of N,N-dimethylformamide, 21 g (173.8 mmol) of allyl bromide and 29.4 g (193 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (1,5-5) were stirred at 75° for 60 hours. The solution was concentrated and the residue was purified by chromatography on 350 g of silica gel while eluting with ethyl acetate. There were obtained 1.97 g (35%) of (S)-1-(3-diallylaminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, which was converted into the hydrochloride of m.p. 190°-192°.

Provenance & Evidence