Allyl bromide → HCID 22876572, compound

Participants

Reaction Steps

26.6 g (71 mmol) of crude (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, 400 ml of methylene chloride, 85 ml (496 mmol) of N-ethyldiisopropylamine and 34.5 g (285 mmol) of allyl bromide were stirred at room temperature for 20 hours. The reaction solution was washed three times with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on 2 kg of silica gel while eluting with ethyl acetate. The uniform fractions were evaporated and recrystallized from toluene and n-hexane. There were obtained 22.34 g (69%) of (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of m.p. 103°-104°.

Provenance & Evidence