Allyl bromide → HCID 53750833, compound

Participants

Reaction Steps

3 g (7.7 mmol) of crude (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-8-trifluoromethyl-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, 50 ml of methylene chloride, 14.2 ml (72 mmol) of N-ethyldiisopropylamine and 5.14 g (3.6 mmol) of allyl bromide were stirred at room temperature overnight and at 40° for 4 hours. The reaction solution was washed three times with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on 390 g of silica gel while eluting with ethyl acetate. There were obtained 1.50 g (41%) of (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-trifluoromethyl-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, which was converted into the dihydrochloride with methanolic hydrochloric acid.

Provenance & Evidence