o-Bis(bromomethyl)benzene → 7-chloro-5,6-dihydro-3-(3-isoindolin-2-yl-methyl-1,2,4-oxadiazol-5-yl)-5-methyl-4H-imidazo[1,5-a][1,4]-benzodiazepin-6-one

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Reaction Steps

3.44 g (10 mmol) of 3-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-7-chloro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one, 30 ml of N,N-dimethylformamide, 3.7 ml (22 mmol) of N-ethyldiisopropylamine and 2.9 g (11 mmol) of α,α'-dibromo-o-xylene were stirred at room temperature for 6 hours. After evaporating the solvent the residue was chromatographed on 230 g of silica gel while eluting with ethyl acetate. The uniform fractions were evaporated. There were obtained 1.56 g (35%) of 7-chloro-5,6-dihydro-3-(3-isoindolin-2-yl-methyl-1,2,4-oxadiazol-5-yl)-5-methyl-4H-imidazo[1,5-a][1,4]-benzodiazepin-6-one, which was converted into the hydrochloride of m.p. 180°-184°.

Provenance & Evidence