Dichloromethane → HCID 70077018, compound

Participants

Reaction Steps

A suspension of 328 mg (1.0 mmol) of 3-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one in 5 ml of methylene chloride was treated under argon with 0.38 ml (2.2 mmol) of N-ethyldiisopropylamine and 317 mg (1.2 mmol) of α,α'-dibromo-o-xylene and stirred at room temperature under argon for 5 hrs. The solution was washed once with 5 ml of water, dried with sodium sulfate, filtered and evaporated. The crude product was purified by chromatography on 30 g of silica gel (methylene chloride/acetone 4:1, then 2:1). The eluates were evaporated and the residue was taken up in 2.5 ml of methanol. The solution was acidified with ethereal hydrochloric acid and the solvent was removed in a vacuum. The residue was taken up in 6 ml of hot methanol; then cooled to about 0° and the white crystals were isolated by suction filtration. There were obtained 150 mg (32%) of 8-fluoro-3-(3-isoindolin-2-ylmethyl-1,2,4-oxadiazol-5-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one hydrochloride (1:1) of m.p. 229°-233° (dec.).

Provenance & Evidence