N'-Hydroxycyclopropanecarboximidamide → HCID 21289948, compound

Participants

Reaction Steps

6.2 g (18 mmol) of 7-bromo-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid in 90 ml of N,N-dimethylformamide are stirred at 70° for 2.5 hours with 2.92 g (18 mmol) of N,N'-carbonyldiimidazole. 1.80 g (18 mmol) of cyclopropanecarboxamidoxime are subsequently added thereto and the mixture is stirred at 100° for a further 2 hours. The solution is evaporated, the residue is treated with 70 ml of acetic acid and the mixture is stirred at 120° for 5 hours. The reaction mixture is evaporated and the residue is partitioned between methylene chloride and saturated sodium bicarbonate solution. The organic phase is dried over magnesium sulphate and evaporated. By chromatography on silica gel while eluting with ethyl acetate and recrystallization from acetonitrile there is obtained 7-bromo-4,5-dihydro-3-(3-cyclopropyl-1,2,4-oxadiazol-5yl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 187°-189°.

Provenance & Evidence