Acetylglycine → (E)-2-acetamido-4'-benzylthio-3'-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]acetanilide dihydrochloride

Participants

Reaction Steps

To a mixture of 58 mg (0.114 mmol) of (E)-4-benzylthio-3-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]aniline dihydrochloride (prepared as described in Example 82), 20 mg (0.171 mmol) of N-acetylglycine and 1-hydroxy-7-azabenzotriazole in 5 ml of dimethylformamide was added 44 mg (0.228 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride. The mixture was stirred for 4 hours. The solvent was removed and the residue was purified by column chromatography eluting with 5-20% methanol/dichloromethane and treated with 0.10 ml of 4M hydrogen chloride in dioxan. The solvent was evaporated and the residue was recrystallised from acetone/methanol/diethyl ether to give 10 mg of (E)-2-acetamido-4′-benzylthio-3′-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]acetanilide dihydrochloride as a yellow solid; MS: m/e 499 (M+).

Provenance & Evidence