Triethylamine → 4-(6-Acetoxyacetylaminomethylpyridin-2-yl)-2-[(acetoxyacetylamino)(amino)methyleneamino]thiazole

Participants

Reaction Steps

Acetoxyacetyl chloride (0.7 g) was added to a mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride (1.5 g) and triethylamine (2.6 ml) in dichloromethane (30 ml) under ice-cooling and the mixture was stirred at ambient temperature for 20 hours. The reaction mixture was added to a mixture of tetrahydrofuran, ethyl acetate and water and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was separated and purified by column chromatograpy on silica gel, and eluted with a mixture of chloroform and methanol (9:1, V/V). The eluted fast fractions containing the desired were collected and evaporated in vacuo to give 4-(6-acetoxyacetylaminomethylpyridin-2-yl)-2-[(acetoxyacetylamino)(amino)methyleneamino]thiazole (0.3 g).

Provenance & Evidence