Dimethylamine → 5-Butylidene-3-[4-(3-dimethylaminomethylimidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.27 ml (3.6 mmol) of formalin and 0.33 g (3.6 mmol) of a 50% aqueous dimethylamine solution in 20 ml of acetic acid, a solution of 1.13 g (3.0 mmol) of 5-butylidene-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione in 5 ml of acetic acid was added at 0° C., followed by stirring at 80° C. for 90 minutes. After cooling, the reaction mixture was poured into 50 ml of 50% aqueous sodium hydroxide under ice cooling conditions. The mixture was extracted with chloroform and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, chloroform/methanol=25/1) to yield 0.43 g (33.3%, yellow oily substance) of the desired product.

Provenance & Evidence