4-(Dimethylamino)Benzaldehyde → HCID 178482662, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(1-(2-amino-5-bromo-3-nitropyridin-4-yl)piperidin-4-yl)-N-(thiazol-2-yl)acetamide (0.110 g, 0.25 mmol) and ethanol (6 ml) was added 4-dimethylaminobenzaldehyde (0.049 g, 0.32 mmol) followed by a freshly prepared 1M aqueous solution of Na2S2O4 (1.0 ml, 1.0 mmol). The reaction mixture was stirred at 80° C. for 18 h, then allowed to cool to room temperature and concentrated in vacuo. The residue was absorbed on silica gel, and the free-running powder was placed on a 10 g silica isolute column which was eluted with ethyl acetate/dichloromethane (v/v; 1:1), 3% methanol in ethyl acetate/dichloromethane (v/v; 1:1), 3% methanol in ethyl acetate, and 3% MeOH in chloroform. The title compound was obtained as a solid after trituration with diethyl ether/methanol (0.027 g, 20%);

Provenance & Evidence