Sulfuric Acid → HCID 59011947, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-hydroxy-4-(3-trifluoromethyl-phenyl)-piperidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (prepared as in Example 65, 114 mg, 0.25 mmol) in acetic acid (0.24 mL) was treated with chloroacetonitrile (0.20 mL, 3.10 mmol). The resulting mixture was sonicated in a water bath until all the solid dissolved and then was cooled to 0° C. The reaction was then treated with concentrated sulfuric acid (0.24 mL) at 0° C. Upon complete addition, the reaction was warmed to 25° C. and was stirred at 25° C. for 2 h. At this time, the mixture was diluted with water and was extracted with ethyl acetate. The organics were washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated in vacuo. The resulting material was triturated with diethyl ether to afford 4-(2-chloro-acetylamino)-4-(3-trifluoromethyl-phenyl)-piperidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (88 mg, 67%) as an off-white solid. This material was used without further purification.

Provenance & Evidence