Sulfuric Acid → HCID 24829959, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-hydroxy-4-(3-trifluoromethyl-phenyl)-piperidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (prepared in Example 65, 100 mg, 0.22 mmol) in acetonitrile (0.16 mL) and glacial acetic acid (0.21 mL) cooled to 0 C was treated dropwise with concentrated sulfuric acid (0.21 mL). The resulting mixture was then allowed to warm to 25° C. After stirring for 2 h, the reaction mixture was diluted with water, neutralized with a saturated sodium bicarbonate solution and extracted with ethyl acetate. The extracts were dried over sodium sulfate, filtered and concentrated in vacuo. High pressure liquid chromatography (acetonitrile/0.1% trifluoroacetic acid/water gradient) followed by lyophilization of the desired fractions afforded 4-acetylamino-4-(3-trifluoromethyl-phenyl)-piperidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (37 mg, 28%) as a white powder; ES-HRMS m/e calcd. for C21H22N6O3SF3 (M+H)+ 495.1421, found 495.1424.

Provenance & Evidence