Ammonium Chloride → HCID 86649996, compound

Participants

Reaction Conditions

Reaction Steps

Sodium borohydride (1.009 g, 26.66 mmol) was suspended in a mixture of tetrahydrofuran (36 ml) and water (9 ml), and the suspension was cooled to −20° C. A suspension of N-(4-{2-[2,3-difluoro-4-(1H-imidazol-1-ylcarbonyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (503.5 mg, 1.338 mmol) in anhydrous tetrahydrofuran (4 ml) was added dropwise. After stirring at not more than 0° C. for 2.5 hr, saturated aqueous ammonium chloride (50 ml) was added. The mixture was extracted 3 times with ethyl acetate, and the combined organic layer was washed with saturated aqueous ammonium chloride and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue were added methanol (0.5 ml) and diisopropyl ether (25 ml), and the mixture was stirred and filtered. The filtered product was dried under reduced pressure to give N-(4-{2-[2,3-difluoro-4-(hydroxymethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (316.8 mg, 1.014 mmol, 75.8%) as a white solid.

Provenance & Evidence