Potassium Carbonate → HCID 68664101, compound

Participants

Reaction Steps

To a solution of 4-[5-[(3-fluorobenzyl)thio]-1,3,4-oxadiazol-2-yl]pyridin-2-amine (408 mg, 1.35 mmol) and triethylamine (0.468 mL) in tetrahydrofuran (20 mL) was added 2,2,2-trichloroethyl chloroformate (0.558 mL, 4.05 mmol) under ice-cooling, and the resulting mixture was stirred for 30 min. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/10), and the obtained compound was dissolved in N,N-dimethylformamide (15 mL). To this solution were added potassium carbonate (383 mg, 2.77 mmol), water (3 mL) and 2-(aminomethyl)pyridine (300 mg, 2.77 mmol) under ice-cooling, and the resulting mixture was stirred at room temperature for 30 min and at 50° C. for 30 min. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/10, ethyl acetate/methanol=9/1), and recrystallized from diethyl ether/methanol to give the title compound (313 mg, yield 57%) as colorless crystals.

Provenance & Evidence