Triethylamine → HCID 57860549, compound

Participants

Reaction Steps

To a solution of 4-chloropyridine-2-carboxylic acid (200 mg, 1.3 mmol), methylamine hydrochloride (103 mg, 1.5 mmol), HOBt (205 mg, 1.5 mmol) and triethylamine (0.42 mL, 3.0 mmol) in DMF (3.0 mL) was added WSCD (292 mg, 1.5 mmol) under ice-cooling, and the mixture was stirred at room temperature for 5 hr. The reaction mixture was diluted with saturated sodium hydrogen carbonate solution, and extracted twice with ethyl acetate. The extracts were combined, washed with brine, dried over magnesium sulfate, filtered through aminosilica gel, and the filtrate was concentrated under reduced pressure. The residue was dissolved in DMF (3.0 mL), the compound of Example 77 (300 mg, 0.59 mmol), potassium carbonate (204 mg, 1.5 mmol) and triethylamine (0.082 mL, 0.59 mmol) were added, and the mixture was stirred at 100° C. for 16 hr. The reaction mixture was diluted with saturated sodium hydrogen carbonate solution, and extracted twice with a mixed solvent of ethyl acetate-THF. The extract was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/hexane=40/60-100/0) and recrystallized from ethyl acetate-hexane to give the title compound (40 mg, 11%) as a pale-yellow solid.

Provenance & Evidence