Potassium Carbonate → HCID 57886922, compound

Participants

Reaction Conditions

Reaction Steps

4-Methoxybenzyl isocyanate (0.5 ml) and potassium carbonate (486 mg) were added to a solution of ethyl 3-amino-5-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chloro-5-fluorobenzyl)-4-cyano-1H-pyrrole-2-carboxylate (920 mg) in pyridine (1 ml), and the resulting mixture was stirred at 130° C. for 6 hours. 4-Methoxybenzyl isocyanate (2.0 ml) was added thereto, followed by stirring with heating for another 24 hours. The reaction solution was cooled to 25° C. and then concentrated under reduced pressure and water was added to the residue, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (15 ml), followed by adding thereto potassium carbonate (486 mg) and methyl iodide (0.33 ml), and the resulting mixture was stirred at 25° C. for 3 hours. A saturated aqueous ammonium chloride solution was added to the reaction solution, followed by extraction with chloroform. The organic layer was washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (750 mg) as a light-yellow amorphous substance.

Provenance & Evidence