Water → HCID 137010690, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-(5-cyano-3-thienyl)-1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (111 mg) obtained in Example 73 in DMSO (2 mL) were added sodium hydrogencarbonate (127 mg) and hydroxylamine hydrochloride (84 mg) at room temperature, and the mixture was stirred at 90° C. for 30 min. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To a solution of the residue in THF (2 mL) were added 1,1′-carbonyldiimidazole (73.5 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.068 mL) at room temperature, and the mixture was stirred overnight. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (90 mg).

Provenance & Evidence