Formaldehyde → HCID 67278388, compound

Participants

Reaction Steps

To a solution of pyrrolidine (0.0184 mL) in ACOH (0.6 mL) was added paraformaldehyde (7.8 mg), and stirred at ambient temperature for 5 minutes. To the mixture was added 1-[(1S,2R)-2-methylcyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (30 mg), and stirred at 85° C. for 8 hours, then stirred at ambient temperature for 14 hours. AcOH was removed in vacuo, and the residue was diluted with tetrahydrofuran, then basified with saturated aqueous sodium hydrogencarbonate. The mixture was extracted with EtOAc, washed with 10% NaCl solution, and brine, dried over MgSO4, evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol=15:1 to 10:1) to give 1-[(1S,2R)-2-methylcyclohexyl]-8-(1-pyrrolidinylmethyl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (32.7 mg) as a pale yellow amorphous solid.

Provenance & Evidence