Ethylenediamine → HCID 67277766, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methyl-1-[(1S,2R)-2-methylcyclohexyl]-6-{[2-(trimethylsilyl)ethoxy]methyl}-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (40 mg) in water (2 mL) was added trifluoroacetic acid (2 mL) and the mixture was stirred 110° C. for 3 hours. The mixture was extracted with chloroform. The extract was washed with saturated aqueous sodium hydrogencarbonate and water, dried over MgSO4, filtrated and evaporated to give a white solid. The solid was dissolved with tetrahydrofuran (2 mL) and saturated potassium carbonate aqueous solution (2 mL) was added. The mixture was stirred for 1 hour. To the mixture was added 1,2-ethanediamine (0.5 mL) and the mixture was stirred for 1 hour. The mixture was extracted with chloroform. The extract was washed with water, dried over MgSO4, filtrated and evaporated. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 95:5) to give 3-methyl-1-[(1S,2R)-2-methylcyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (25 mg) as a white powder.

Provenance & Evidence