Water → HCID 178482332, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6,7-diamino-1-[(1S,2R)-2-methylcyclohexyl]-1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one (147 mg) in toluene-ethanol (1 mL-0.5 mL) was added methyl isothiocyanate (43 μL). The resulting solution was heated for 80° C. for 1 hour. After cooling to ambient temperature, the reaction mixture was added drop wise water. The mixture was extracted with EtOAc (2×15 mL). The combined extracts were washed with brine (20 mL), dried over MgSO4. Removal of the solvent preceded the crude thiocarbamate which was used in the next step with out purification. To a solution of above carbamate in toluene (1 mL) was added WSCD HCl (162 mg) at ambient temperature. The mixture was heated at 110° C. for 1 hour. After cooling to ambient temperature, the reaction mixture was diluted with EtOAc (20 mL), and washed with saturated aqueous sodium hydrogencarbonate (20 mL) and brine (20 mL). The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography (silica gel chloroform:methanol=90:10) to give 2-(methylamino)-8-[(1S,2R)-2-methylcyclohexyl]-6,8-dihydrodiimidazo[4,5-b:4′,5′-d]pyridin-7(3H)-one (10 mg) as a pale yellow solid.

Provenance & Evidence