Acetyl isothiocyanate → 4-(3-Acetylthioureido)-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

Participants

Reaction Steps

To a solution of 4-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 1J, 60 mg, 0.177 mmol) in acetone (1.182 mL) was added acetyl isothiocyanate (0.020 mL, 0.230 mmol). The reaction mixture was stirred at room temperature for 6 h. LC/MS showed still half of the starting material left. Another 0.5 equivalent of acetyl isothiocyanate was added and the reaction mixture was heated at 35° C. overnight. Solvent was evaporated and the crude product was purified by flash chromatography on silica gel using an automated ISCO system (24 g column, eluting with 2-8% methanol/dichloromethane). 4-(3-Acetylthioureido)-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (34 mg, 43.6% yield) was obtained as a yellow solid.

Provenance & Evidence