Ethyl orthoformate → HCID 69192155, compound

Participants

Reaction Steps

Triethyl orthoformate (1.86 mL, 17.0 mmol) and pyridine hydrochloride (0.164 g, 1.42 mrnmol) were added to a stirred suspension of 3-[(3-amino[1,5]naphthyridin-4-yl)amino]propyl acetate (prepared as described in Part C of Examples 127-135, 3.70 g, 14.2 mmol) in toluene (70 mL). The mixture was heated at reflux with a Dean-Stark trap. After 2.5 hours, additional triethyl orthoformate (1 mL) was added and heating was continued for another 2 hours. The mixture was allowed to cool to room temperature and was concentrated under reduced pressure to afford a dark oil that was dissolved in dichloromethane (100 mL). The solution was washed with saturated aqueous sodium bicarbonate (50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 3.50 g of 3-(1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propyl acetate as an orange oil that was used without further purification in the next step.

Provenance & Evidence