Triethylamine → HCID 57455398, compound

Participants

Reaction Steps

A solution of ethyl 4-(3-amino[1,5]naphthyridin-4-ylamino)butanoate (2.0 g, 7.3 mmol) in dichloromethane (35 mL) was cooled to 0° C. Butyryl chloride (0.68 mL, 8.0 mmol) was added dropwise over a period of ten minutes, and the reaction was allowed to warm to ambient temperature, stirred for 90 minutes, and concentrated under reduced pressure. Triethylamine (3.0 mL, 22 mmol) and ethanol (35 mL) were added, and the resulting solution was heated at reflux for two days. Pyridine hydrochloride (0.1 equivalents) was added, and the reaction was heated at reflux overnight. The solvent was removed under reduced pressure, and the residue was partitioned between dichloromethane (70 mL) and saturated aqueous sodium bicarbonate (50 mL). The aqueous layer was separated and extracted with dichloromethane (2×25 mL), and the combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 2.43 g of ethyl 4-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]butanoate as a brown oil.

Provenance & Evidence