Triethylamine → HCID 11654830, compound

Participants

Reaction Steps

To a mixture of 4-(7-oxo-7,8-dihydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (175 mg, 0.754 mmol) and 1-naphthalen-1-yl-piperazine hydrochloride (206 mg, 0.829 mmol) in DCE (4 mL) was added Et3N (0.23 mL, 1.66 mmol). The mixture was stirred for 10 min and NaBH(OAc)3 (224 mg, 1.06 mmol) was added as a powder. The reaction was stirred at room temperature for 2 h and then quenched with saturated NaHCO3. The mixture was extracted with EtOAc. The organic layer was washed with saturated NaHCO3 and brine, dried over Na2SO4 and concentrated to give a white foam. Purification by liquid chromatography (5% MeOH/CH2Cl2) gave the title compound as a white foam (260 mg, 0.607 mmol, 80%). The foam was dissolved in a minimal amount of CH2Cl2 and Et2O was added. 1M HCl in Et2O (0.6 mL) was added and a white precipitate formed. The solid was collected by filtration, washed with Et2O and dried to give a white fluffy solid (257 mg). MS: APCI: M+1: 429.2 (Exact Mass: 428.22).

Provenance & Evidence