Triethylamine → 6-Chloro-7-[4-(4-naphthalen-1-yl-piperazin-1-yl)-butoxy]-3,4-dihydro-1H-[1,8]naphthyridin-2-one

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Reaction Steps

To a solution of 4-(3-chloro-7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (400 mg, approx. 1.49 mmol, crude from previous reaction) in DCE (7 mL) was added 1-naphthalen-1-yl-piperazine hydrochloride (370 mg, 1.49 mmol) followed by Et3N (0.42 mL, 2.98 mmol). The solution was stirred for 15 min and NaBH(OAc)3 (410 mg, 1.94 mmol) was added as a powder. The reaction was stirred at room temperature for 2 h and quenched with saturated NaHCO3 and H2O. The mixture was extracted with EtOAc. The organic layer was washed with saturated NaHCO3, H2O and brine, dried over Na2SO4 and concentrated. Purification by liquid chromatography (0–3% MeOH/CH2Cl2) afforded the title compound as an off-white foam (324 mg, 0.697 mmol, 47%). Et2O was added and the foam turned into a white solid after 5 minutes of stirring. The solid was collected by filtration, washed with Et2O and dried to give a white solid. MS: APCI: M+1: 465.2 (Exact Mass: 464.20).

Provenance & Evidence