Sodium triacetoxyborohydride → 7-{4-[4-(5-Chloro-2-isopropoxy-phenyl)-piperazin-1-yl]-butoxy}-1H-[1,8]naphthyridin-2-one

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To a suspension of 4-(7-oxo-7,8-dihydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (0.206 g, 0.887 mmol, 1 eq) and 1-(5-chloro-2-isopropoxy-phenyl)-piperazine (0.328 g, 0.977 mmol, 1.1 eq) in dichloroethane (5 mL) was added NaBH(OAc)3 (0.535 g, 2.524 mmol, 2.84 eq). The slurry was allowed to stir overnight at room temperature (18 h). Analysis by HPLC showed reaction mostly complete. The mixture was diluted with Ethyl Acetate and quenched with saturated NaHCO3. The organic phase was washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. Purification by silica gel chromatography (2% MeOH/CH2Cl2) followed by formation of the HCl salt using 1N HCl in ether provided the title compound (0.164 g, 39%). MS: APCI: M+1: 471.2 (Exact Mass: 470.21).

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