反应详情

To a solution of 7-{4-[4-(7-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl)-piperazin-1-yl]-butoxy}-1H-[1,8]naphthyridin-2-one (1.20 g, 2.69 mmol) in methanol (10 mL) was added portionwise NaBH4 (0.41 g, 10.76 mmol). The reaction mixture was stirred at room temperature for 30 min and quenched with saturated NH4Cl solution and the compound was extracted with CH2Cl2 (2×20 mL). The organic layer was washed with brine (20 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude product was purified by column chromatography (10% methanol in ethyl acetate) to afford the title compound (0.60 g, 50%), as a white solid. 1H NMR (400 MHz, CDCl3) δ 9.25 (s, 1H), 7.72 (d, 1H), 7.63 (d, 1H), 7.12 (t, 1H), 6.91 (d, 1H), 6.85 (d, 1H), 6.59 (d, 1H), 6.52 (d, 1H), 4.23 (t, 2H), 4.13–4.08 (m, 1H), 3.25–3.20 (m, 1H), 3.02–2.83 (m, 6H), 2.61–2.47 (m 6H), 1.88–1.71 (m, 6H). ES MS: 449.26 (M+1)+ (Exact mass: 448.25).

1. customquenched with saturated NH4Cl solution
2. extractionthe compound was extracted with CH2Cl2 (2×20 mL)
3. washThe organic layer was washed with brine (20 mL)
4. dry with materialdried over anhydrous Na2SO4
5. filtrationfiltered
6. customevaporated
7. customThe crude product was purified by column chromatography (10% methanol in ethyl acetate)