Sodium borohydride → HCID 21073761, compound
Reaction equation
[O:1]=[C:2]1[CH2:11][C:10]2[C:9]([N:12]3[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]4[N:32]=[C:31]5[C:26]([CH:27]=[CH:28][C:29](=[O:33])[NH:30]5)=[CH:25][CH:24]=4)[CH2:14][CH2:13]3)=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[BH4-].[Na+]>CO>[OH:1][CH:2]1[CH2:11][C:10]2[C:9]([N:12]3[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]4[N:32]=[C:31]5[C:26]([CH:27]=[CH:28][C:29](=[O:33])[NH:30]5)=[CH:25][CH:24]=4)[CH2:16][CH2:17]3)=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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).