HCID 69419367, compound → HCID 21073874, compound

Participants

Reaction Steps

A solution of 7-{5-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-pent-1-enyl}-3-methyl-1H-[1,8]naphthyridin-2-one (0.43 g, 0.94 mmol) in THF was added to a slurry of Raney Ni in EtOH. The mixture was hydrogentated for 4 h at 40 psi. The reaction mixture was filtered through a small celite bed and rinsed with CH2Cl2 and mMeOH. The filtrate was concentrated and purified by column chromatography on silica (10% MeOH/EtOAc) to afford the title compound as a pale yellow solid (0.22 g, 51.4%). mp: 157–158° C.; 1H NMR (400 MHz, CDCl3) δ 9.00 (br s, 1H), 7.75 (d, 1H), 7.50 (s, 1H), 7.15 (m, 2H), 7.00–6.90 (m, 2H), 3.10 (br s, 4H), 2.80 (t, 2H), 2.60 (br s, 4H), 2.42–2.38 (m, 2H), 2.20 (s, 3H), 1.82–1.80 (m, 2H), 1.70–1.60 (m, 4H); MS: ES+: 459.01 (M+H)+, 460.97 (Exact mass: 458.16).

Provenance & Evidence