HCID 86653283, compound → HCID 44156855, compound

Participants

Reaction Steps

To a solution of ethyl 4-oxo-1-{[4-(2-vinylpyridin-4-yl)piperazine-1-yl]methyl}-4H-quinolizine-3-carboxylate (0.050 g, 0.12 mmol) in 3 mL of MeOH under nitrogen was added Pd/C (10 mol %). The reaction was placed under an atmosphere of hydrogen (balloon). After 2 hours, the mixture was filtered and concentrated in vacuo. To a solution of the resulting residue in 1 mL of DMSO was added aqueous lithium hydroxide (0.3 mL). After 2 hours, the reaction mixture was acidified with 6 N HCl to pH ˜2, filtered, and subjected to purification via reverse phase HPLC to provide the title compound which gave a proton NMR consistent with theory and a mass ion (ES+) of 393.1 for M+H+ [C22H24N4O3: 392.45]: 1H NMR (400 MHz, DMSO-d6) δ 9.43 (d, J=7.0 Hz, 1H), 8.56 (s, 1H), 8.51 (d, J=9.0 Hz, 1H), 8.26 (d, J=6.6 Hz, 1H), 8.18 (t, J=7.4 Hz, 1H), 7.16-7.14 (m, 2H), 4.67-3.17 (m, 10H), 2.76 (q, J=7.5 Hz, 2H), 1.26 (q, J=7.5 Hz, 1H).

Provenance & Evidence