Hydrochloric Acid → HCID 44155103, compound

Participants

Reaction Steps

A 25 mL round bottom flask was charged with 0.75 mL of N,N-dimethylformamide, which was evacuated for 5 minutes and purged with nitrogen. To this flask was added ethyl 1-{[(methylsulfonyl)oxy]methyl}-4-oxo-4H-quinolizine-3-carboxylate, potassium carbonate (25 mg, 0.18 mmol), and then morpholine (0.016 mL, 0.18 mmol), which was stirred for 45 minutes. The reaction mixture was charged with 2.5 N NaOH (0.15 mL, 0.36 mmol), which was stirred for 16 hours. The mixture was acidified with 3 N HCl (1 mL) and then reduced in volume under vacuum, providing material, which was purified by reverse phase HPLC to yield the title compound that gave a proton NMR spectrum consistent with theory and a high resolution mass spectrum (ES+) m/z of 289.1205 calculated for M+H+ [C15H16N2O4: 289.1183]: 1H NMR (500 MHz, DMSO-d6) δ 13.76 (bs, CO2H), 9.81 (bs, 1H), 9.44 (s, 1H), 8.66 (m, 1H), 8.54 (m, 1H), 8.21 (m, 1H), 7.74 (t, J=6.8 Hz, 1H), 4.77 (s, 2H), 3.96 (m, 2H), 3.09-3.64 (m, 6H).

Provenance & Evidence