N,N'-Dimethylethylenediamine → HCID 44155101, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 1-{[2-(3-fluorophenyl)-3-oxopiperazin-1-yl]methyl}-4-oxo-4 H-quinolizine-3-carboxylate (0.100 g, 0.236 mmol), phenyliodide (48.2 mg, 0.236 mmol), N,N′-dimethylethylenediamine (4.5 mg, 0.051 mmol), copper (I) iodide (4.5 mg, 0.024 mmol), and 1 N cesium carbonate (0.59 mL, 0.59 mmol) was heated under nitrogen to 100° C. for 18 hours. The reaction was then cooled to room temperature and concentrated in vacuo. The resultant residue was redissolved in 1 mL DMSO, and saturated aqueous LiOH (0.3 mL) was added. After 2 hours, the mixture was acidified with 6 N HCl to pH ˜3, filtered, and purified by reverse phase HPLC to provide the title compound which gave a proton NMR consistent with theory and a mass ion (ES+) of 471.9 for M+H+ [C27H22FN3O4: 471.48]: 1H NMR (400 MHz, DMSO-d6) δ 9.38 (d, J=7.2 Hz, 1H), 8.42 (s, 1H), 7.98-7.92 (m, 2H), 7.61-7.58 (m, 1H), 7.58-7.39 (m, 2H), 7.39-7.29 (m, 5H), 7.19 (d, J=9.8 Hz, 1H), 7.01-6.97 (m, 1H), 3.99 (s, 1H), 3.98-3.96 (m, 2H), 3.86 (d, J=13.5 Hz, 1H), 3.68-3.64 (m, 1H), 3.24-3.20 (m, 1H), 3.00-2.93 (m, 1H).

Provenance & Evidence