HCID 86619751, compound → HCID 11555060, compound

Participants

Reaction Steps

A few drops of concentrated sulfuric acid was added to 6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (2-oxo-2-phenylethyl) amide (0.100 g, 0.194 mmol). This mixture was stirred at ambient temperature over night. The reaction was quenched with ice water, followed by the addition of 2 mL of 5% ammonia solution. The resulting mixture was extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulphate, then concentrated in vacuo. The residue was purified by column chromatography to yield the title compound as a white solid in 82% yield (0.079 g). m.p. 122-125° C. 1H NMR (300 MHz, CDCl3) δ 8.04 (d, J=9.6 Hz, 1H), 7.80-7.71 (m, 3H), 7.49-7.37 (m, 3H), 7.36-7.29 (m, 1H), 7.28-7.19 (m, 1H), 7.1-7.04 (m, 1H), 7.01 (d, J=9.6 Hz, 1H), 4.08-3.96 (1H), 3.93-3.71 (m, 5H), 3.4-3.32 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 166.1 158.8, 158.4, 152.5, 142.3, 129.8, 129.6, 128.9, 128.8, 127.6, 126.8, 125.1, 124.6, 123.4, 122.9, 116.8, 116.6, 114.9, 114.7, 112.4, 46.4, 44.7, 44.4, 41.4. MS (ES+) m/z 498.1 (M+1).

Provenance & Evidence