6-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (2-aminopropyl)amide → HCID 178430324, compound

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Reaction Steps

6-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (2-aminopropyl)amide (0.100 g, 0.229 mmol) was refluxed in POCl3 (3 mL) for 6 hours. The mixture was cooled, concentrated and quenched with 1 N NaOH (3 mL). The brown solution was extracted with dichloromethane. The organic phase was dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to afford the title compound as thick syrup in 55% yield (0.053 g). 1H NMR (300 MHz, CDCl3) 8.10 (d, J=9.6 Hz, 1H), 7.71 (d, J=7.4 Hz, 1H), 7.65-7.50 (m, 2H), 7.34 (d, J=7.4 Hz, 1H), 6.94 (d, J=9.6 Hz, 1H), 4.25-4.12 (m, 1H), 4.10-3.60 (m, 7H), 3.41 (dd, J=7.6, 11.8 Hz, 1H), 3.30 (t, J=5.1 Hz, 2H), 1.30 (d, J=6.3 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ167.6, 160.9, 159.5, 143.2, 134.2, 134.2, 132.4, 129.5, 127.5, 127.2, 127.1, 126.9, 126.9, 126.8, 126.7, 125.4, 121.8, 112.2, 46.3, 44.5, 44.4, 41.2, 21.6. MS (ES+) m/z 419.2 (M+1).

Provenance & Evidence