Valeryl chloride → {4-[6-(5-Butyl[1,2,4]oxadiazol-3-YL)pyridazin-3-YL]piperazin-1-YL}-(2-trifluoromethylphenyl)methanone

Participants

Reaction Steps

Following the procedure as described in Example 4, making variations only as required to use valeryl chloride in place of propionyl chloride to react with N-hydroxy-6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxamidine, the title compound was obtained as white crystals in 48% yield (0.110 g). m.p. 175° C. 1H NMR (300 MHz, CDCl3) 7.90 (d, J=9.3 Hz, 1H), 7.75 (d, J=7.6 Hz, 1H), 7.67-7.48 (m, 2H), 7.30 (d, J=7.5 Hz, 1H), 7.00 (d, J=9.3 Hz, 1H), 4.15-3.65 (m, 6H), 3.32 7.30 (t, J=4.9 Hz, 2H), 2.95 (t, J=7.7 Hz, 2H), 1.92-1.75 (m, 2H), 1.48-1.35 (m, 2H), 0.90 (t, J=7.3 Hz, 2H). 13C NMR (75 MHz, CDCl3) δ 167.6, 166.5, 142.0, 134.3, 134.3, 132.3, 129.4, 127.3, 127.2, 127.1, 126.9, 126.8, 126.8, 111.8, 46.4, 44.6, 44.3, 41.2, 28.5, 26.3, 22.1, 13.5. MS (ES+) m/z 461.2 (M+1).

Provenance & Evidence