反应详情

3-(5-Piperidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile (50.8 mg, 0.2 mmol) was mixed with 2-(chloromethyl)quinoline monohydrochloride (47.1 mg, 0.22 mmol) and diisopropylethylamine (129.3 mg, 1.0 mmol) in DMF (2 mL) at 80° C. for 20 h. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water and brine, dried with sodium sulfate, purified by column chromatography with 5˜10% ethyl acetate in hexanes to give a colorless sticky oil. This sticky oil was mixed with 1 M HCl in ether (0.4 mL) and triturated with ethyl acetate to give an off-white solid, 45 mg (48%). 1H NMR (CDCl3+DMSO-d6), δ(ppm): 8.92 (d, 1H), 8.70 (d, 1H), 8.16 (m, 3H), 8.07 (d, 1H), 8.00 (t, 1H), 7.84 (m, 2H), 7.63 (m, 1H), 4.64 (m, 3H), 3.30 (m, 1H), 2.86(m, 1H), 2.04–2.38 (m, 2H), 1.57–1.90 (m, 4H).

1. extractionextracted with dichloromethane
2. washThe organic layer was washed with water and brine
3. dry with materialdried with sodium sulfate
4. custompurified by column chromatography with 5˜10% ethyl acetate in hexanes
5. customto give a colorless sticky oil
6. customtriturated with ethyl acetate
7. customto give an off-white solid, 45 mg (48%)