反应详情

To a 0° C. suspension of 9-chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide (50 mg, 0.11 mmol) in ethanol (5 mL) add 1,8-diazabicyclo[5.4.0]undec-7-ene (42 μL, 0.28 mmol). Stir the solution for 10 mins. To the solution add α-toluene-sulfonyl chloride (21 mg, 0.11 mmol) and stir the reaction at 0° C. under nitrogen for 30 minutes. Quench the reaction with 1N HCl, concentrate, and extract with 20% isopropanol/chloroform (×2). Wash the combined organic layers with saturated aqueous sodium bicarbonate solution, brine, dry over magnesium sulfate and concentrate. Purify by flash chromatography on silica gel (eluting with 0–0.4% methanol/chloroform) to give 37.9 mg of the title compound as a white solid, 72% yield. 1H NMR: consistent with structure. MS (ion spray) 472 (M+).

1. stirringstir
2. customthe reaction at 0° C. under nitrogen for 30 minutes
3. customQuench
4. customthe reaction with 1N HCl
5. concentrationconcentrate
6. extractionextract with 20% isopropanol/chloroform (×2)
7. washWash the combined organic layers with saturated aqueous sodium bicarbonate solution, brine
8. dry with materialdry over magnesium sulfate
9. concentrationconcentrate
10. customPurify by flash chromatography on silica gel (eluting with 0–0.4% methanol/chloroform)