反应详情

To MeOH (4 mL) at rt was added a 25% (w/w) solution of NaOMe in MeOH followed by addition of N-cyclopropyl-3-(2-mercaptoacetamido)-4-methylbenzamide a (200 mg, 10.8 mmol). After stirring at rt for 15 min, 200 mg (10.6 mmol) of 2-(4-chlorophenyl)-2-cyanovinyl benzenesulfonate (prepared as described in J. Med. Chem., 6(47):1448 (2004)) was added and the resulting solution was warmed to 60° C. for 2 h then allowed to cool to rt and stir for an additional 15 h. The mixture was concentrated under vacuum to remove the MeOH then water (20 mL) was added and the solution was extracted with EtOAc (200 mL). The organic extract was washed with water, brine, then dried over anhyd Na2SO4, filtered, and concentrated under vacuum to afford 300 mg of an orange solid as the crude product. This material was purified by reverse-phase preparative HPLC to afford 50 mg of a light yellow solid as the title compound (Example 209). HPLC Ret time=3.57 min. LCMS [M+H]+ 426.17.

1. temperaturethe resulting solution was warmed to 60° C. for 2 h
2. temperatureto cool to rt
3. stirringstir for an additional 15 h
4. concentrationThe mixture was concentrated under vacuum
5. customto remove the MeOH
6. additionwater (20 mL) was added
7. extractionthe solution was extracted with EtOAc (200 mL)
8. extractionThe organic extract
9. washwas washed with water, brine
10. dry with materialdried over anhyd Na2SO4
11. filtrationfiltered
12. concentrationconcentrated under vacuum