反应详情

温度

90 °C

A mixture of ethyl (4-{4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}phenyl)acetate (552 mg), 4-[(E)-2-(2-ethyl-1,3-thiazol-4-yl)ethenyl]-1-(2-methylphenyl)-1H-pyrazol-3-ol (400 mg), anhydrous potassium carbonate (177 mg) and N,N-dimethylformamide (10 mL) was stirred at 90° C. for 1.5 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with acetone-hexane (1:4-1:3-1:2, v/v). The obtained eluate was subjected to reversed phase HPLC and eluted with acetonitrile-water (10:90-100:0, v/v). The obtained fraction was concentrated, and saturated aqueous sodium hydrogen carbonate was added to the residue. The mixture was extracted with ethyl acetate-tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was washed with ethyl acetate-hexane to give ethyl [4-(4-{[4-({[4-[(E)-2-(2-ethyl-1,3-thiazol-4-yl)ethenyl]-1-(2-methylphenyl)-1H-pyrazol-3-yl]oxy}methyl)-2-methoxyphenoxy]methyl}-5-methyl-1,3-oxazol-2-yl)phenyl]acetate as pale-yellow amorphous form (173 mg, yield 19%).

1. extractionthe mixture was extracted with ethyl acetate
2. washThe ethyl acetate layer was washed with saturated brine
3. dry with materialdried over anhydrous magnesium sulfate
4. concentrationconcentrated
5. washeluted with acetone-hexane (1:4-1:3-1:2
6. washeluted with acetonitrile-water (10:90-100:0
7. concentrationThe obtained fraction was concentrated
8. additionsaturated aqueous sodium hydrogen carbonate was added to the residue
9. extractionThe mixture was extracted with ethyl acetate-tetrahydrofuran
10. washThe organic layer was washed with saturated brine
11. dry with materialdried over anhydrous magnesium sulfate
12. concentrationconcentrated
13. washThe residue was washed with ethyl acetate-hexane