反应详情

A mixture of {3-[4-({4-[({4-[(E)-2-(2-ethyl-1,3-thiazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]phenyl}amine (100 mg), methanesulfonyl chloride (0.013 mL), triethylamine (0.024 mL) and tetrahydrofuran (1 mL) was stirred at room temperature for 1 hr. The reaction mixture was added to saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate-tetrahydrofuran. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The 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 to give N-{3-[4-({4-[({4-[(E)-2-(2-ethyl-1,3-thiazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]phenyl}methanesulfonamide (37 mg, yield 33%). Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 113-115° C.

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