Benzoyl Peroxide → (E)-N-(5-bromo-thiazol-2-yl)-3-cyclohexyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-acrylamide

温度

90 °C

A suspension of (E)-3-cyclohexyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-N-thiazol-2-yl-acrylamide (prepared in Example 12, 150 mg, 3.27 mmol) and N-bromosuccinimide (69 mg, 0.384 mmol) in carbon tetrachloride (2 mL) at 25° C. was treated with benzoyl peroxide (4.65 mg, 0.02 mmol). The resulting reaction mixture was heated to 90° C. where it was stirred overnight at this temperature. The reaction mixture was then allowed to cool to 25° C. and then concentrated in vacuo. The residue was dissolved in ethyl acetate (25 mL). The organic phase was then washed with water (1×30 mL) and a saturated aqueous sodium chloride solution (1×30 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 4/1 hexanes/ethyl acetate) afforded (E)-N-(5-bromo-thiazol-2-yl)-3-cyclohexyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-acrylamide (59 mg, 33%) as an amorphous white solid.

1. customThe resulting reaction mixture
2. temperatureto cool to 25° C.
3. concentrationconcentrated in vacuo
4. dissolutionThe residue was dissolved in ethyl acetate (25 mL)
5. washThe organic phase was then washed with water (1×30 mL)
6. dry with materiala saturated aqueous sodium chloride solution (1×30 mL), dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORDレコード

ord-95ce4fbb35a447418124f4ebc1c2acca

出典データセット

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06353111B1