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

Temperature

90 °C

A suspension of (E)-3-cycloheptyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-N-thiazol-2-yl-acrylamide (prepared in Example 17, 63 mg, 0.133 mmol) and N-bromosuccinimide (26 mg, 0.146 mmol) in carbon tetrachloride (2 mL) at 25° C. was treated with benzoyl peroxide (2 mg, 0.006 mmol). The resulting reaction mixture was heated to 90° C. where it was stirred overnight at this temperature. The reaction mixture was 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, 5/1 hexanes/ethyl acetate) afforded the (E)-N-(5-bromo-thiazol-2-yl)-3-cycloheptyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-acrylamide (35.5 mg, 48%) 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 record

ord-6a4ebe65fed94d2682e088c3218a80dc

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06353111B1