Water → N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-4-(6-methoxypyridin-3-yl)-3-methylbenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(6-fluoro-pyridin-3-yl)-3-methyl-benzenesulfonamide (4.2 g, 16 mmol) and triethylamine (5.1 ml, 36.8 mmol, 2.3 equiv.) in 130 ml acetonitrile was added dropwise at 0° C. phenyl chloroformate (2.4 ml, 19.2 mmol, 1.2 equiv.) After stirring the solution for one hour at room temp., 5-bromo-thiazol-2-ylamine (4.3 g, 24 mmol, 1.5 equiv.) is added in one portion. The mixture was warmed to 60° C., then methanesulfonic acid (1.5 ml, 24 mmol, 1.5 equiv.) was added and the reaction mixture was stirred for one hour at 60° C. After cooling to room temp., the mixture was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium-dihydrate, filtered and evaporated. The crude product was purified on silica-gel with ethyl acetate/n-heptane to give 2.67 g of the title compound as a light brown solid. MS (ES): m/e 470.7 (M−H)

Provenance & Evidence