Methanesulfonamide → 3-chloro-4-(4-chloro-3-(trifluoromethyl)phenoxy)-2-fluoro-N-(methylsulfonyl)benzamide

Participants

Reaction Steps

3-chloro-4-(4-chloro-3-(trifluoromethyl)phenoxy)-2-fluorobenzoic acid (Preparation 153, 0.133 g, 0.360 mmol) was slurried in dichloromethane (0.6 mL). N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (100 mg, 0.54 mmol), 1-hydroxybenzotriazole (49 mg, 0.36 mmol) and N,N-diisopropylethylamine (75 μL, 0.43 mmol) were added to the slurry. The reaction mixture was stirred 20 minutes then methanesulfonamide (100 mg, 1.1 mmol) was added and the stirring continued for 18 hours at ambient temperature. The solvent was removed in vacuo to leave a residue. The residue was purified by semi-preparative reverse phase HPLC (Phenomenex 100×21.2 mm 10 micron C18 column. 20 mL/minutes. Gradient 85% A to 100% B over 25 minutes. Solvent A: 7800 water/200 acetonitrile/8 trifluoroacetic acid. Solvent B: 7200 acetonitrile/800 water/8 trifluoroacetic acid, 254 nM UV detection) to afford the title compound as a white solid (132 mg).

Provenance & Evidence