Methanesulfonamide → HCID 56602986, compound

Participants

Reaction Steps

A mixture of 4-(4-chloro-2-methoxyphenoxy)-2-fluoro-5-(2-methoxypyridin-3-yl)benzoic acid (Preparation 15, 0.070 g, 0.114 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.112 g, 0.294 mmol) and N,N-diisopropylethylamine (191 μL, 1.09 mmol) in DCM (10 mL) and dimethylformamide (1.1 mL) was stirred at room temperature for 10 minutes, then methyl sulfonamide (0.0397 g, 0.417 mmol) was added. The reaction was heated at 45° C. for 18 hours under a nitrogen atmosphere, then cooled to room temperature and concentrated in vacuo to afford a pale brown residue. This was partitioned between aqueous hydrochloric acid (0.5 M, 10 mL) and DCM (25 mL). The organic extract was washed with aqueous hydrochloric acid (0.5 M, 2×10 mL), dried over sodium sulfate and concentrated in vacuo to afford a pale brown gum (0.062 g). The crude product was purified by preparative A-HPLC to afford the title compound (26.7 mg):

Provenance & Evidence