Methanesulfonamide → HCID 52933067, compound

Participants

Reaction Steps

1,1-Carbonyldiimidazole (671 mg, 4.14 mmol) was added to a stirred solution of {[3-(2′,4′,5′-trifluoro-biphenyl-4-yloxymethyl)-benzoyl]-methyl-amino}-acetic acid (1.1 g, 3.07 mmol) in 5 mL NMP in an ice bath under argon for 3 hrs. To this mixture was added methanesulfonamide (437 mg, 4.6 mmol) and 1,8-diazobicyclo[5.4.0]undec-7-ene (0.684 mL, 4.6 mmol). The reaction was stirred at RT overnight. An additional 0.5 equiv. each of 1,1-carbonyldiimidazole (335 mg, 2.07 mmol), methanesulfonamide (197 mg, 2.07 mmol) and 1,8-diazobicyclo[5.4.0]undec-7-ene (0.34 mL, 2.07 mmol) were added and let stir over the weekend. The reaction mixture was concentrated, dissolved in 250 mL ethyl acetate, washed with H2O and concentrated. The crude product was purified by flash chromatography with a 0-25% gradient of ethyl acetate/MeOH/AcOH (95:5:1) in CH2Cl2 and lyophilized to yield 153 mg (38.6%) of N-(2-methanesulfonylamino-2-oxo-ethyl)-N-methyl-3-(2′,4′,5′-trifluoro-biphenyl-4-yloxymethyl)-benzamide as an amorphous solid. LC-MS (ES) calculated for C24H21F2NO5S, 506.50; found m/z 507 [M+H]+.

Provenance & Evidence