4-Methylmorpholine → HCID 57436518, compound

Participants

Reaction Steps

To a solution of 4-iodobenzoic acid (181 mg, 0.7 mmol) in methylene chloride (2 mL), diethyl cyanophosphonate (115 μL, 0.8 mmol) and 4-methylmorpholine (160 μL, 1.5 mmol) were added at room temperature and allowed to stir for 15 min. A solution of 3-(3-aminopropylamino)-N-tert-butylbenzo[d]isothiazole-6-sulfonamide (238 mg, 0.7 mmol) in methylene chloride (4 mL) was then added and the resulting reaction mixture was allowed to stir overnight. The reaction mixture with diluted with methylene chloride (20 mL), washed with 10% HCl aqueous solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography, on silica gel, eluting with 1:1 ethyl acetate:hexanes provided N-(3-(6-(N-tert-butylsulfamoyl)benzo[d]isothiazol-3-ylamino)propyl)-4-iodobenzamide (252 mg). 1H NMR (300 MZh, CDCl3): 8.47 (d, 1H), 7.96 (dd, 1H), 7.86 (d, 1H), 7.82 (d, 2H), 7.60 (d, 2H), 7.37 (t, 1H), 6.19 (br s, 1H), 4.98 (s, 1H), 3.75 (t, 2H), 3.60 (dd, 2H), 2.02 (q, 2H), 1.29 ppm (s, 9H). 13C NMR (CDCl3): 167.25, 159.79, 154.96, 139.87, 138.01, 134.16, 128.91, 126.28, 121.54, 121.19, 98.76, 55.46, 43.08, 40.33, 37.32, 30.66, 30.06. MW=572 confirmed by LC-MS, tr=14.28 min (Method Y) MH+=573.

Provenance & Evidence