Isopropyl isocyanate → 3-Chloro-4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-N-(isopropylcarbamoyl)benzenesulfonamide

Participants

Reaction Steps

To a stirred solution of aluminum trichloride (75 mg, 513 μmol, 3.0 eq) in toluene (1 mL, anhyd) was added isopropylisocyanate (17 μL, 170 μmol, 1.0 eq). After 3 min of stirring at room temperature, 3-chloro-4-((5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)benzenesulfonamide (100 mg, 170 μmol, 1.0 eq) was added neat. The reaction mixture was heated at 80° C. for 16 h, then partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (3×), washed with water, brine, then dried and concentrated. Purification (silica gel chromatography, 20% methanol/ethyl acetate) provided the title compound (50 mg) as an off-white foam. 1H NMR (DMSO-d6, 400 MHz): δ 8.33 (s, 1H), 7.78 (s, 1H), 7.63 (d, J=7.8 Hz, 1H), 7.43 (d, J=8.2 Hz, 1H), 7.31 (d, J=8.2 Hz, 1H), 7.22 (s, 1H), 6.98-6.87 (m, 4H), 6.41-6.35 (m, 2H), 6.05 (br s, 1H), 4.22 (s, 2H), 3.61-3.50 (m, 1H), 1.44 (s, 6H), 0.97 (d, J=6.6 Hz, 6H); MS (EI) m/z 671 (MH)+.

Provenance & Evidence