Potassium Carbonate → HCID 19024436, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 171 mg (0.391 mmole) of N-butyl-N-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]carbamoyl chloride (from Step F), 63.9 mg (0.394 mmole) of α,α,α-trifluoro-o-cresol, 66 mg (0.48 mmole) of anhydrous potassium carbonate, and 3 mL of DMF was stirred under N2 at 90° C. overnight. The cooled mixture was partitioned between 20 mL of 2N HCl and 20 mL of EtOAc. The organic layer was washed with H2O (2×30 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The residual oil was flash chromatographed on silica gel (gradient elution with 20-35% EtOAc in hexane to yield 37.4 mg (17%) of the title compound as a yellow oil, homogeneous by TLC in 3:1 hexane-EtOAc; FAB-MS m/e 562 (M+1)+. The 1H NMR spectrum indicated the presence of two rotameric forms.

Provenance & Evidence