Potassium Carbonate → 4-((3-((4-(piperidin-1-yl)-2-((1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)carbamoyl)phenyl)carbamoyl)benzyl)thio)benzoic acid

Participants

Reaction Steps

Into a round bottom flask was placed a solution of intermediate 21a (0.0580 mmol, 1 equiv), 4-mercaptobenzoic acid (11 mg, 0.0696 mmol, 1.2 equiv), potassium carbonate (24 mg, 3 equiv), and DMF (1 mL). The solution was stirred at room temperature overnight. The solvent was evaporated at reduced pressure and the residue was partitioned between dichloromethane and water. The organic phase was dried (Na2SO4). The solvent was evaporated and the residue was purified by reverse phase HPLC eluting with 0.05% TFA in a water/acetonitrile gradient to give 34 mg of product. 1H-NMR (400 MHz, DMSO, ppm): δ 11.55(s, 1H), 11.48(s, 1H), 8.67(d, J=2.6 Hz, 1H), 8.32(d, J=8.3 Hz, 1H), 8.19(S, 1H), 8.16(d, J=7.8 Hz, 1H), 8.01(s, 1H), 7.85-7.71(m, 5H), 7.65(d, J=7.5 Hz, 3H), 7.52(t, J=7.7 Hz, 1H), 7.44(d, J=8.7 Hz, 2H), 7.04(d, J=2.7 Hz, 1H), 4.46(s, 2H), 3.30(s, 4H), 1.70(s, 4H), 1.59(s, 2H). MS (ES, m/z) 700 [M+H]+.

Provenance & Evidence