Trifluoroacetic acid → 3-(3-(4-chloro-2-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-ylcarbamoyl)-phenylcarbamoyl)benzylthio)propanoic acid

Participants

Reaction Steps

Into a 50-mL round bottom flask, was placed a solution of tert-butyl 3-(3-(4-chloro-2-(1-(3,4-dimethylphenyl)-1H-pyrazol-3-ylcarbamoyl)phenylcarbamoyl)benzylthio)propanoate (150 mg, 0.24 mmol, 1.00 equiv) in dichloromethane (4 mL), and 2,2,2-trifluoroacetic acid (2 mL). The resulting solution was stirred for 2 h at room temperature. The resulting mixture was concentrated under vacuum. The crude product (100 mg) was purified by reverse phase HPLC eluting with a water/CH3CN gradient containing 0.05% TFA. The product was obtained as 36.3 mg (27%) of a white solid. 1H-NMR (300 MHz, DMSO, ppm): δ 11.82 (s, 1H), 11.48 (s, 1H), 8.52 (d, J=8.70 Hz, 1H), 8.41 (s, 1H), 8.11 (s, 1H), 7.92 (s, 1H), 7.79 (m, 1H), 7.67 (m, 1H), 7.57 (m, 4H), 7.26 (m, 1H), 6.92 (d, J=1.8 Hz, 1H), 3.86 (s, 2H), 2.60 (m, 2H), 2.29 (m, 6H). MS (ES, m/z): 563 [M+H]+.

Provenance & Evidence