Triethylamine → HCID 11296120, compound

Participants

Reaction Steps

4-(Chlorosulfonyl)benzoic acid (0.11 g, 0.5 mmol) in 5 mL of THF was added dropwise to a stirred solution of [4-(3-aminophenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (0.098 g, 0.25 mmol) and triethylamine (0.4 mL, 0.29 mmol) in 5 mL of THF at room temperature. The reaction mixture was stirred overnight, diluted with ethyl acetate, washed with water, and concentrated. The residue was purified by semi-preparative HPLC (Column: Phenomenex C18 Luna 21.6 mm×60 mm, 50M; Solvent A: Water (0.1% TFA buffer); Solvent B: Acetonitrile (0.1% TFA buffer); Solvent Gradient: Time 0: 0% B; 10 min: 100% B; Hold 100% B 5 min. Flow Rate: 22.5 mL/min). The product was collected based on UV absorption and concentrated to give the title compound as a brown solid (0.075 g, 50%): MS (EI) m/z 601.1 (M+H)+; 1H NMR (DMSO-d6): δ 7.03 (d, J=7.7 Hz, 1H), 7.33 (t, J=8.0 Hz, 1H), 7.39 (t, J=7.8 Hz, 2H), 7.56 (t, J=7.4 Hz, 1H), 7.60-8.75 (m, 9H), 8.06 (d, J=8.6 Hz, 1H), 8.36 (d, J=7.3 Hz, 1H), 9.16 (s, 1H), 10.34 (s, 1H).

Provenance & Evidence