Triethylamine → HCID 52913370, compound

Participants

Reaction Conditions

Reaction Steps

2,2,2-trifluoroethanesulfonyl chloride (0.83 mL, 7.7 mmol, 1.5 equiv) was added to a solution of 2-(3-{1-ethyl-5-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)propan-2-amine (2.0 g, 5.1 mmol, 1 equiv) and triethylamine (1.1 mL, 7.7 mmol, 1.5 equiv) in dichloromethane (51 mL) at −78° C. The reaction mixture was stirred at −78° C. for 10 minutes, and then the cooling bath was removed. After stirring for 20 minutes, the reaction mixture was partitioned between dichloromethane and citric acid solution (1 M). The organic layer was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash-column chromatography on silica gel (hexanes, grading to 50% ethyl acetate-hexanes) to afford N-[1-(3-{1-ethyl-5-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)-1-methylethyl]-2,2,2-trifluoroethanesulfonamide (2.04 g, 74%) as a white solid. Calcd (M+1)+: 536.1. Found: 536.1. 1H NMR (600 MHz, cdcl3) δ 7.92 (s, 1H), 7.70 (d, J=7.3, 1H), 7.65 (d, J=8.7, 2H), 7.48-7.39 (m, 2H), 7.22 (d, J=8.6, 2H), 6.06 (s, 1H), 5.01 (s, 1H), 4.11 (q, J=7.3, 2H), 3.42 (q, J=8.9, 2H), 1.83 (s, 6H), 1.45 (t, J=7.3, 3H).

Provenance & Evidence