1,2-Dichloroethane → HCID 57948492, compound

Participants

Reaction Steps

To a solution of 0.04 g (0.18 mmol) [4-(3-thienyl)phenyl]acetic acid in 0.75 mL DMF was added 0.06 g (0.2 mmol) 2,2,2-trifluoro-1-(5-methoxypyridin-2-yl)ethanamine hydrochloride, 0-1 mL (0.6 mmol) triethylamine, 0.03 g (0.2 mmol) HOAt, and 0.05 g (0.2 mmol) EDC and the mixture stirred for 1 hour at room temperature. Purification (no workup) by preparative reverse phase HPLC (linear gradient 5 to 95% CH3CN/H2O over 30 min, 0.05% added TFA, C18 SunFire 19×150 mm) afforded 2-[4-(3-thienyl)phenyl]-N-[(1S)-2,2,2-trifluoro-1-(5-methoxypyridin-2-yl)ethyl]acetamide high resolution mass spec calc for C20H17F3N2O2S 407.1036, found 407.1043. 1H NMR (400 MHz, CDCl3) δ 8.20 (d, 1H, J=2.84 Hz); 7.58 (d, 2H, J=8.33 Hz); 7.46 (t, 1H, J=2.10); 7.39 (d, 2H, J=2.10 Hz); 7.30 (m, 3H); 7.22 (dd, 1H, J=2.93 and 8.60 Hz); 5.73 (dq, 1H, J=7.14 and 7.14 Hz); 3.86 (s, 3); 3.70 (s, 2H)

Provenance & Evidence