Triethylamine → N-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxopyrrolidine-3-carboxamide

Participants

Reaction Steps

A solution of 1-(4-fluorophenyl)-2-oxopyrrolidine-3-carboxylic acid (38 mg, 0.169 mmol), EDCI (88 mg, 0.461 mmol), and HOBt (62 mg, 0.461 mmol) in DMF (3 ml) was stirred at room temperature for 1 hour. 3-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)aniline (Example 1, Step B; 40 mg, 0.154 mmol) was added followed by Et3N (0.064 mL, 0.461 mmol). After stirring for 2 hours, the reaction mixture was diluted with EtOAc and washed with saturated aqueous NH4Cl, saturated aqueous NaHCO3, and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (3:1=Et2O:EtOAc to 1:3=Et2O:EtOAc) to afford 38 mg (53%) of the desired product. 1H NMR (400 MHz, CD3OD/CDCl3) δ 8.45 (d, 1H), 7.92 (d, 1H), 7.85 (dd, 1H), 7.61 (m, 2H), 7.54 (d, 1H), 7.44 (m, 1H), 7.30 (t, 1H), 7.12 (m, 2H), 6.59 (d, 1H), 3.99 (m, 2H), 3.80 (dd, 1H), 2.67 (m, 1H), 2.52 (m, 1H); 19F NMR (376 MHz, CD3OD/CDCl3) δ −117.6, −128.3. LRMS (ESI pos) m/e 466.1 (M+1).

Provenance & Evidence