1-(4-Fluorophenyl)-2-oxo-3-pyrrolidinecarboxylic acid → N-(3-fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxopyrrolidine-3-carboxamide

Participants

Reaction Steps

The title compound was prepared from 3-fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)aniline (Example 17, Step B) and 1-(4-fluorophenyl)-2-oxopyrrolidine-3-carboxylic acid according to the procedure described for Example 89. The crude was purified by silica gel flash column chromatography (5% MeOH in CH2Cl2) to afford 4.7 mg (31%) of the desired product. 1H NMR (400 MHz, CD3OD) δ 8.49 (d, 1H), 7.89 (dd, 1H), 7.63 (m, 2H), 7.60 (s, 1H), 7.45 (m, 1H), 7.37 (t, 1H), 7.14 (t, 2H), 6.69 (d, 1H), 3.97 (m, 2H), 3.68 (s, 2H), 2.75 (m, 4H), 2.58 (m, 3H), 2.47 (m, 3H), 2.30 (s, 3H); 19F NMR (376 MHz, CD3OD) δ −119.2, −129.9. LRMS (ESI pos) m/e 602.3 (M+1).

Provenance & Evidence