3-Fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)aniline → N-(3-fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-1-(4-fluorophenyl)-3-methyl-2-oxopyrrolidine-3-carboxamide

Participants

Reaction Steps

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)-3-methyl-2-oxopyrrolidine-3-carboxylic acid according to the procedure of Example 89. The crude was purified by silica gel flash column chromatography (5% MeOH in CH2Cl2) to afford 26 mg (84%) of the desired product. The crude was purified by silica gel flash column chromatography (5% MeOH in CH2Cl2) to afford 66 mg (62%) of the desired product. LRMS (APCI pos) m/e 616.1 (M+1). 1H-NMR (400 MHz, CD3OD) δ 8.49 (d, 1H), 7.87 (dd, 1H), 7.68 (m, 2H), 7.59 (s, 1H), 7.45 (m, 1H), 7.36 (t, 1H), 7.15 (t, 2H), 6.69 (d, 1H), 4.25 (t, 2H), 3.91 (m, 2H), 3.68 (s, 2H), 2.79 (m, 6H), 2.56 (m, 2H), 2.30 (s, 3H), 2.18 (m, 2H), 1.66 (s, 3H); 19F NMR (376 MHz, CD3OD) δ −119.0, −130.0.

Provenance & Evidence