4-Fluoroaniline → 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-oxo-1,2-dihydropyridine-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-oxo-1,2-dihydropyridine-3-carboxylic acid (prepared from methyl 2-oxo-2H-pyran-3-carboxylate with 4-fluoroaniline and followed by hydrolysis using the methods described in US 2005/0239820) according to the procedure for Example 89. The crude was purified by silica gel flash column chromatography (5% MeOH in CH2Cl2) to afford 3 mg (19%) of the desired product. 1H NMR (400 MHz, CD3OD/CDCl3) δ 8.73 (dd, 1H), 8.45 (d, 1H), 7.98 (dd, 1H), 7.84 (dd, 1H), 7.58 (s, 1H), 7.48 (m, 2H), 7.40 (d, 1H), 7.31 (t, 2H), 6.74 (t, 1H), 6.63 (d, 1H), 3.64 (s, 2H), 2.60-2.76 (m, 8H), 2.33 (s, 3H); 19F NMR (376 MHz, CD3OD/CDCl3) δ −112.1, −127.6. LRMS (ESI pos) m/e 612.1 (M+1).

Provenance & Evidence