1-Benzyl-5-chloro-2-oxo-1,2-dihydro-3-pyridinecarboxylic acid → 1-benzyl-5-chloro-N-(3-fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-oxo-1,2-dihydropyridine-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-benzyl-5-chloro 2-oxo-1,2-dihydropyridine-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 16.7 mg (52%) of the desired product. LRMS (APCI pos) m/e 642.1, 644.1 (M+1, Cl pattern). 1H-NMR (400 MHz, CD3OD) δ 8.50 (t, 2H), 8.29 (d, 1H), 8.02 (dd, 1H), 7.59 (s, 1H), 7.33-7.48 (m, 7H), 6.71 (d, 1H), 5.32 (s, 2H), 3.67 (s, 2H), 2.56-2.74 (m, 8H), 2.30 (s, 3H); 19F NMR (376 MHz, CD3OD) δ −129.7.

Provenance & Evidence