Tetrafluoro-m-phenylenediamine dihydrochloride → 1-[6-(3-Chloro-5-fluoro-4-hydroxyphenyl)-4-{4-[(4-methylpiperazin-1-yl)methyl]phenylamino}-1,5-naphthyridin-3-yl]ethanone trihydrochloride

Participants

Reaction Steps

Following general procedure II, 1-(6-chloro-4-{4-[(4-methylpiperazin-1-yl)methyl]phenyl amino}-1,5-naphthyridin-3-yl)ethanone (74 mg, 0.18 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (74 mg, 0.27 mmol) followed by formation of the dihydrochloride salt to afford the desired product (96 mg, 93%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.32 (s, 1H), 8.44 (d, J=9.1 Hz, 1H), 8.34 (d, J=9.1 Hz, 1H), 7.65 (d, J=7.6 Hz, 2H), 7.48 (d, J=8.0 Hz, 2H), 7.31 (br s, 1H), 7.12 (br s, 1H), 4.26 (br s, 2H), 3.45 (br s, 8H), 2.97 (s, 3H), 2.80 (s, 3H); ESI MS m/z 520 [M+H]+; HPLC>99% (AUC), tR=9.37 min.

Provenance & Evidence