Tetrafluoro-m-phenylenediamine dihydrochloride → 1-(6-(3,5-Dichloro-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)-phenylamino)-1,5-naphthyridin-3-yl)ethanone (74 mg, 0.18 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (78 mg, 0.27 mmol) followed by formation of the dihydrochloride salt to afford the desired product (84 mg, 77%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.33 (s, 1H), 8.45 (d, J=9.1 Hz, 1H), 8.36 (d, J=9.0 Hz, 1H), 7.70 (d, J=8.1 Hz, 2H), 7.49 (d, J=8.1 Hz, 2H), 7.38 (br s, 2H), 4.45 (s, 2H), 3.55 (br s, 8H), 2.99 (s, 3H), 2.81 (s, 3H); ESI MS m/z 536 [M+H]+; HPLC>99% (AUC), tR=9.57 min.

Provenance & Evidence