Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178467104, compound

Participants

Reaction Steps

Following general procedure II, 1-(6-Chloro-4-{trans-4-[(dimethylamino)methyl]cyclohexylamino}-1,5-naphthyridin-3-yl)ethanone (74 g, 0.21 mmol) was reacted with (6-hydroxypyridin-3-yl)boronic acid (43 g, 0.31 mmol) followed by formation of the dihydrochloride salt to afford the desired product (49 g, 48%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.14 (s, 1H), 8.41-8.29 (m, 4H), 6.76 (d, J=9.5 Hz, 1H), 5.58-5.50 (m, 1H), 3.13 (d, J=6.7 Hz, 2H), 2.94 (s, 6H), 2.75 (s, 3H), 2.49-2.40 (m, 2H), 2.08-2.00 (m, 3H), 1.73-1.61 (m, 2H), 1.39-1.27 (m, 2H); ESI MS m/z 420 [M+H]+; HPLC>99% (AUC), tR=8.43 min.

Provenance & Evidence