Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178467116, compound

Participants

Reaction Steps

Following general procedure II, 1-(6-chloro-4-{cis-4-[(dimethylamino)methyl]-cyclohexyl amino}-1,5-naphthyridin-3-yl)ethanone (120 mg, 0.30 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (100 mg, 0.30 mmol) followed by formation of the dihydrochloride salt to afford the desired product (150 mg, 81%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 9.17 (s, 1H), 8.46 (d, J=9.0 Hz, 1H), 8.45-8.30 (m, 1H), 7.99 (q, J=2.7, 1.7 Hz, 1H), 7.90-7.82 (m, 1H), 5.93 (p, J=4.2 Hz, 1H), 3.20 (d, J=7.1 Hz, 2H), 2.95 (s, 6H), 2.78 (s, 3H), 2.15 (dddt, J=44.4, 14.7, 11.4, 4.1 Hz, 3H), 2.01-1.86 (m, 2H), 1.61 (dtd, J=14.3, 10.8, 3.6 Hz, 3H), 1.20 (s, 1H); ESI MS m/z 471 [M+H]+; HPLC 95.7% (AUC), tR=9.9 min.

Provenance & Evidence