Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178467093, 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 2,6-dichloro-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), 8.47 (d, J=9.0 Hz, 1H), 8.34 (d, J=8.9 Hz, 1H), 8.11 (s, 2H), 5.92 (p, J=4.4 Hz, 1H), 3.21 (d, J=7.2 Hz, 2H), 2.96 (s, 6H), 2.78 (s, 3H), 2.25-2.05 (m, 3H), 1.99-1.88 (m, 2H), 1.62 (dtd, J=14.1, 11.2, 10.8, 3.7 Hz, 3H), 1.20 (s, 1H); ESI MS m/z 487 [M+H]+; HPLC 96.5% (AUC), tR=9.9 min.

Provenance & Evidence