Hydrochloric Acid → HCID 178467086, compound

Participants

Reaction Steps

Following general procedure F, 1-(6-bromo-4-(trans-4-(dimethylamino)cyclohexylamino)quinolin-3-yl)ethanone (4.48 g, 11.0 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (3.65 g, 13.0 mmol) to obtain the free base. The purified product was suspended in dichloromethane/methanol (2:1, 325 mL) after which HCl (115 mL, 1.25 M in methanol) was added to from a solution. The solution was concentrated to ˜100 mL and the resultant solid was filtered, washed with dichloromethane, and dried to obtain desired product (4.2 g, 70% over two steps) as a yellow solid: 1H NMR (500 MHz, MeOD) δ 9.13 (s, 1H), 8.48 (br s, 1H), 8.30 (dd, J=8.8, 1.8 Hz, 1H), 8.01 (d, J=8.7 Hz, 1H), 7.77 (s, 2H), 4.62 (br s, 1H), 3.50-3.46 (m, 1H), 2.91 (s, 6H), 2.75 (s, 3H), 2.58-2.54 (m, 2H), 2.35-2.29 (m, 2H), 1.92-1.82 (m, 4H); ESI MS m/z 472 [C25H27Cl2N3O2+H]+; HPLC>99% (AUC), tR=6.41 min.

Provenance & Evidence