Hydrochloric Acid → HCID 66715542, compound

Participants

Reaction Steps

Following general procedure F, 1-(6-bromo-4-(3-(2-(pyrrolidin-1-yl)ethyl)phenylamino)quinolin-3-yl)ethanone (5.7 g, 13.0 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (4.1 g, 14.2 mmol) to obtain the free base. The purified product was suspended in dichloromethane/methanol (1:1, 100 mL) after which HCl (40 mL, 1.25 M in methanol) was added to form a solution. The solution was concentrated to dryness and the resultant solid was triturated with acetonitrile. The mixture was filtered, washed with acetonitrile, and dried to obtain desired product (5.6 g, 73% over two steps) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ 9.31 (s, 1H), 8.19 (dd, J=8.8, 2.0 Hz, 1H), 7.99 (d, J=8.8 Hz, 1H), 7.75-7.55 (m, 3H), 7.53 (s, 1H), 7.43-7.34 (m, 1H), 7.10 (s, 2H), 3.66 (br s, 2H), 3.48-3.36 (m, 2H), 3.24-3.06 (m, 4H), 2.82 (s, 3H), 2.07 (br s, 4H); APCI MS m/z 520 [C29H27Cl2N3O2+H]+; HPLC>99% (AUC), tR=9.17 min.

Provenance & Evidence