Hydrochloric Acid → 1-(6-(3-Chloro-5-fluoro-4-hydroxyphenyl)-4-((6-(3-(methylamino)pyrrolidin-1-yl)pyridin-3-yl)amino)quinolin-3-yl)ethanone trihydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (1-(5-((3-acetyl-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-4-yl)amino)pyridin-2-yl)pyrrolidin-3-yl)(methyl)carbamate (85 mg, 0.14 mmol) in THF (5 mL) was added water (3 mL) and HCl (6 M in water, 2 mL, 12 mmol). The reaction mixture was heated at 65° C. for 3 h, cooled to room temperature and concentrated. The resultant residue was triturated with dichloromethane to give the desired product (55 mg, 64%) as an orange solid. 1H NMR (500 MHz, MeOD) δ 9.31 (s, 1H), 8.31-8.23 (m, 2H), 8.10-8.03 (m, 2H), 7.95 (dd, J=9.4, 2.4 Hz, 1H), 7.22 (dd, J=11.5, 2.3 Hz, 1H), 7.18-7.11 (m, 2H), 4.14-4.08 (m, 2H), 3.98-3.86 (m, 2H), 3.83-3.74 (m, 1H), 2.84 (s, 3H), 2.79 (s, 3H), 2.71-2.60 (m, 1H), 2.47-2.36 (m, 1H). ESI MS m/z 506 [C27H25ClFN50O2+H]+; HPLC 97.4% (AUC), tR=9.62 min.

Provenance & Evidence