Hydrochloric Acid → HCID 178467107, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-((trans-4-((3-acetyl-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-4-yl)amino)cyclohexyl)methyl)piperazine-1-carboxylate (66 mg, 0.10 mmol) in THF (5 mL) was added water (5 mL) and aqueous 6 N HCl (1.0 mL). The reaction mixture was heated at 65° C. for 2 h, cooled to room temperature and concentrated. The resultant residue was purified by preparative HPLC (C18 silica, 10-90% acetonitrile/water with 0.05% TFA). The residue was dissolved in methanol (5 mL) and HCl (6 M in water, 0.5 mL, 3 mmol) was added. The resultant solution was concentrated to give the desired product (24.2 mg, 41%) as an off-white solid. 1H NMR (500 MHz, MeOD) δ 9.10 (s, 1H), 8.48 (s, 1H), 8.27 (dd, J=8.7, 1.7 Hz, 1H), 7.98 (d, J=8.7 Hz, 1H), 7.59 (s, 1H), 7.52 (d, J=11.3 Hz, 1H), 4.57-4.53 (br s, 1H), 3.67 (br s, 4H), 3.50 (br s, 2H), 3.17 (br s, 2H), 2.74 (s, 3H), 2.46 (d, J=11.9 Hz, 2H), 2.18 (d, J=12.5 Hz, 2H), 2.10 (br s, 1H), 1.83-1.77 (m, 2H), 1.41-1.34 (m, 2H). ESI MS m/z 511 [C28H32ClFN4O2+H]+; HPLC 98.3% (AUC), tR=9.38 min.

Provenance & Evidence