Hydrochloric Acid → HCID 178478722, compound

Participants

Reaction Steps

To a solution of tert-butyl (trans-4-(4-((3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-4-yl)amino)-1H-pyrazol-1-yl)cyclohexyl)carbamate (23 mg, 0.036 mmol) in THF (3 mL) was added trifluoroacetic acid (2 mL). The resultant mixture was heated at 65° C. for 16 h. The mixture was then 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 (2 M in diethyl ether, 2.0 mL, 4 mmol) was added. The resultant solution was concentrated to give the desired product (11.1 mg, 50%) as a yellow solid. 1H NMR (500 MHz, MeOD) δ 9.50 (br s, 1H), 8.22 (d, J=8.7 Hz, 1H), 8.13 (br s, 1H), 8.00 (d, J=8.7 Hz, 2H), 7.63 (s, 2H), 7.36 (br s, 2H), 4.35-4.31 (m, 1H), 3.26-3.17 (m, 1H), 2.97-2.89 (br s, 1H), 2.28-2.16 (m, 4H), 2.04-1.91 (m, 2H), 1.70-1.58 (m, 2H), 1.33-1.20 (m, 4H). ESI MS m/z 536 [C28H27Cl2N5O2+H]+; HPLC 96.0% (AUC), tR=11.44 min.

Provenance & Evidence