Hydrochloric Acid → HCID 68298700, compound

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl 1-(5-(3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-4-ylamino)pyridin-2-yl)piperidin-3-ylcarbamate (5.7 g, 8.8 mmol) was reacted HCl (100 mL, 1.25M in methanol). The mixture was heated to 40° C. for 16 h. The reaction was diluted with ethyl acetate (100 mL). The resultant solid was filtered and washed with ethyl acetate. The solids were dissolved in a mixture of water, methanol, and acetonitrile. The solution was concentrated by lyophilization to obtain desired product (4.7 g, 81%) as an orange solid: 1H NMR (500 MHz, CD3OD) δ 9.36 (s, 1H), 8.32-8.22 (m, 3H), 8.08 (d, J=9.2 Hz, 1H), 7.90 (dd, J=9.5, 2.6 Hz, 1H), 7.48 (s, 2H), 7.36 (d, J=9.5 Hz, 1H), 4.51-4.45 (m, 1H), 4.11-4.03 (m, 1H), 3.53-3.36 (m, 3H), 2.87-2.78 (m, 1H), 2.27-2.20 (m, 1H), 2.06-1.97 (m, 1H), 1.85-1.72 (m, 2H), 1.25-1.10 (m, 4H); ESI MS m/z 548 [C29H27Cl2N5O2+H]+; HPLC 98.8% (AUC), tR=9.51 min.

Provenance & Evidence