Hydrochloric Acid → 1-(4-(6-(3-Aminopiperidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)ethanone

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Reaction Steps

tert-butyl 1-(5-(3-acetyl-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-4-ylamino)pyridin-2-yl)piperidin-3-ylcarbamate (80 mg, 0.132 mmol) was dissolved in dichloromethane (5 mL). To this solution was added a 2.0 M HCl solution in diethyl ether (2 mL) the mixture was stirred for 16 h at room temperature where a precipitate formed. The precipitate was filtered off, washed with dichloromethane (10 mL), dried under vacuum to obtain the desired product as the HCl salt (30 mg, 45%) as a yellow-orange solid: 1H NMR (500 MHz, MeOD) δ 9.26 (s, 1H), 8.24 (d, J=2.9 Hz, 1H), 8.20 (dd, J=8.9, 1.9 Hz, 1H), 7.99 (d, J=8.9 Hz, 1H), 7.95 (d, J=2.0 Hz, 1H), 7.68 (dd, J=9.1, 2.8 Hz, 1H), 7.11 (d, J=9.1 Hz, 1H), 7.04 (m, 2H), 4.54 (s, 1H), 4.02 (d, J=12.7 Hz, 1H), 2.80 (s, 3H), 2.18 (m, 1H), 1.94 (m, 1H), 1.74 (m, 2H); ESI MS m/z 506, [C27H25ClFN5O2+H]+; HPLC 95.2% (AUC), tR=10.84 min.

Provenance & Evidence