Trifluoroacetic acid → (S)-(4-{[6-(3-aminopiperidin-1-yl)pyridin-3-yl]amino}-6-(3-chloro-5-fluoro-4-hydroxyphenyl)-1,5-naphthyridin-3-yl)(cyclobutyl)methanone trihydrochloride

Participants

Reaction Steps

Following general procedure IV-2, (S)-tert-butyl[1-(5-{[6-(3-chloro-5-fluoro-4-hydroxyphenyl)-3-(cyclobutanecarbonyl)-1,5-naphthyridin-4-yl]amino}pyridin-2-yl)piperidin-3-yl]carbamate (0.20 mmol) was reacted with TFA (2 mL) followed by formation of the trihydrochloride salt to afford the desired product (94 mg, 72% over two steps) as a orange-brown solid: 1H NMR (500 MHz, CD3OD) δ 9.10 (s, 1H), 8.45 (d, J=9.0 Hz, 1H), 8.36 (d, J=9.0 Hz, 1H), 8.22 (d, J=3.0 Hz, 1H), 7.74 (dd, J=9.3, 3.0 Hz, 1H), 7.63-7.23 (m, 2H), 7.10 (d, J=9.3 Hz, 1H), 4.40 (d, J=10.5 Hz, 1H), 4.38-4.23 (m, 1H), 4.03-3.92 (m, 1H), 3.45-3.36 (m, 2H), 2.60-2.36 (m, 4H), 2.26-2.13 (m, 2H), 2.03-1.90 (m, 2H), 1.81-1.70 (m, 2H); ESI MS m/z 547 [M+H]+; HPLC 98.2% (AUC), tR=10.33 min.

Provenance & Evidence