Trifluoroacetic acid → (S)-1-(4-{[6-(3-Aminopiperidin-1-yl)pyridin-3-yl]amino}-6-(3,5-dichloro-4-hydroxyphenyl)-1,5-naphthyridin-3-yl)ethanone trihydrochloride

Participants

Reaction Steps

Following general procedure IV-2, (S)-tert-butyl [1-(5-{[3-acetyl-6-(3,5-dichloro-4-hydroxy-phenyl)-1,5-naphthyridin-4-yl]amino}pyridin-2-yl)piperidin-3-yl]carbamate (0.197 mmol) was reacted with TFA (2 mL) followed by formation of the trihydrochloride salt to afford the desired product (42 mg, 33% over two steps) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.39 (s, 1H), 8.49 (d, J=9.0 Hz, 1H), 8.41 (d, J=9.0 Hz, 1H), 8.25 (d, J=2.6 Hz, 1H), 7.92 (dd, J=9.5, 2.6 Hz, 1H), 7.57 (s, 2H), 7.27 (d, J=9.5 Hz, 1H), 4.37 (d, J=10.9 Hz, 1H), 4.02-3.99 (m, 1H), 3.52-3.32 (m, 3H), 2.84 (s, 3H), 2.24-2.22 (m, 1H), 2.07-1.95 (m, 1H), 1.82-1.77 (m, 2H); ESI MS m/z 523 [M+H]+; HPLC 97.5% (AUC), tR=9.56 min.

Provenance & Evidence