Trifluoroacetic acid → (R)-1-(4-((6-(3-aminopiperidin-1-yl)pyridin-3-yl)amino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)-1,5-naphthyridin-3-yl)-2-methylpropan-1-one trihydrochloride

Participants

Reaction Steps

Following general procedure IV-2, (R)-tert-butyl (1-(5-((6-(3-chloro-5-fluoro-4-hydroxyphenyl)-3-isobutyryl-1,5-naphthyridin-4-yl)amino)pyridin-2-yl)piperidin-3-yl)carbamate (168 mg, 0.26 mmol) was reacted with TFA (2 mL) followed by formation of the trihydrochloride salt to afford the desired product (110 mg, 78%) as an orange solid: 1H NMR (500 MHz, CD3OD) δ 9.31 (s, 1H), 8.35 (s, 2H), 8.18 (d, J=2.5 Hz, 1H), 7.64 (d, J=9.0, 2.5 Hz, 1H), 7.38 (bs, 1H), 7.22-7.12 (m, 1H), 7.02 (d, J=9.0 Hz, 1H), 4.44-4.32 (m, 1H), 3.98-3.90 (m, 1H), 3.82-3.70 (m, 1H), 3.46-3.22 (m, 3H), 2.22-2.12 (m, 1H), 2.01-1.88 (m, 1H), 1.80-1.68 (m, 2H), 1.36-1.20 (m, 6H); ESI MS m/z 535 [M+H]+; HPLC>99% (AUC), tR=10.07 min.

Provenance & Evidence