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

Participants

Reaction Steps

Following general procedure IV-2, (S)-tert-butyl 1-{5-[3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)-1,5-naphthyridin-4-ylamino]pyridin-2-yl}piperidin-3-ylcarbamate (73 mg, 0.11 mmol) was reacted with TFA (3 mL) followed by formation of the trihydrochloride salt to afford the desired product (31 mg, 42%) as an orange solid: 1H NMR (500 MHz, CD3OD) δ 9.52 (br s, 1H), 8.51 (d, J=9.0 Hz, 1H), 8.42 (d, J=9.0 Hz, 1H), 8.23 (d, J=2.6 Hz, 1H), 7.88 (dd, J=9.4, 2.7 Hz, 1H), 7.69 (br s, 2H), 7.24 (d, J=9.5 Hz, 1H), 4.37 (d, J=10.9 Hz, 1H), 4.05-3.95 (m, 1H), 3.50-3.33 (m, 3H), 2.90 (br s, 1H), 2.27-2.17 (m, 1H), 2.06-1.96 (m, 1H), 1.86-1.74 (m, 2H), 1.37-1.18 (m, 4H); ESI MS m/z 549 [M+H]+; HPLC 95.4% (AUC), tR=10.09 min.

Provenance & Evidence