(S)-tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamate → (S)-tert-Butyl 1-[5-(3-acetyl-6-chloro-1,5-naphthyridin-4-ylamino)pyridin-2-yl]piperidin-3-ylcarbamate

Participants

Reaction Steps

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone (260 mg, 1.1 mmol) was reacted with (S)-tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamate (470 mg, 1.6 mmol) to afford the desired product (350 mg, 65%) as an orange-red solid: 1H NMR (300 MHz, CDCl3) δ 11.48 (s, 1H), 9.04 (s, 1H), 8.10 (d, J=8.7 Hz, 1H), 8.01 (d, J=2.8 Hz, 1H), 7.46 (d, J=8.7 Hz, 1H), 7.31 (dd, J=9.0, 2.8 Hz, 1H), 6.73 (d, J=9.0 Hz, 1H), 4.80 (br s, 1H), 3.85-3.62 (m, 3H), 3.55-3.25 (m, 3H), 2.71 (s, 3H), 1.96-1.84 (m, 1H), 1.82-1.70 (m, 1H), 1.72-1.55 (m, 1H), 1.45 (s, 9H); ESI MS m/z 497 [M+H]+

Provenance & Evidence