公开(公告)号：US09643984B2

公开(公告)日：2017-05-09

申请号：US14900976

申请日：2014-06-24

Applicant: AMGEN, INC.

Inventor： Matthew Bio ,  Eric Fang ,  Jacqueline E. Milne ,  Sean Wiedemann ,  Ash Wilsily

IPC: C07D471/04 ,  C07D519/00

CPC classification number: C07D519/00 ,  C07D471/04

Abstract: Disclosed herein are methods for preparing [1,2,4]triazolo[4,3-a]pyridines, particularly (R)-6-(1-(8-fluoro-6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)-3-(2-methoxyethoxy)-1,6-naphthyridin-5(6H)-one, and precursors thereof, such as a method comprising reacting (R)—N-(3-fluoro-5-(1methyl-1H-pyrazol-4-yl) pyridin-2-yl)-2-(3-(2-methoxyethoxy)-5-oxo-1,6-naphthyridin-6(5H)yl) propanehydrazide (“HYDZ”): (HYDZ) under conditions sufficient to form (R)-6-(1-(8-fluoro-6-(1-methyl-IH-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)-3-(2-methoxyethoxy)-1,6-naphthyridin-5(6H)-one (“A”): (A)