Method for the preparation of [1,2,4]-triazolo[4,3-a]pyridines

US9643984B2 · kind B2 · utility

Assignee

• AMGEN INC. · US

Inventors

• Matthew Bio · Boston, US
• Eric Fang · Somerville, US
• Jacqueline Milne · Simi Valley, US
• Sean H. WIEDEMANN · Burlington, US
• Ash Wilsily · Somerville, US

Key dates

• Filing date: Jun 24, 2014
• Grant date: May 9, 2017
• Expiry date: Jun 24, 2034

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

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)