Process for preparing a dipeptidyl peptidase IV inhibitor and intermediates employed therein

US7186846B2 · kind B2 · utility

Assignee

• Bristol-Myers Squibb Company · US

Inventors

• Padam N. Sharma · Gurnee, US
• Edward J. Gublo · Liverpool, US
• Gabriel Galvin · Manlius, US
• Susan D. Boettger · Fayetteville, US
• Saibaba Racha · Smithtown, US

Key dates

• Filing date: Mar 28, 2005
• Grant date: Mar 6, 2007
• Expiry date: Jul 6, 2025

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2603/74
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process is provided for preparing a dipeptidyl peptidase IV inhibitor of the structurewhereinis treated with TFAA in isopropyl acetate to protect the tertiary hydroxyl group as a trifluoroacetate group to form 4(which is a novel intermediate)which is converted to acid chloride compound 5(which is a novel compound)using Vilsmeier reagent or other chloro reagent and coupled with compound 6 in a heterogeneous mixture of ethyl acetate and aqueous bicarbonate to give compound 7The N,O-bis(trifluoroacetyl) groups of compound 7 are deprotected to give free base compound 10.