PROCESS FOR THE MANUFACTURING OF 3-HYDROXY-N, 16-TRIALKYL-4-OXO-1, 4-DIHYDROPYRIDINE-2-CARBOXAMIDE
Application 666/MUMNP/2004 published 2006-07-07, filed 2004-11-22
The present invention relates to a novel process for the preparation of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I: The method comprises of the TEMPO oxidation of a primary alcohol of 3-O-protected-2-hydroxymethyl-6-alkyl-4H-pyran-4-one of formula III to 3-O-protected-6-alkyl-4-oxo-4H-pyran-2-carboxylic acid of formula II. Reaction of compound of formula II with methylamine and 1,1-carbonyldiimidazole in an inert solvent affords 3-O-protected-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide, which is deprotected to give of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I. Drawing: NIL Total Pages: 27 Fig. Nil
Applicant
APOTEX INC.
150 SIGNET DRIVE, TORONTO, ONTARIO, CANADA M9L 1T9, CANADIAN COMPANY
Inventor
1. TAM TIM FAT 2. LI WANREN
International Info
Classification: C07D 213/81
Publication Number: WO 03/037867
Application Date: 2002-10-30
Priority Information
09/985,269 U.S.A. 2001-11-02