A Facile Method for the Synthesis of Betrixaban. (September 2015)

• Record Type: Journal Article
• Authors: Li, Jianye; Chen, Ligong; Yan, Xilong; Li, Yang; Wei, Daiyan; Wang, Donghua
• Is Part Of: Journal of chemical research. Volume 39:Number 9(2015)
• Page Start: 524
• Page End: 526
• Publication Date: 2015-09
• Subjects: serine protease -- acylation -- Betrixaban -- N-(5-chloropyridin-2-yl)-2-(4-(N, N-dimethylcarbamimidoyl)benzamido)-5-methoxybenzamide; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.3184/174751915X14400926401559
• Languages: English
• ISSNs: 1747-5198

Abstract

A facile method for the synthesis of N-(5-chloropyridin-2-yl)-2-(4-(N, N-dimethylcarbamimidoyl)benzamido)-5-methoxybenzamide (Betrixaban) from 5-methoxy-2-nitrobenzoic acid is achieved by reduction, acylation, chlorination, acylation and the formation of the amidine. A dechlorinated impurity is avoided in this method. Using tetrahydrofuran as the solvent in the four steps makes its recovery easier. The total yield of the target compound is about 40% and this method is suitable for large-scale production.