Synthesis of Repaglinide Congeners

T. S. S. Sundaram, Dhanraj; Mitra, Jayati; Rajesh, C.; Islam, Aminul; Prabahar, Koilpillai Joseph; Venkateswara Rao, Battula; Paul Douglas, Sanasi

doi:10.6084/m9.figshare.1463383.v3

lsyc_a_1064139_sm7302.pdf (32.07 MB)

Synthesis of Repaglinide Congeners

Version 3 2015-10-08, 12:43

Version 2 2015-10-08, 12:43

Version 1 2015-09-17, 00:00

journal contribution

posted on 2015-10-08, 12:43 authored by Dhanraj T. S. S. Sundaram, Jayati Mitra, C. Rajesh, Aminul Islam, Koilpillai Joseph Prabahar, Battula Venkateswara Rao, Sanasi Paul Douglas

This report describes a synthesis of two potent impurities of repaglinide, benzyl repaglinide 1 and repaglinide isomer 2, from commercially available raw materials: 2-fluoro benzonitrile, (S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butylamine (5), and 3-ethoxy-[4-(ethoxycarbonyl)phenyl]acetic acid (7). These impurities are the crucial components in determining the quality of the drug substance, repaglinide, during its manufacturing.