US 11,731,963 B2
Process for preparing 5-[[4-[2-[5-(1-hydroxyethyl)-2-pyridinyl]ethoxy]phenyl]-methyl]-2,4-thiazolidinedione and salts thereof
Ana Maria García Collazo, Barcelona (ES); Wolter Ten Hoeve, Groningen (NL); Johannes Nicolaas Koek, Groningen (NL); Johannes B. M. Rewinkel, Oss (NL); and Sander De Wilde, Oss (NL)
Assigned to Minoryx Therapeutics S.L., Barcelona (ES)
Filed by Minoryx Therapeutics S.L., Barcelona (ES)
Filed on Sep. 20, 2021, as Appl. No. 17/479,838.
Application 17/479,838 is a continuation of application No. 16/470,866, granted, now 11,124,505, previously published as PCT/IB2017/058374, filed on Dec. 22, 2017.
Claims priority of application No. 16382648 (EP), filed on Dec. 23, 2016.
Prior Publication US 2022/0204496 A1, Jun. 30, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 417/12 (2006.01); C07D 213/127 (2006.01); C07F 7/10 (2006.01)
CPC C07D 417/12 (2013.01) [C07D 213/127 (2013.01); C07F 7/10 (2013.01)] 18 Claims
 
1. A process, comprising
(i) combining an alkyl lithium and a compound having Formula II:

OG Complex Work Unit Chemistry
in a solvent at a temperature from about −20° C. to about −85° C. to give a first reaction mixture, wherein PG is a protecting group and LG1 is bromide or iodide;
(ii) adding ethylene oxide as is to said first reaction mixture at said temperature to give a second reaction mixture; and
(iii) adding a copper(I)salt to said second reaction mixture at said temperature to give a third reaction mixture comprising a compound having Formula III:

OG Complex Work Unit Chemistry