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Multigram‑scale synthesis of BTK inhibitor BIIB068.

Authors :
Jia, Donghao
Gu, Mingfang
Yu, Xinyue
Yuan, Kunyang
Wang, Sixuan
Guo, Mingzhang
Gong, Ping
Source :
Chemical Papers; Nov2023, Vol. 77 Issue 11, p6471-6481, 11p
Publication Year :
2023

Abstract

This paper describes the development of a relatively feasible, economic, and safe method for the multigram-scale synthesis of BIIB068, an efficient reversible BTK inhibitor. The new process is highlighted by an economical construction of a 2-amino-4 substituted pyrimidine employing a simple nucleophilic substitution reaction and a green reduction of the cyano group. The developed process provided an overall yield of 32%, with an HPLC purity of 99%. The structure of BIIB068 was confirmed by MS, IR, <superscript>1</superscript>H-NMR, and <superscript>13</superscript>C-NMR, and the structures of some intermediates were confirmed by MS and <superscript>1</superscript>H-NMR. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
03666352
Volume :
77
Issue :
11
Database :
Complementary Index
Journal :
Chemical Papers
Publication Type :
Academic Journal
Accession number :
172312744
Full Text :
https://doi.org/10.1007/s11696-023-02951-9