Convenient efficient synthesis of TAK-779, a nonpeptide CCR5 antagonist: development of preparation of various ammonium salts using trialkylphosphiteand N-halogenosuccinimide

Authors
Ikemoto, T Nishiguchi, A Mitsudera, H Wakimasu, M Tomimatsu, K
Citation
T. Ikemoto et al., Convenient efficient synthesis of TAK-779, a nonpeptide CCR5 antagonist: development of preparation of various ammonium salts using trialkylphosphiteand N-halogenosuccinimide, TETRAHEDRON, 57(8), 2001, pp. 1525-1529
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
8
Year of publication
2001
Pages
1525 - 1529
Database
ISI
SICI code
0040-4020(20010218)57:8<1525:CESOTA>2.0.ZU;2-2
Abstract
A convenient and efficient synthesis of TAK-779 (1a), a nonpeptide CCR5 ant agonist, has been achieved. The new methylation of tertiary amine (2) using trimethyl phosphite and N-chlorosuccinimide. followed by the addition of H Cl led to ammonium chloride (1a) in 89% isolated yield without requiring a chromatographic method. By this preparation. ammonium methanesulfonate (le) could be obtained in 75% isolated yield. (C) 2001 Elsevier Science Ltd. All rights reserved.