Practical Synthesis of 7-Bromo-4-chloro-1H-indazol-3-amine: An Important Intermediate to Lenacapavir

Autor:	Naeem Asad, Michael Lyons, Shirley Muniz Machado Rodrigues, Justina M. Burns, Thomas D. Roper, G. Michael Laidlaw, Saeed Ahmad, B. Frank Gupton, Douglas Klumpp, Limei Jin
Jazyk:	angličtina
Rok vydání:	2024
Předmět:	Lenacapavir indazol-3-amine hydrazine regioselective cyclization process development Organic chemistry QD241-441
Zdroj:	Molecules, Vol 29, Iss 12, p 2705 (2024)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules29122705
Popis:	7-Bromo-4-chloro-1H-indazol-3-amine is a heterocyclic fragment used in the synthesis of Lenacapavir, a potent capsid inhibitor for the treatment of HIV-1 infections. In this manuscript, we describe a new approach to synthesizing 7-bromo-4-chloro-1H-indazol-3-amine from inexpensive 2,6-dichlorobenzonitrile. This synthetic method utilizes a two-step sequence including regioselective bromination and heterocycle formation with hydrazine to give the desired product in an overall isolated yield of 38–45%. The new protocol has been successfully demonstrated on hundred-gram scales without the need for column chromatography purification. This new synthesis provides a potential economical route to the large-scale production of this heterocyclic fragment of Lenacapavir.
Databáze:	Directory of Open Access Journals
Externí odkaz:	https://doaj.org/article/58370c2cdc4b470395e7f1bfe475e816 Zobrazit plný text záznamu View record in DOAJ Plný text ve formátu PDF Plný text ve formátu HTML
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