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Practical Synthesis of 7-Bromo-4-chloro-1H-indazol-3-amine: An Important Intermediate to Lenacapavir.
Asad, Naeem; Lyons, Michael; Muniz Machado Rodrigues, Shirley; Burns, Justina M; Roper, Thomas D; Laidlaw, G Michael; Ahmad, Saeed; Gupton, B Frank; Klumpp, Douglas; Jin, Limei.
Afiliação
  • Asad N; Medicines for All Institute, Virginia Commonwealth University, Richmond, VA 23284-3068, USA.
  • Lyons M; Medicines for All Institute, Virginia Commonwealth University, Richmond, VA 23284-3068, USA.
  • Muniz Machado Rodrigues S; Medicines for All Institute, Virginia Commonwealth University, Richmond, VA 23284-3068, USA.
  • Burns JM; Medicines for All Institute, Virginia Commonwealth University, Richmond, VA 23284-3068, USA.
  • Roper TD; Medicines for All Institute, Virginia Commonwealth University, Richmond, VA 23284-3068, USA.
  • Laidlaw GM; Medicines for All Institute, Virginia Commonwealth University, Richmond, VA 23284-3068, USA.
  • Ahmad S; Medicines for All Institute, Virginia Commonwealth University, Richmond, VA 23284-3068, USA.
  • Gupton BF; Medicines for All Institute, Virginia Commonwealth University, Richmond, VA 23284-3068, USA.
  • Klumpp D; Medicines for All Institute, Virginia Commonwealth University, Richmond, VA 23284-3068, USA.
  • Jin L; Medicines for All Institute, Virginia Commonwealth University, Richmond, VA 23284-3068, USA.
Molecules ; 29(12)2024 Jun 07.
Article em En | MEDLINE | ID: mdl-38930779
ABSTRACT
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.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Molecules Assunto da revista: BIOLOGIA Ano de publicação: 2024 Tipo de documento: Article País de afiliação: Estados Unidos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Molecules Assunto da revista: BIOLOGIA Ano de publicação: 2024 Tipo de documento: Article País de afiliação: Estados Unidos