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Optimisation of a key cross-coupling reaction towards the synthesis of a promising antileishmanial compound.

ABSTRACT: During the course of a research program aimed at identifying novel antileishmanial compounds, a multi-gram synthesis of N-(trans-4-((4-methoxy-3-((R)-3-methylmorpholino)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)cyclohexyl)-2-methylpropane-1-sulfonamide (( R )-1) was required. This letter describes optimisation of the reaction conditions and protecting group strategy for a key Buchwald-Hartwig coupling, delivering the required quantities of ( R )-1, as well as further compounds in the series.

SUBMITTER: Velasco RF

PROVIDER: S-EPMC6480136 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Optimisation of a key cross-coupling reaction towards the synthesis of a promising antileishmanial compound.

Velasco Raul F RF Guerrero César C Fra Gloria G Moure Alejandra A Miguel-Siles Juan J Quesada-Campos Maria Teresa MT Ruiz-Gomez Jose Ramon JR Gilbert Ian H IH Thomas Michael G MG Miles Timothy J TJ

Tetrahedron letters 20190501 18

During the course of a research program aimed at identifying novel antileishmanial compounds, a multi-gram synthesis of N-(trans-4-((4-methoxy-3-((R)-3-methylmorpholino)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)cyclohexyl)-2-methylpropane-1-sulfonamide (( R )-1) was required. This letter describes optimisation of the reaction conditions and protecting group strategy for a key Buchwald-Hartwig coupling, delivering the required quantities of ( ...[more]

PMID: 31057189

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