Optimisation of a Key Cross-Coupling Reaction Towards the Synthesis of a Promising Antileishmanial Compound

Raul F. Velasco, César Guerrero, Gloria Fra, Alejandra Moure, Juan Miguel-Siles, Maria Teresa Quesada-Campos, Jose Ramon Ruiz-Gomez, Ian H. Gilbert, Michael G. Thomas (Lead / Corresponding author), Timothy J. Miles (Lead / Corresponding author)

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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.
Original languageEnglish
Pages (from-to)1243-1247
Number of pages5
JournalTetrahedron Letters
Volume60
Issue number18
Early online date28 Mar 2019
DOIs
Publication statusPublished - 2 May 2019

Keywords

  • 2-(Trimethylsilyl)ethoxymethyl (SEM)
  • Buchwald-Hartwig coupling
  • Protecting group strategy
  • Visceral leishmaniasis

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    Velasco, R. F., Guerrero, C., Fra, G., Moure, A., Miguel-Siles, J., Quesada-Campos, M. T., Ruiz-Gomez, J. R., Gilbert, I. H., Thomas, M. G., & Miles, T. J. (2019). Optimisation of a Key Cross-Coupling Reaction Towards the Synthesis of a Promising Antileishmanial Compound. Tetrahedron Letters, 60(18), 1243-1247. https://doi.org/10.1016/j.tetlet.2019.03.068