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

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Keywords

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

Cite this

Velasco, R. F., Guerrero, C., Fra, G., Moure, A., Miguel-Siles, J., Quesada-Campos, M. T., ... 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
Velasco, Raul F. ; Guerrero, César ; Fra, Gloria ; Moure, Alejandra ; Miguel-Siles, Juan ; Quesada-Campos, Maria Teresa ; Ruiz-Gomez, Jose Ramon ; Gilbert, Ian H. ; Thomas, Michael G. ; Miles, Timothy J. / Optimisation of a Key Cross-Coupling Reaction Towards the Synthesis of a Promising Antileishmanial Compound. In: Tetrahedron Letters. 2019 ; Vol. 60, No. 18. pp. 1243-1247.
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Velasco, RF, Guerrero, C, Fra, G, Moure, A, Miguel-Siles, J, Quesada-Campos, MT, Ruiz-Gomez, JR, Gilbert, IH, Thomas, MG & Miles, TJ 2019, 'Optimisation of a Key Cross-Coupling Reaction Towards the Synthesis of a Promising Antileishmanial Compound', Tetrahedron Letters, vol. 60, no. 18, pp. 1243-1247. https://doi.org/10.1016/j.tetlet.2019.03.068

Optimisation of a Key Cross-Coupling Reaction Towards the Synthesis of a Promising Antileishmanial Compound. / Velasco, Raul F.; Guerrero, César; Fra, Gloria; Moure, Alejandra; Miguel-Siles, Juan; Quesada-Campos, Maria Teresa; Ruiz-Gomez, Jose Ramon; Gilbert, Ian H.; Thomas, Michael G. (Lead / Corresponding author); Miles, Timothy J. (Lead / Corresponding author).

In: Tetrahedron Letters, Vol. 60, No. 18, 02.05.2019, p. 1243-1247.

Research output: Contribution to journalArticle

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AU - Velasco, Raul F.

AU - Guerrero, César

AU - Fra, Gloria

AU - Moure, Alejandra

AU - Miguel-Siles, Juan

AU - Quesada-Campos, Maria Teresa

AU - Ruiz-Gomez, Jose Ramon

AU - Gilbert, Ian H.

AU - Thomas, Michael G.

AU - Miles, Timothy J.

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Velasco RF, Guerrero C, Fra G, Moure A, Miguel-Siles J, Quesada-Campos MT et al. Optimisation of a Key Cross-Coupling Reaction Towards the Synthesis of a Promising Antileishmanial Compound. Tetrahedron Letters. 2019 May 2;60(18):1243-1247. https://doi.org/10.1016/j.tetlet.2019.03.068