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

被引：2

作者：

Velasco, Raul F. ^{[1
]}

Guerrero, Cesar ^{[1
]}

Fra, Gloria ^{[1
]}

Moure, Alejandra ^{[1
]}

Miguel-Siles, Juan ^{[2
]}

Teresa Quesada-Campos, Maria ^{[2
]}

Ramon Ruiz-Gomez, Jose ^{[2
]}

Gilbert, Ian H. ^{[3
]}

Thomas, Michael G. ^{[3
]}

Miles, Timothy J. ^{[2
]}

机构：

[1] GalChimia SA, Cebreiro S-N, O Pino 15823, A Coruna, Spain

[2] GlaxoSmithKline, Global Hlth R&D, Calle Severo Ochoa 2, Madrid 28760, Spain

[3] Univ Dundee, Sch Life Sci, Div Biol Chem & Drug Discovery, Wellcome Ctr Antiinfect Res,Drug Discovery Unit, Dundee DD1 5EH, Scotland

来源：

TETRAHEDRON LETTERS | 2019年 / 60卷 / 18期

关键词：

Buchwald-Hartwig coupling; Protecting group strategy; Visceral leishmaniasis; 2-(Trimethylsilyl)ethoxymethyl (SEM); C-C; PRECATALYSTS;

D O I：

10.1016/j.tetlet.2019.03.068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

During the course of a research program aimed at identifying novel antileishmanial compounds, a multi gram synthesis of N-(trans-44(4-methoxy-34(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. Crown Copyright (C) 2019 Published by Elsevier Ltd.

引用

页码：1243 / 1247

页数：5

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