Observation of differential reactivity of cyclic amines in S(N)2 and SNAr displacement reactions in the course of synthesizing C-6, C-7 substituted quinolinecarbonitrile MEK1 kinase inhibitors

We have previously reported on a series of 4-anilino-6,7-dialkoxy-3-quinolinecarbonitriles as potent inhibitors of MEK1 kinase. Herein, we describe our synthetic efforts toward a series of 4-anilino-6-allcoxy-7-amino-3-quinolinecarbonitriles. In the course of this work, we were able to rapidly const...

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Bibliographic Details
Published inTetrahedron letters Vol. 49; no. 1; pp. 137 - 140
Main Authors Hopper, Darrin W., Dutia, Minu, Berger, Dan M., Powell, Dennis W.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.2008
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:We have previously reported on a series of 4-anilino-6,7-dialkoxy-3-quinolinecarbonitriles as potent inhibitors of MEK1 kinase. Herein, we describe our synthetic efforts toward a series of 4-anilino-6-allcoxy-7-amino-3-quinolinecarbonitriles. In the course of this work, we were able to rapidly construct a library of 4-anilino-6-alkoxy-7-amino-3-quinolinecarbonitriles by simultaneous or sequential S(N)2 (displacement) reactions on the C-6 chloroalkoxy moiety and SNAr (addition/elimination) reactions at C-7 with nucleophilic amines. (c) 2007 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2007.10.151