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Synthesis 2003(11): 1712-1716
DOI: 10.1055/s-2003-40872
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Synthesis of a Potent Src Kinase Inhibitor: 4-(2,4-Dichloro-5-methoxyphenylamino)-7-methoxy-8-(2-morpholin-4-ylethoxy)benzo[g]quinoline-3-carbonitrile

Dan M. Berger*, Gary Birnberg, Frenel DeMorin, Minu Dutia, Dennis Powell, Yanong D. Wang
Chemical Sciences, Wyeth Research, 401 N. Middletown Rd, Pearl River, NY 10965, USA
Fax: +1(845)6025561; e-Mail: bergerd@wyeth.com;
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Publication History

Received 28 April 2003
Publication Date:
25 July 2003 (online)

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Abstract

The regioselective synthesis of compound 3, a potent Src kinase inhibitor is described. A key step in this synthesis is the regio­selective thermal rearrangement of a substituted benzocyclobutene to provide a 2,3,6,7-tetrasubstituted naphthalene. An efficient route to the uniquely substituted benzocyclobutene is reported.

Key words

drugs - regioselectivity - rearrangements - heterocycles - ring closure

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Boschelli, F.; Weber, J. M.; Lucas, J.; Etienne, C.; Arndt, K.; Gibbons, J.; Boschelli, D. H.; Dutia, M.; Powell, D.; Wu, B.; Yaczko, D.; Ye, F. 93rd Annual Meeting of the American Association of Cancer Research; San Francisco: CA, 2002, Abstract 4206.

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Berger, D.; Dutia, M.; Birnberg, G.; DeMorin, F.; Powell, D.; Wang, Y. D.; Boschelli, D. H.; Ye, F.; Golas, J. M.; Boschelli, F. J. Med. Chem., manuscript in preparation.