Solid phase and combinatorial synthesis of substituted 2-methyle

Details Solid phase and combinatorial synthesis of substituted 2-methyle Solid phase and combinatorial synthesis of substituted 2-methyle

1997-04-16

1998-12-08

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548187, 544367, C07D27714

Patent

active

058471502

ABSTRACT:
A solid phase method for the synthesis of a plurality of differently substituted 2-methylenethiazoles with a wide variety of side-chain substituents as compounds of potential therapeutic interest. The 2-methylenethiazoles are prepared by acylation of a substrate-bound primary or secondary amine with cyanoacetic acid and reaction of the resulting cyanoacetamide with an isothiocyanate in the presence of a base. Alkylation with an appropriate alkyl halide under acidic conditions yields differently substituted, support-bound 2-methylene-2,3-dihydrothiazoles. These may be screened on the substrate or cleaved from the substrate and then screened in solution. The efficient synthesis of a wide variety of 2-methylenethiazoles using automated synthesis technology of the present method makes these compounds attractive candidates for the generation and rapid screening of diverse thiazole-based libraries. The method disclosed here provides an easy and fast access to highly diverse heterocyclic compounds of therapeutic interest, amenable to automatization.

REFERENCES:
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F. Zaragoza, Tetrahedron Letters, vol. 36, No. 47, pp. 8677-8678 (1995).
E.R. Felder, Chimia, vol. 48, pp. 531-541, (1994).
E.M. Gordon, Current Biology Ltd., vol. 6, pp. 624-631 (1995).
Fruchtel et al., Angew Chem. Int. Ed., vol. 35, pp. 17-42, (1996).

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