An Efficient Syntesis of 1,8-Naphthyridin-2(1H)-ones: Synthesis of Leukotriene Inhibitor SCH 37224

P. L. Nyce; D. Gala; M. Steinman

doi:10.1055/s-1991-26519

Synthesis 1991; 1991(7): 571-574
DOI: 10.1055/s-1991-26519

paper

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An Efficient Syntesis of 1,8-Naphthyridin-2(1H)-ones: Synthesis of Leukotriene Inhibitor SCH 37224

P. L. Nyce^* , D. Gala, M. Steinman

^*Chemical Process Research and Development, Schering Corporation, Bloomfield, NJ-07003, USA

Abstract

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A new, efficient synthesis of 1,8-naphthyridin-2(1H)-ones as applied to the synthesis of the leukotriene release inhibitor, 1,2-dihydro-1-phenyl-3-pyrrolidinio-2-oxo-1, 8-naphthyridin-4-olate inner salt (4) from methyl 2-phenylamino-3-pyridinecarboxylate, (1a), has been described. Towards this synthesis a new reaction procedure for the N-chloroacylation of 1a was developed. The high yield for the rest of the synthesis was obtained by establishing reaction conditions that utilized the solubility, and the stability properties 4.

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