Development of a scaleable synthesis of a 3-aminopyrazinone acetamide thrombin inhibitor

MS Ashwood, RJ Alabaster, IF Cottrell…

Index: Ashwood, Michael S.; Alabaster, Ramon J.; Cottrell, Ian F.; Cowden, Cameron J.; Davies, Antony J.; Dolling, Ulf H.; Emerson, Khateeta M.; Gibb, Andrew D.; Hands, David; Wallace, Debra J.; Wilson, Robert D. Organic Process Research and Development, 2004 , vol. 8, # 2 p. 192 - 200

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Citation Number: 6

Abstract

A scaleable route to 2-{3-[(2, 2-difluoro-2-(2-pyridyl) ethyl) amino]-6-chloro-2- oxohydropyrazinyl}-N-[(3-fluoro (2-pyridyl)) methyl] acetamide 1 is described in which various scaleup issues were addressed to provide a safe, efficient, and robust route for the preparation of multi-kilo amounts of the compound. The use of expensive and toxic reagents, notably sodium azide, TMS-cyanide, and Deoxo-Fluor, and the need for specialist ...