The Development of a New Manufacturing Route to the Novel Anticonvulsant, SB-406725A

…, BI Andrews, AJ Burton, LD Humphreys…

Index: Walker, Matthew D.; Andrews, Benjamin I.; Burton, Andrew J.; Humphreys, Luke D.; Kelly, Gary; Schilling, Mark B.; Scott, Peter W. Organic Process Research and Development, 2010 , vol. 14, # 1 p. 108 - 113

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Citation Number: 5

Abstract

The development of an efficient manufacturing route to 3-acetyl-N-(5, 8-dichloro-1, 2, 3, 4- tetrahydro-7-isoquinolinyl)-4-(1-methylethoxy)-benzamide hydrochloride SB-406725A (1) is described. The synthesis begins with dichlorination of isoquinoline, followed by nitration using nitronium tetrafluoroborate in sulpholane. Nitroisoquinoline (12) was hydrogenated under pressure using Pt/C. The resultant tetrahydroisoquinoline (13) was selectively ...