1408075-55-7Relevant academic research and scientific papers
The development of a new manufacturing route to the novel anticonvulsant, SB-406725A
Walker, Matthew D.,Andrews, Benjamin I.,Burton, Andrew J.,Humphreys, Luke D.,Kelly, Gary,Schilling, Mark B.,Scott, Peter W.
experimental part, p. 108 - 113 (2010/06/13)
The development of an efficient manufacturing route to 3-acetyl - N - (5,8-dichloro-1,2,3,4-tetrahydro-7-isoquinolinyl)-4-(1-methyl- ethoxy)-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 coupled with benzoate side chain (15) under base-promoted conditions using sodium hexamethyldisilazane to yield the parent molecule SB-406725 (16). SB-406725 was then converted to the HCl salt SB-406725A (1). This process has been successfully demonstrated on a pilot-plant scale to prepare ～30 kg of SB-406725A (1).
