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Synfacts 2011(8): 0816-0816  
DOI: 10.1055/s-0030-1260680
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of GSK1842799

Contributor(s): Philip Kocienski
M. S. Anson, J. P. Graham*, A. J. Roberts
GlaxoSmithKline Research and Development Ltd., Stevenage, UK
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Publication History

Publication Date:
20 July 2011 (online)

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Significance

GSK1842799 is a sphingosine-1-phosphate receptor subtype 1 (S1P1) agonist with potential for the treatment of transplant rejection and autoimmune diseases, such as psoriasis and multiple sclerosis. Key features in the synthesis ­include (1) a nucleophilic aromatic substitution to install a lipophilic 1-octyloxy chain (A → B) and (2) the use of Lawesson’s reagent to form the thiadi­azole ring (F) from diacyl hydrazide E. Owing to the absence of crystalline intermediates, none of the ­intermediates were purified.