Process development and large-scale synthesis of a PDE4 inhibitor

DA Conlon, A Drahus-Paone, GJ Ho…

文献索引：Conlon, David A.; Drahus-Paone, Antoinette; Ho, Guo-Jie; Pipik, Brenda; Helmy, Roy; McNamara, James M.; Shi, Yao-Jun; Williams, J. Michael; Macdonald, Dwight; Deschenes, Denis; Gallant, Michel; Mastracchio, Anthony; Roy, Bruno; Scheigetz, John Organic Process Research and Development, 2006 , vol. 10, # 1 p. 36 - 45

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被引用次数: 30

摘要

An efficient, scalable synthesis of the PDE4 inhibitor, 6-[1-methyl-1-(methylsulfonyl) ethyl]-8- (3-{(E)-2-(3-methyl-1, 2, 4-oxadiazol-5-yl)-2-[4-(methylsulfonyl) phenyl] vinyl} phenyl) quinoline benzenesulfonate (10) is described. The synthesis is highly convergent, generating the penultimate 9 by coupling aldehyde 7 and oxadiazole 8 in a Knoevenagel reaction. The process consists of a total of nine chemical steps, five of which comprise the ...