Process Development and Multikilogram-Scale Synthesis of a TRPV1 Antagonist

E Cleator, JP Scott, P Avalle, MM Bio…

文献索引：Cleator, Ed; Scott, Jeremy P.; Avalle, Paulo; Bio, Matthew M.; Brewer, Sarah E.; Davies, Antony J.; Gibb, Andrew D.; Sheen, Faye J.; Stewart, Gavin W.; Wallace, Debra J.; Wilson., Robert D. Organic Process Research and Development, 2013 , vol. 17, # 12 p. 1561 - 1567

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被引用次数: 1

摘要

The process development and multikilogram preparation of a TRPV1 antagonist, 1, is described. Pyrido [2, 3-b] pyrazine 1 was prepared in a convergent manner by the coupling of two key fragments, glyoxal 2 and diamine 3. Glyoxal 2 was synthesized in six chemical steps in 20% overall yield, the key step being a challenging Grignard reaction to install the glyoxalate moiety. Diamine 3 was also prepared in six chemical steps in 46% overall yield ...