The Development of Practical Synthetic Routes to a CB2 Agonist: Efficient Construction of a Densely Substituted Purine Core

Autor:	Amy C. DeBaillie, Michael A. Staszak, Michael E. Laurila, Nicholas A. Magnus, Chauncey D. Jones
Rok vydání:	2013
Předmět:	Purine Active ingredient chemistry.chemical_compound chemistry Reagent Organic Chemistry Organic chemistry Amine gas treating Core (manufacturing) Physical and Theoretical Chemistry Cb2 agonist
Zdroj:	Organic Process Research & Development. 17:231-238
ISSN:	1520-586X 1083-6160
Popis:	An efficient and scalable process for the preparation of a purine-based CB2 agonist was developed. The production route to the requisite purine core relies on N-acylation and sequential substitution of a 5-amino-4,6-dichloropyrimidine with two amine building blocks followed by a cyclocondensation reaction. The chemistry was successfully employed to rapidly prepare over 5 kg of the active pharmaceutical ingredient. To further improve efficiencies, postproduction development resulted in a rearranged synthesis which reduced the need for pressure reactors and introduced the most costly reagent in the final step.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6f7e95e2c4bdb6a095149312fed45fd7 https://doi.org/10.1021/op300278c Zobrazit plný text záznamu