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Access to drug metabolites via C-H functionalization: Copper-catalyzed aerobic oxidation of N,N-dimethylalkylamines in complex pharmaceuticals

Sames, Dalibor and Genovino, Julien (2014) Access to drug metabolites via C-H functionalization: Copper-catalyzed aerobic oxidation of N,N-dimethylalkylamines in complex pharmaceuticals. Tetrahedron Letters, 56 (23). pp. 3066-3069. ISSN 1873-3581

Abstract

We aim the power of C-H bond functionalization at a problem of major practical consequence-namely, scalable access to drug metabolites and their analogs. In this context, we pursue the development of simple C-H oxidation methods that tolerate a wide range of functional groups and structural features found in pharmaceuticals ('chemotransformations'). In this Letter, we focus on N,. N-dimethylamines as they are frequently found in pharmaceuticals and undergo CYP-mediated N-demethylation reactions in vivo. The direct access to these in vivo metabolites, from the parent drugs, has remained a significant synthetic challenge for which a broad solution had not previously been found. We here show that a simple copper-oxygen catalytic system provides a scalable route to complex N-demethylated drug metabolites.

Item Type: Article
Keywords: Aerobic oxidation C-H oxidation Copper-catalysis CYP450 Drug metabolism In vivo metabolites
Date Deposited: 29 Nov 2017 00:45
Last Modified: 25 Jan 2019 00:46
URI: https://oak.novartis.com/id/eprint/21490

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