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Development of a practical synthesis of toll-like receptor agonist PF-4171455: 4-Amino-1-benzyl-6-trifluoromethyl-1,3-dihydroimidazo [4,5-c] pyridin-2-one

Adam, Fiona M., Bish, Gerwyn, Calo, Frederick, Carr, Christopher L., Castro, Nieves, Hay, Duncan, Hodgson, Paul B., Jones, Peter, Knight, Craig J., Paradowski, Michael, Parsons, Gemma C., Proctor, Katie J. W., Pryde, David C., Rota, Filippo, Smith, Mya C., Smith, Nicholas, Tran, Thien-Duc, Hitchin, James and Dixon, Rachel 2011. Development of a practical synthesis of toll-like receptor agonist PF-4171455: 4-Amino-1-benzyl-6-trifluoromethyl-1,3-dihydroimidazo [4,5-c] pyridin-2-one. Organic Process Research and Development 15 (4) , pp. 788-796. 10.1021/op200021a

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Abstract

The development and implementation of a scalable process for the manufacture of the Toll-like receptor (TLR7) agonist PF-4171455 (1) is described. Initial routes used to synthesise 1 in milligram quantities were unsuitable for large-scale synthesis to provide bulk material. As part of the transfer between Medicinal Chemistry and Research-API, collaboration provided a fit for purpose route for the kilo-scale synthesis of 1. Key aspects of the synthesis included (i) a safe and practical synthesis of a key nitropyridone intermediate 7 over four steps, (ii) a sequential regioselective chlorination to selectively functionalise 7 and (iii) use of a carbamate as a tethered carbonyl group, allowing an efficient regiospecific synthesis of 1.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Biosciences
Publisher: ACS
ISSN: 1083-6160
Last Modified: 14 Dec 2017 15:31
URI: http://orca-mwe.cf.ac.uk/id/eprint/107378

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