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Newcastle Upon Tyne, United Kingdom

Gautier F.-M.,University of Sheffield | Jones S.,University of Sheffield | Li X.,University of Sheffield | Martin S.J.,Aesica Pharmaceuticals
Organic and Biomolecular Chemistry

A highly active organocatalyst has been shown to affect the asymmetric reductive amination of ketones producing both aromatic and aliphatic amines. At 1 mol% catalyst loading, a series of structurally diverse chiral amines were quickly and economically prepared with good enantioselectivity and generally useful yield. The efficient synthesis of the calcimimetic (+)-NPS R-568 (67%, 89% ee) demonstrated the synthetic applicability of this methodology. © 2011 The Royal Society of Chemistry. Source

Dubois N.,University of Nottingham | Glynn D.,University of Nottingham | McInally T.,University of Nottingham | Rhodes B.,Aesica Pharmaceuticals | And 3 more authors.

The range and utility of DABAL-Me3 couplings of methyl esters and free carboxylic acids with primary and secondary amines under a variety of conditions (reflux, sealed tube, microwave) has been compared for a significant range of coupling partners of relevance to the preparation of amides of interest in pharmaceutical chemistry. Commercial microwave reactors promote the fastest couplings and allow the use of significantly sterically hindered amines (primary and secondary) and carboxylic acids derivatives. The influence of microwave energy on the reaction system was shown to be typically related to thermal effects (over-pressuring and superheating). © 2013 Elsevier Ltd. All rights reserved. Source

Aesica Pharmaceuticals | Date: 2012-02-21

Pharmaceutical preparations for the treatment of inflammation, arthritis, dementia, cancer, pain or mood disorders, such as, anxiety, depression and dysthymia.

Lee D.S.,University of Nottingham | Amara Z.,University of Nottingham | Poliakoff M.,University of Nottingham | Harman T.,Aesica Pharmaceuticals | And 5 more authors.
Organic Process Research and Development

Methods for the batch scale up of DABAL-Me3 promoted direct ester to amide synthesis have been demonstrated at 10-100 g scales using a tert-amide model compound. Procedures for 20 g scale couplings in standard laboratory glassware and up to 0.1 kg in industry-standard jacketed glass reactors in near quantitative yields are given. A derivative of the anticancer agent Imatinib (Gleevec) has been synthesized on a 26 g scale (98% yield, >98% purity) establishing DABAL-Me3 as a potential alternative for the synthesis of amides in API scale preparations. Continuous flow methodology provides a method for larger scales (productivities of >50 g h-1). In addition, nitriles were coupled to primary amines and hydrazines with DABAL-Me3, resulting in the clean formation of free amidines (16 examples) and amidrazones. © 2015 American Chemical Society. Source

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