NDLI: Self-optimisation of the final stage in the synthesis of EGFR kinase inhibitor AZD9291 using an automated flow reactor

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Towards scalable and controlled synthesis of metal–organic framework materials using continuous flow reactors

Monolith-based ⁶⁸Ga processing: a new strategy for purification to facilitate direct radiolabelling methods

Self-optimisation of the final stage in the synthesis of EGFR kinase inhibitor AZD9291 using an automated flow reactor

Application of online infrared spectroscopy to study the kinetics of precipitation polymerization of acrylic acid in supercritical carbon dioxide

Continuous flow synthesis of the iodination agent 1,3-diiodo-5,5-dimethyl-imidazolidine-2,4-dione telescoped with semi-continuous product isolation

Selectivity engineering of the diazotization reaction in a continuous flow reactor

Gas–solid conversion of lignin to carboxylic acids

Catalytic distillation for ethyl acetate synthesis using microfibrous-structured Nafion–SiO₂/SS-fiber solid acid packings

Application of microfluidics to control product selectivity during non-catalytic oxidation of naphthenic-aromatic hydrocarbons

Continuous flow synthesis concatenated with continuous flow liquid–liquid extraction for work-up and purification: selective mono- and di-iodination of the imidazole backbone

Hydrogenation of 2-methyl-3-butyn-2-ol over a Pd/ZnO catalyst: kinetic model and selectivity study

Structuring hybrid palladium nanoparticles in metallic monolithic reactors for continuous-flow three-phase alkyne hydrogenation

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Self-optimisation of the final stage in the synthesis of EGFR kinase inhibitor AZD9291 using an automated flow reactor

Content Provider	Royal Society of Chemistry (RSC)
Author	Akien, Geoffrey R. Woodward, Robert L. Holmes, Nicholas Bourne, Richard A. Meadows, Rebecca E. Blacker, A. John
Copyright Year	2016
Abstract	Self-optimising flow reactors combine online analysis with evolutionary feedback algorithms to rapidly achieve optimum conditions. This technique has been applied to the final bond-forming step in the synthesis of AZD9291, an irreversible epidermal growth factor receptor kinase inhibitor developed by AstraZeneca. A four parameter optimisation of a telescoped amide coupling followed by an elimination reaction was achieved using at-line high performance liquid chromatography. Optimisations were initially carried out on a model compound (2,4-dimethoxyaniline) and the data used to track the formation of various impurities and ultimately propose a mechanism for their formation. Our protocol could then be applied to the optimisation of the 2-step telescoped reaction to synthesise AZD9291 in 89% yield.
Starting Page	366
Ending Page	371
Page Count	6
File Format	HTM / HTML PDF
ISSN	20589883
Volume Number	1
Issue Number	4
Journal	Reaction Chemistry & Engineering
DOI	10.1039/c6re00059b
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Osimertinib Amide AstraZeneca Protein kinase inhibitor High-performance liquid chromatography Elimination reaction Growth factor 2-step garage
Content Type	Text
Resource Type	Article
Subject	Chemistry Fluid Flow and Transfer Processes Catalysis Process Chemistry and Technology

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Online quantitative mass spectrometry for the rapid adaptive optimisation of automated flow reactors

Liquid chromatography-tandem mass spectrometric assay for the T790M mutant EGFR inhibitor osimertinib (AZD9291) in human plasma.

Osimertinib (AZD9291), a Mutant-Selective EGFR Inhibitor, Reverses ABCB1-Mediated Drug Resistance in Cancer Cells

Clinical activity of the EGFR tyrosine kinase inhibitor osimertinib in EGFR-mutant glioblastoma.

Online monitoring and analysis for autonomous continuous flow self-optimizing reactor systems

Kinetics analysis and automated online screening of aminocarbonylation of aryl halides in flow

Reversion of mesenchymal behaviour by AZD9291 (osimertinib) in EGFR mutant NSCLC cell lines resistant to first generation EGFR tyrosine kinase inhibitors

Engineering chemistry: integrating batch and flow reactions on a single, automated reactor platform

Osimertinib making a breakthrough in lung cancer targeted therapy

Self-optimisation of the final stage in the synthesis of EGFR kinase inhibitor AZD9291 using an automated flow reactor

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Online quantitative mass spectrometry for the rapid adaptive optimisation of automated flow reactors

Liquid chromatography-tandem mass spectrometric assay for the T790M mutant EGFR inhibitor osimertinib (AZD9291) in human plasma.

Osimertinib (AZD9291), a Mutant-Selective EGFR Inhibitor, Reverses ABCB1-Mediated Drug Resistance in Cancer Cells

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Osimertinib making a breakthrough in lung cancer targeted therapy

Self-optimisation of the final stage in the synthesis of EGFR kinase inhibitor AZD9291 using an automated flow reactor