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Synthesis of [13 C6 ]-ibrutinib.

Michal Kriegelstein1, Miloš Hroch2, Aleš Marek1

  • 1Institute of Organic Chemistry and Biochemistry, The Czech Academy of Sciences, Prague, Czech Republic.

Journal of Labelled Compounds & Radiopharmaceuticals
|September 3, 2021
PubMed
Summary

A new method simplifies the synthesis of carbon-13 labeled ibrutinib, a crucial molecule for research. This efficient process introduces the isotope label late in the synthesis, improving the overall yield of the labeled compound.

Keywords:
[13C6]-ibrutinibcarbon-13cost-effective synthesisstable isotope labeling

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Isotope Labeling

Background:

  • Ibrutinib is a targeted therapy drug used in cancer treatment.
  • The synthesis of isotopically labeled compounds is essential for drug metabolism and pharmacokinetic studies.
  • Previous methods for synthesizing labeled ibrutinib may be complex or inefficient.

Purpose of the Study:

  • To develop a convenient and straightforward synthesis of carbon-13 labeled ibrutinib.
  • To provide a reliable method for producing [13C6]-ibrutinib for research purposes.

Main Methods:

  • The synthesis involved introducing a [13C6]-labeled building block in the final step of the reaction sequence.
  • The reaction sequence started from commercially available [13C6]-bromobenzene.

Main Results:

  • The study reports a convenient and straightforward synthesis of [13C6]-ibrutinib.
  • An isolated yield of 7% for [13C6]-ibrutinib was achieved, calculated from the starting material.
  • The late-stage introduction of the isotope-labeled building block proved effective.

Conclusions:

  • The developed method offers an efficient route to carbon-13 labeled ibrutinib.
  • This synthesis provides a valuable tool for researchers studying ibrutinib's behavior in biological systems.
  • The straightforward nature of the synthesis makes it suitable for broader application.