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Related Concept Videos

¹H NMR of Labile Protons: Deuterium (²H) Substitution00:48

¹H NMR of Labile Protons: Deuterium (²H) Substitution

This lesson illustrates the role of deuterium substitution in simplifying the NMR spectrum of compounds comprising labile protons. One method employed is the use of deuterium. Amongst the three isotopes of hydrogen, deuterium (2H) has a nucleus composed of one proton and one neutron. When the D2O solvent is added to a pure dry ethanol solution, its labile proton is substituted with deuterium.

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Direct Multi-Deuterium Labelling of Pirtobrutinib.

Michal Kriegelstein1, Jana Hojcsková1, Miloš Hroch2

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

Journal of Labelled Compounds & Radiopharmaceuticals
|July 14, 2024
PubMed
Summary

This study presents an efficient method for multi-deuterium labeling of pirtobrutinib using hydrogen isotope exchange. High deuterium incorporation was achieved, yielding a stable isotope-labeled internal standard suitable for analytical applications.

Keywords:
HIESILISchlorobenzene labellingfluorine directing grouphydrogen isotope exchangepirtobrutinib‐d8solvent labelling

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Area of Science:

  • Chemical Synthesis
  • Medicinal Chemistry
  • Analytical Chemistry

Background:

  • Pirtobrutinib is a Bruton's tyrosine kinase inhibitor.
  • Stable isotope-labeled internal standards are crucial for quantitative analysis.
  • Efficient deuterium labeling methods are needed for pharmaceutical research.

Purpose of the Study:

  • To develop an efficient multi-deuterium labeling method for pirtobrutinib.
  • To produce a high-purity stable isotope-labeled pirtobrutinib (pirtobrutinib-d8) for use as an internal standard.
  • To investigate the role of fluorine as a directing group in hydrogen isotope exchange reactions.

Main Methods:

  • Hydrogen isotope exchange (HIE) reaction utilizing a Kerr-type iridium catalyst.
  • Employing a deuterium uniformly labeled solvent (chlorobenzene-d5) at elevated temperatures.
  • Purification and characterization of the labeled compound using mass spectrometry.

Main Results:

  • Achieved high deuterium incorporation (>87% in ortho-positions) in pirtobrutinib-d8.
  • The labeled compound consisted mainly of d6-d9 isotopomers (82.4% abundance).
  • Isolated pirtobrutinib-d8 in high yield (73%) and purity (99%), meeting internal standard requirements.
  • Observed fluorine's directing group effect for the first time in HIE reactions.
  • Non-specific deuteration of the chlorinated solvent was observed.

Conclusions:

  • The developed HIE method is efficient for multi-deuterium labeling of pirtobrutinib.
  • Pirtobrutinib-d8 is a suitable stable isotope-labeled internal standard.
  • The study provides new insights into directing group effects in HIE reactions.