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Synthesis and HPLC‐purification of [ 77 Br]TMC125‐R165335 (etravirine), a new anti‐HIV drug of the DAPY‐NNRTI class
Author(s) -
Spiegeleer Bart De,
Dumont Filip,
Peremans Kathelijne,
Burvenich Christian,
Van Vooren Lieven,
Rosier Jan,
Baert Lieven,
Wigerinck Piet,
Slegers Guido
Publication year - 2006
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1085
Subject(s) - chemistry , etravirine , oxidizing agent , bromine , aqueous solution , electrophile , high performance liquid chromatography , yield (engineering) , solvent , labelling , ethanol , radiochemistry , organic chemistry , chromatography , nuclear chemistry , biochemistry , reverse transcriptase , rna , materials science , metallurgy , gene , catalysis
[ 77 Br]TMC125‐R165335 (etravirine) was synthesized for imaging studies by SPECT. Labelling was performed with bromine‐77 by electrophilic substitution of the desbromo‐precursor 4‐{6‐amino‐2‐[(4‐cyanophenyl)amino]pyrimidin‐4‐yloxy}‐3,5‐dimethylbenzenecarbonitrile using carrier‐free 77 Br − and chloramine‐T (CAT) as oxidizing agent. The reaction proceeded in 10 min at room temperature in aqueous DMSO as solvent. Purification was performed by HPLC, giving a chemically and radiochemically pure [ 77 Br]TMC125‐R165335 (etravirine) in aqueous ethanol. A final radiolabelling yield of 50% is obtained. Copyright © 2006 John Wiley & Sons, Ltd.
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