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Radiosynthesis of N-[4-(4-fluorobenzyl)piperidin-1-yl]-N′-(2-[11C]oxo-1,3-dihydrobenzimidazol-5-yl)oxamide, a NR2B-selective NMDA receptor antagonist

✍ Scribed by Romain Labas; Franck Sobrio; Yann Bramoullé; Anne-Sophie Hérard; Martine Guillermier; Philippe Hantraye; Frédéric Dollé; Louisa Barré

Publisher
John Wiley and Sons
Year
2009
Tongue
French
Weight
136 KB
Volume
53
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

In order to perform in vivo imaging of the NR2B NMDA receptor system by positron emission tomography, a NR2B selective NMDA receptor antagonist has been labelled with carbon‐11 (half‐life: 20 min). N‐[4‐(4‐fluorobenzyl)piperidin‐1‐yl]‐N′‐(2‐oxo‐1,3‐dihydrobenzimidazol‐5‐yl)oxamide has been described demonstrating high affinity and selectivity for the NR2B receptors (IC~50~ of 5 nM in [^3^H]Ro‐25,6981 binding assay). The labelling precursor and the reference compound were synthesized by coupling the 4‐(4‐fluorobenzyl)piperidine with the corresponding oxalamic acid. The reaction of [^11^C]phosgene with phenylenediamine precursor led the formation of the [^11^C]benzimidazolone ring present on the ligand. The labelling occurred in THF or acetonitrile and the decay corrected radiochemical yield was 30–40% from the produced [^11^C]methane. HPLC purification and formulation led to 2.6–3.7 GBq (70–100 mCi) of radioligand within 30–35 min. The specific radioactivity was 72–127 GBq/µmol (2–3.4 Ci/µmol) at the end of synthesis. Copyright © 2009 John Wiley & Sons, Ltd.

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