Synthesis of 2,6-difluoro-N-(3-[11C]methoxy-1H-pyrazolo[3,4-b] pyridine-5-yl)-3-(propylsulfonamidio)benzamide as a new potential PET agent for imaging of B-RafV600E in cancers

Min Wang, Mingzhang Gao, Kathy D. Miller, Qi Huang Zheng

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

The authentic standard 2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b] pyridine-5-yl)-3-(propylsulfonamidio)benzamide was synthesized from 2,6-difluorobenzoic acid and 3-amino-5-hydroxypyrazole in 9 steps with 1% overall chemical yield. Direct desmethylation of the reference standard with TMSCl/NaI gave the precursor 2,6-difluoro-N-(3-hydroxy-1H-pyrazolo[3,4-b] pyridine-5-yl)-3-(propylsulfonamidio)benzamide for radiolabeling in 70% yield. The target tracer 2,6-difluoro-N-(3-[11C]methoxy-1H-pyrazolo[3,4-b] pyridine-5-yl)-3-(propylsulfonamidio)benzamide was prepared from the precursor with [11C]CH3OTf through O-[11C]methylation and isolated by HPLC combined with SPE in 40-50% decay corrected radiochemical yields with 370-740 GBq/μmol specific activity at end of bombardment (EOB).

Original languageEnglish (US)
Pages (from-to)1017-1021
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume23
Issue number4
DOIs
StatePublished - Feb 15 2013

Keywords

  • 2,6-Difluoro-N-(3-[C]methoxy-1H-pyrazolo[3,4-b]pyridine-5-yl)- 3-(propylsulfonamidio)benzamide ([C]9)
  • Automation
  • B-Raf
  • Cancer imaging
  • Positron emission tomography (PET)
  • Radiosynthesis

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

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