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The syntheses of radiolabelled org 5222 and its main metabolite org 30526
Author(s) -
Vader Jan,
Kaspersen Frans,
Sperling Eric,
Schlachter Irene,
Terpstra Annie,
Hilberink Peter,
Wagenaars Gerard
Publication year - 1994
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.2580340907
Subject(s) - chemistry , halogenation , sarcosine , metabolite , amide , catalysis , medicinal chemistry , demethylation , pyrrole , stereochemistry , organic chemistry , amino acid , glycine , biochemistry , gene expression , dna methylation , gene
The syntheses of trans‐5‐chloro‐2, 3, 3a‐12b‐tetrahydro‐2‐methyl‐1H‐dibenz [2, 3:6, 7] oxepino [4, 5‐c]pyrrole (Org 5222), a potential antipsychotic compound, labelled with 3 H, 14 C and 36 C1 and trans‐5‐chloro‐2, 3, 3a, 12b‐tetrahydro‐1H‐dibenz [2, 3:6, 7]‐oxepino [4, 5‐c] pyrrole (Org 30526) labelled with 3 H are described. 3 H‐labelled Org 5222 of low specific activity was prepared by a base catalyzed exchange with tritiated water of an amide precursor, 3 H‐labelled Org 5222 with a high specific activity by a catalytic reductive dehalogenation. 3 H‐labelled Org 30526 was prepared both by demethylation of 3 H‐Org 5222 and by catalytic reductive iodination of 11‐iodo‐Org 30526. 14 C‐labelled Org 5222 was synthesized in 6 steps using 14 C‐sarcosine as starting material. 36 C1‐labelled Org 5222 was prepared by diazotation reaction in the presence of H 36 C1.