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Synthesis of N‐(4‐pyridyl[ 14 C]carbonylamino)‐1,2,[ 3 H]3,6‐tetrahydropyridine and the mono‐labelled [ 14 C]‐ and [ 3 H]‐analogues
Author(s) -
Mercer J. R.,
Wiebe L. I.,
Knaus E. E.
Publication year - 1981
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.2580180503
Subject(s) - chemistry , sodium borohydride , yield (engineering) , pyridinium , nuclear chemistry , chemical synthesis , solvent , medicinal chemistry , ethanol , organic chemistry , biochemistry , materials science , metallurgy , in vitro , catalysis
Reaction of isonicotinic [ 14 C] acid hydrazide ( 1 ) with the Zinke salt ( 2 ) afforded N‐(4‐pyridyl [ 14 C] carbonylimino)pyridinium ylide ( 3 ) in 81% chemical yield. Sodium borohydride reduction of 3 gave N‐(4‐pyridyl [ 14 C] carbonylamino) −1,2,3,6‐tetrahydropyridine ( 4 ) in 60% chemical yield with a specific activity of 6.17 mCi mM −1 . Alternatively reduction of N‐(4‐pyridylcarbonylimino) pyridinium ylide ( 5 ) using absolute ethanol and [ 3 H]‐water as solvent yielded N‐ (4‐pyridylcarbonylamino)‐1,2,[ 3 H]3,6‐tetrahydropyridine ( 9 ) in 52.6% chemical yield with a specific activity of 1.14 mCi mM −1 . N‐4‐Pyridyl[ 14 C]carbonylamino‐1,2,[ 3 H]3,6‐ tetrahydropyridine ( 10 ) was similarly prepared by sodium borohydride reduction of 3 using absolute ethanol and [ 3 H]‐water as solvent in 46% chemical yield with specific activities of 1.31 and 5.66 mCi mM −1 respectively for [ 3 H] and [ 14 C].