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Synthesis of ( R )‐5‐(Di[2,3‐ 3 H 2 ]propylamino)5,6‐dihydro‐4 H ‐imidazo[4,5,1‐ ij ]quinolin‐2(1 H )‐one ([ 3 H]U‐86170) and ( R )‐5‐([2,3‐ 3 H 2 ]Propylamino)‐5,6‐dihydro‐4 H ‐imidazo[4,5,1‐ ij ]quinolin‐2(1 H )‐one ([ 3 H]U‐91356)
Author(s) -
Moon Malcolm W.,
Hsi Richard S. P.
Publication year - 1992
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.2580311112
Subject(s) - chemistry , agonist , yield (engineering) , medicinal chemistry , radioligand , stereochemistry , tritium , receptor , biochemistry , materials science , physics , nuclear physics , metallurgy
( R )‐5‐(diallylamino)‐5,6‐dihydro‐4 H ‐imidazo[4,5,1‐ ij ]quinolin‐2(1 H )‐one ( 12b ) was prepared in 9% overall yield from 3‐aminoquinoline. Reaction of 12b in ethyl acetate with tritium gas in presence of a 5% platinum on carbon catalyst afforded a mixture of ( R )‐5‐(di[2,3‐ 3 H 2 ]propylamino)‐5,6‐dihydro‐4 H ‐imidazo[4,5,1‐ ij ]‐quinolin‐2(1 H )‐one ([ 3 H]U‐86170, 13 , 69 Ci/mmol) and ( R )‐5‐([2,3‐ 3 H 2 ]‐propyl‐amino)‐5,6‐dihydro‐4 H ‐imidazo‐[4,5,1‐ ij ]quinolin‐2(1 H )‐one ([ 3 H]U‐91356, 14 , 34 Ci/mmol) which was separated by preparative reverse‐phase chromatography. U‐86170 and U‐91356 are potent dopamine D2 agonists. The labelled compounds are useful for drug disposition studies. [ 3 H]U‐86170 is also useful as a dopamine D2 agonist radioligand for receptor binding studies.