Synthesis of (R)-5-(Di[2,3-3H2]propylamino)5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one ([3H]U-86170) and (R)-5-([2,3-3H2]Propylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one ([3H]U-91356)

✍ Scribed by Malcolm W. Moon; Richard S. P. Hsi

• Publisher: John Wiley and Sons
• Year: 1992
• Tongue: French
• Weight: 542 KB
• Volume: 31
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580311112

✦ Synopsis

Abstract

(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.