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Preparation of two D2 partial agonists in C‐14 and stable isotope labeled forms
Author(s) -
Elmore Charles S.,
Powell Mark E.,
Xiong Hui,
Wu Ye,
Wang Lijuan,
Saunders David,
Urbanek Rebecca A.
Publication year - 2012
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.2951
Subject(s) - chemistry , isothiocyanate , yield (engineering) , ring (chemistry) , iodide , methyl iodide , medicinal chemistry , hydrazine (antidepressant) , stable isotope ratio , isotope , stereochemistry , organic chemistry , chromatography , materials science , physics , quantum mechanics , metallurgy
In support of a program to develop a treatment for diseases resulting from an imbalance in dopamine levels, two drug candidates, 1 and 2, were prepared in stable isotope and C‐14 labeled forms. Both compounds contained an aminothiazole ring, and the C‐14 label was introduced into the ring using KS 14 CN. However, the use of KS 14 CN to form [ 14 C]‐2 gave poor results; therefore, benzoyl [ 14 C]isothiocyanate was used instead, which led to a much improved yield. The stable isotope labeled forms were prepared with the label in the side chain from [ 2 H 5 ]ethyl iodide for [ 2 H 5 ]‐1 and from 1‐[ 13 C]methyl [ 15 N 2 ]pyrazole[ 13 C]carboxaldehyde, which was prepared in turn from [carbonyl‐ 13 C]DMF, [ 15 N 2 ]hydrazine sulfate, and [ 13 C]methyliodide for [ 13 C 2 , 15 N 2 ]‐2. Copyright © 2012 John Wiley & Sons, Ltd.