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Synthesis of 13 C‐ and 14 C‐labeled 1192U90, an ortho ‐amino benzamide with a preclinical atypical antipsychotic profile
Author(s) -
Norman Mark H.,
Gabriel Stephen D.
Publication year - 1996
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/(sici)1099-1344(199603)38:3<269::aid-jlcr838>3.0.co;2-l
Subject(s) - chemistry , benzamide , aniline , carbon 14 , yield (engineering) , specific activity , radiochemistry , stereochemistry , organic chemistry , physics , materials science , quantum mechanics , metallurgy , enzyme
Three isotopic forms of potential antipsychotic agent 1192U90 (2‐amino‐N‐(4‐(4‐(1,2‐benzisothiazol‐3‐yl)‐1‐piperazinyl)butyl)benzamide) were synthesized: one containing 13 C‐isotopes and two containing 14 C‐isotopes. The compound in which the ortho ‐amino benzamide ring is completely 13 C‐labeled was prepared in a four‐step sequence starting from [ 13 C 6 ]aniline. The 14 C‐labeled compounds were prepared by methods analogous to those previously described for the unlabeled material. The key step involved the condensation of 3‐(4‐(4‐aminobutyl)‐1‐piperazinyl)‐1,2‐benzisothiazole with isatoic anhydride. The first 14 C‐labeled compound ( 3 ) was prepared from 14 C‐labeled 3‐(4‐(4‐aminobutyl)‐1‐piperazinyl)‐1,2‐benzisothiazole, while the second compound ( 4 ) derived its isotopic label from [ 14 C]isatoic anhydride. Compound 3 had a specific activity of 26.55 mCi/mmol, a radiochemical purity of 99.3%, and a radiochemical yield of 3.4% based on 9 . Compound 4 had a specific activity of 22.67 mCi/mmol and a radiochemical purity of 99.2%.