Synthesis of 13C- and 14C-labeled 1192U90, an ortho-amino benzamide with a preclinical atypical antipsychotic profile
✍ Scribed by Mark H. Norman; Stephen D. Gabriel
- Publisher
- John Wiley and Sons
- Year
- 1996
- Tongue
- French
- Weight
- 571 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Three isotopic forms of potential antipsychotic agent 1192U90 (2-amino-N-(4-(4-( 1.2benzisothiazol-3-y1)-1-piperaziny1)butyl)benzamide) were synthesized: one containing 13C-isotopes and two containing l4C-isotopes. The compound in which the ortho-amino benzamide ring is completely %XabeIed was prepared in a four-step sequence starting from [ 13C61aniline. The 14C-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)-l-piperazinyl)-l,2-benzisothiazole with isatoic anhydride. The first 14C-labeled compound (3) was prepared from 14C-labeIed 3-(4-(4-aminobutyl)-l-piperazinyl)-1,2benzisothiazole, while the second compound (4) derived its isotopic label from [ 14C]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%.