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- W2029191574 abstract "Methapyrilene, I, once a commonly found antihistamimic drug, has been synthesized with four deuterium labels, three of which are on the thiophene ring. Initially, thiophene was deuterated by solvolysis of the tetramercuric acetate-derivative with deuterium chloride. Carbonylation of the thiophene ring at the 2-position, by the addition of dimethylformamide to the 2-lithio-derivative, gave [3,4,5-d3] thiophene-2-carboxaldehyde. Condensation of this aldehyde with 2-aminopyridine was followed by reduction of the resulting imine with sodium borodeuteride to yield the N-([3,4,5-d3]-2-thienyl[d]-methylene)-2-aminopyridine, VIII. Alkylation of the lithium salt of VIII with dimethylaminoethylchloride gave N, N-dimethyl-N'-[2-pyridyl]-N'-([3,4,5-d3]-2-thienyl-[d]methylene)-1,2-ethane diamine, I, in good yield. Combustion analysis, 500 mHz NMR, and mass spectrometry confirmed the identity of the product which will be useful for metabolic studies." @default.
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- W2029191574 date "1987-12-01" @default.
- W2029191574 modified "2023-09-24" @default.
- W2029191574 title "Synthesis of a deuterium labeled variant of the rat hepatocarcinogen, methapyrilene" @default.
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- W2029191574 doi "https://doi.org/10.1002/jlcr.2580241209" @default.
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