13C- and 14C-labelling of N-[1-(4-chlorophenyl)-1H-pyrrol-2-yl-methyleneamino] guanidinium acetate

• Published in: Journal of labelled compounds & radiopharmaceuticals Vol. 48; no. 8; pp. 621 - 627
• Main Authors: Almeida, Maria, Johannesson, Petra, Boman, Arne, Lundstedt, Torbjörn
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.07.2005; Wiley
• Subjects: 1-(4-chlorophenyl)-1H-pyrrole-13C4; Biological and medical sciences; Chemistry; Contrast media. Radiopharmaceuticals; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Medical sciences; N-[1-(4-chlorophenyl)-1H-pyrrol-2-yl-13C4-methyleneamino]guanidinium acetate; Organic chemistry; Paal-Knorr reaction; Pharmacology. Drug treatments; Preparations and properties; succinic acid-13C4; Paal-Knorr reaction; Isotope labelling; Radiolabelling; Carbon Isotopes; Paal Knorr reaction; Guanidinium compounds; Pyrrole derivatives; succinic acid-13C4; 1-(4-chlorophenyl)-1H-pyrrole-13C4; N-[1-(4-chlorophenyl)-H-pyrrol-2-yl-13C4-methyleneaminolguanidinium acetate; Succinic acid; Chemical synthesis; Carbon 14; Carbon 13
• ISSN: 0362-4803; 1099-1344
• DOI: 10.1002/jlcr.957

N‐[1‐(4‐chlorophenyl)‐1H‐pyrrol‐2‐yl‐13C4‐methyleneamino]guanidinium acetate has been synthesized by a four‐step procedure. This involved reduction of the Weinreb amide N,N′‐dimethyl‐N,N′‐dimethyloxybutane‐1,4‐diamide‐1,2,3,4‐13C4 by Dibal‐H to give the corresponding unstable dialdehyde which is reacted in situ with 4‐chloroaniline to form 1‐(4‐chlorophenyl)‐1H‐pyrrole‐13C4. This pyrrole analogue underwent a Vilsmeyer acylation with POCl3/DMF followed by final reaction with aminoguanidine bicarbonate to produce the desired labelled compound with 99% atom 13C. By using DMF [α‐14C] a radio‐labelled analogue was synthesized with a specific activity of 60 mCi/mmol. Copyright © 2005 John Wiley & Sons, Ltd.