Die synthese von mit ¹⁴C‐isotop markierten aryl‐isothiocyanten

Abstract

I n s t i t u t f G rA r z n e i m i t t e l f o r s c h u n g B u d a p e s t -U n g a r n . R e c e i v e d o n S e p t e m b e r 13, 1972. SUMMARY The t h e r m l decomposition of aryl-thioureos labelled with 14C, yielding t h e labelled aryl-isothiocyanates was investigated.Starting out from 2,6-dichloropheny I-, and 2, B-dimethylphenylisothiocyanate, respectively, the corresponding substituted thiazolidine derivatives labelled with radioactive carbon were synt h e t i z e d . ZUSAEIMENFASSUNG Die thermische Zersetung von Aryl-thioharnstoffe, zwecksDarstellung der mit 14C-Isotop markierten Aryl-isothiocyanate wurde untersucht. Aus 2, bzw. 2,phenyl-isothiocyanate ausgehend wmden s u b s t i t u i e r t e , mit radioaktivem Kohlenstoff markierte Thiazoliclin-Derivate synthet i s i e r t .

Imaging agents for myeloperoxidase

“…A 14 C‐label in the thiocarbonyl position was needed to investigate the binding of 1 and 2 to MPO. Use of [ 14 C]potassium thiocyanate 3 to prepare benzoyl [ 14 C]isothiocyanate 5 provided a good starting point for the preparation of xanthine derivatives with the label in the 2‐position. The syntheses of [2‐ 14 C]xanthine derivatives of 1a and 1b were initiated by coupling the correspondingly substituted 1° amine with 5 to give benzamides 6a and 6b , respectively (Scheme ).…”

“…Pyrrolo[3,2‐ d ]pyrimidin‐4‐one labeled with C‐14 was required also. Compound [ 14 C]‐ 2 (Scheme ) was prepared by reacting benzoyl [ 14 C]isothiocyanate 5 with the amine 13 in acetone at elevated temperature. This was followed by a base catalyzed cyclization to obtain the pyrimidone [ 14 C]‐ 2 .…”

“…Tetrahydrofurfurylamine (110 μL, 1.1 mmol) was added to a solution of benzoyl [ 14 C]isothiocyanate, 5 , (~1.85 GBq, ~0.98 mmol) in acetone (4 mL) at 0 °C. The mixture was heated to reflux for 1 h. Water (1 mL) was added, and the mixture was concentrated to dryness.…”

Preparation of two D2 partial agonists in C‐14 and stable isotope labeled forms

“…After convincing ourselves that direct reaction of KS 14 CN with 5 was not the best option for the preparation of 2 , we prepared benzoyl [ 14 C] isothiocyanate ( 6 ) by reacting potassium [ 14 C] thiocyanate with benzoyl chloride in acetonitrile in nearly quantitative yield (Scheme ) . HPLC anaylsis of the product gave two peaks in varying ratios for the same sample.…”

“…HPLC analysis using method A showed 80% radiochemical purity with a single 20% radiolabeled impurity. This impurity co-eluted on HPLC with (S)-benzyl [2][3][4][5][6][7][8][9][10][11][12][13][14]…”