Journal of labelled compounds and radiopharmaceuticals p. 885 - 890 (1997)
Update date:2022-08-04
Topics:
Markus, Bohdan
Allentoff, Alban J.
Desai, Mahesh
Chaudhuri, Naba K.
Duelfer, Timothy
CGS 16949A (Fadrozole HCI) is an aromatase inhibitor currently used in Japan for the treatment of estrogen-dependent cancer. A 14C-labeled form of this compound was synthesized for metabolism and pharmacokinetic studies. The synthesis pathway includes six steps, which are shown in synthetic Scheme 2. Initially, 4-bromotoluene was reacted with [14C]CuCN to yield 4- tolunitrile-[14C]-cyano. The nitrile was brominated on the α carbon to give an intermediate that was used to N-alkylate a known imidazole analogue. The product was treated with thionyl chloride to convert a 3-hydroxy propyl moiety to its chloro analogue. Treatment with potassium butoxide gave [14C] fadrozole as the free base via ring closure. Hydrogen chloride gas was used to give the desired salt [14C]CGS 16949A. Using this procedure, [14C]CGS 16949A was prepared with 97% radiochemical purity. The overall radiochemical yield for the synthesis was 1% from [14C]KCN.
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