Synthesis of 3H- and 2H4-labelled versions of the hypoxia-activated pre-prodrug 2-((2-bromoethyl)-2,4-dinitro-6-(((2-(phosphonooxy)ethyl)amino)carbonyl)anilino)ethyl methanesulfonate (PR-104)

H-3- and H-2(4)-versions of the hypoxia-activated pre-prodrug PR-104 [2-[(2-bromoethyl)-2,4-dinitro-6-[[[2(phosphonooxy)ethyl]amino]carbonyl]anilino]ethyl methanesulfonate], labelled in the ethylcarboxamide side chain, have been prepared, respectively, by [H-3]NaBH4 reduction of a precursor late stage aldehyde, and by late stage incorporation of deuterium with 2-amino[1,1,2,2-H-2(4)]ethanol. Copyright (c), 2007 John Wiley & Sons, Ltd.