biostudies-literatureUnknown5(27)Lienard PThe process selection and subsequent development of a reliable, scalable synthesis of the anticancer prodrug tirapazamine (SR259075) is described in this paper. Reaction of benzofuroxan with cyanamide in acetonitrile in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene at 20-25 °C afforded, after an acidic workup, the targeted molecule in good yield at a kilogram scale. Notable critical parameters and safety enhancements are defined and successfully implemented to produce three consecutive validation batches in a reproducible manner.ACS omega16556-16561https://www.ebi.ac.uk/biostudies/studies/S-EPMC7364547biostudies-literatureDevelopment and Validation of a Kilogram-Scale Synthesis of Tirapazamine.PMC7364547Elenbaas SLienard PfalseDevelopment and Validation of a Kilogram-Scale Synthesis of Tirapazamine.The process selection and subsequent development of a reliable, scalable synthesis of the anticancer prodrug tirapazamine (SR259075) is described in this paper. Reaction of benzofuroxan with cyanamide in acetonitrile in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene at 20-25 °C afforded, after an acidic workup, the targeted molecule in good yield at a kilogram scale. Notable critical parameters and safety enhancements are defined and successfully implemented to produce three consecutive validation batches in a reproducible manner.2020-01-01T00:00:00Z2020 Jul2025-04-21T17:00:06.895Z2025-04-21T17:00:06.895ZS-EPMC73645473268582010.1021/acsomega.0c01250