The syntheses of [ C ] and [phenyl- C(U)]BMS-816336, an inhibitor of 11β-hydroxysteroid dehydrogenase type 1, for type 2 diabetes.

Type 2 diabetes is a significant worldwide health problem. To support the development of BMS-816336 as an inhibitor of 11β-hydroxysteroid dehydrogenase type 1 for type 2 diabetes, the synthesis of carbon-14 labeled material was required for use in metabolic profiling. [Phenyl- C(U)]BMS-816336 was synthesized in 8 steps and 22% radiochemical yield from commercially available [ C(U)]bromobenzene. The radiochemical purity of [phenyl- C(U)]BMS-816336 was 100% having a specific activity of 84.4 μCi/mg or 28.8 mCi/mmol for a total of 8.9 mCi. It was also necessary to synthesize [ C ]BMS-816336 for use as a liquid chromatography/mass spectrometry standard. [ C ]BMS-816336 was also prepared in 8 labeled steps in 26% yield from [ C ]bromobenzene.