The syntheses of [13 C6 ] and [phenyl-14 C(U)]BMS-816336, an inhibitor of 11ß-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 11ß-hydroxysteroid dehydrogenase type 1 for type 2 diabetes, the synthesis of carbon-14 labeled material was required for use in metabolic profiling. [Phenyl-14 C(U)]BMS-816336 was synthesized in 8 steps and 22% radiochemical yield from commercially available [14 C(U)]bromobenzene. The radiochemical purity of [phenyl-14 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 [13 C6 ]BMS-816336 for use as a liquid chromatography/mass spectrometry standard. [13 C6 ]BMS-816336 was also prepared in 8 labeled steps in 26% yield from [13 C6 ]bromobenzene.