Synthesis, molecular structure, NMR spectroscopic and computational analysis of a selective adenosine A2A antagonist, ZM 241385

Herein, we describe the synthesis of the adenosine A(2A) antagonist ZM 241385 (9) starting from commercially available 2-furanhydrazide (1) and including a comprehensive structural characterization of all the intermediates and the final product. In addition, extensive NMR analysis, including temperature and concentration-dependent experiments, are reported as well as the first single-crystal structure of the compound ZM 241385 (9) as the trihydrate. Furthermore, an extensive structural comparison of the single-crystal structure with the published protein bound X-ray structures is reported.