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A practical, multigram synthesis of the 2-(2-(4-alkoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide (DPA) class of high affinity translocator protein (TSPO) ligands |
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| Authors: | Samuel D Banister Shane M WilkinsonRaphy Hanani Aaron J ReynoldsDavid E Hibbs Michael Kassiou |
| Institution: | a Brain and Mind Research Institute, Sydney, NSW 2050, Australia b School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia c Faculty of Pharmacy, The University of Sydney, Sydney, NSW 2006, Australia d Discipline of Medical Radiation Sciences, The University of Sydney, Sydney, NSW 2006, Australia |
| Abstract: | A practical, multigram approach to the 2-(2-(4-alkoxyphenyl)-5,7-dimethylpyrazolo1,5-a]pyrimidin-3-yl)acetamide (DPA) class of ligands targeting the translocator protein (TSPO) is described. This synthetic route offers several improvements over all previously described sequences, including the isolation of intermediates without resort to chromatography. The common precursor to the DPA class of high affinity TSPO ligands, N,N-diethyl-2-(2-(4-hydroxyphenyl)-5,7-dimethylpyrazolo1,5-a]pyrimidin-3-yl)acetamide, was produced in 40% yield over six steps, and was cleanly alkylated to give multigram quantities of several DPA analogues in 90-96% yield after recrystallization. |
| Keywords: | Translocator protein Pyrazolo[1 5-a]pyrimidine DPA-714 |
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