Organic Synthesis | Rapid Three-step Synthesis of a Channel Blocker
Pyrazole-based ion-channel inhibitors are highly selective drugs with potential to cure various diseases. Employing high-temperature reaction conditions in sealed vials the multistep synthesis can be significantly enhanced resulting in short time reaction steps.
The reaction sequence to the potential channel inhibitor involves common standard chemical transformation procedures. This makes it a beneficial example for teaching modern synthesis techniques.
In the first step a pyrazole is formed by simple condensation of a phenyl hydrazine with a β-dicarbonyl compound. In the second step the nitro-group is reduced by a simple palladium-catalyzed transfer hydrogenation. The final amidation is performed by reacting the intermediate amine with a proper carboxylic acid.
Having a chlorine group present in the target compound imposed a beneficial pharmacological activity.
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