The enantiomerically pure benzodioxane derivative (VIII) was obtained in a straightforward route including five steps starting from pyrocatechin (I). Racemic (VI) was then resolved by means of crystallization with (-)-O,O'-dibenzoyl-L-tartaric acid.
The pyridazinone intermediate (XII) was prepared from dihydroxypyridazine (IX) in three synthetic steps.
Finally, N-alkylation of the potassium salt of (XII) with the base form of (VIII) was performed in dimethyl sulfoxide to afford GYKI-16084.