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• Synthesis

  The synthesis steps of Tecovirimat are as follows: A mixture of cycloheptatriene (5 g, 54.26 mmol) and maleic anhydride (6.13 g, 62.40 mmol) was placed in 35 mL of xylene, and the reaction mixture was heated under argon protection and refluxed overnight. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered to collect the brownish-yellow precipitate, and dried to give 2.94 g (28%) of the target product, which is a mixture of intermediates I and II (compound I usually dominates in this mixture, at least 80% by weight. If necessary, the purity of compound I can be further improved by recrystallization. The weight of the isomer of compound I, compound II, is generally less than 20% and varies with reaction conditions). The mother liquor was concentrated to dryness, and the residue was separated by column chromatography to obtain pure compound II, which can be further purified by recrystallization if necessary.
  

  The intermediate compound I (150 mg, 0.788 mmol) prepared in the previous step and 4-trifluoromethylbenzoylhydrazine (169 mg, 0.827 mmol) were mixed in ethanol (10 mL), and then transferred to acetone and heated overnight. After the reaction was complete, the solvent was removed from the resulting reaction mixture by rotary evaporation under vacuum. Purification by silica gel column chromatography with 1/1 n-hexane/ethyl acetate yielded 152 mg (51%) of the product Tecovirimat.
  

  

  Figure: Synthetic Route of Tecovirimat

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