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ChemicalBook CAS DataBase List Deferiprone
30652-11-0

Deferiprone synthesis

10synthesis methods
Deferiprone is a drug that chelates iron and is used to treat thalassaemia major. In 1994 was first approved for use in treating thalassaemia major in 1994 and had been licensed for use in Europe and Asia for many years while awaiting approval in Canada and the United States. On October 14, 2011, it was approved for use in the US under the FDA?’s accelerated approval program.
Synthetic Routes
  • ROUTE 1

    • 202112077391666935.jpg

    Dobbin, Paul S.; Hider, Robert C.; Hall, Adrian D.; Taylor, Paul D.; Sarpong, Patience; Porter, John B.; Xiao, Gaoyi; van der Helm, Dick. Synthesis, physicochemical properties, and biological evaluation of N-substituted 2-alkyl-3-hydroxy-4(1H)-pyridinones: orally active iron chelators with clinical potential. Journal of Medicinal Chemistry. Volume 36. Issue 17. Pages 2448-58. Journal. (1993).

  • ROUTE 2

    • 202112070063819108.jpg

    Fox, Raymond C.; Taylor, Paul D. Efficient syntheses of N-alkyl-3-hydroxy-2-methyl-4(1H)-pyridinones from carbohydrate precursors. Synthetic Communications. Volume 29. Issue 6. Pages 989-1001. Journal. (1999).

202112077391666935.jpg

Dobbin, Paul S.; Hider, Robert C.; Hall, Adrian D.; Taylor, Paul D.; Sarpong, Patience; Porter, John B.; Xiao, Gaoyi; van der Helm, Dick. Synthesis, physicochemical properties, and biological evaluation of N-substituted 2-alkyl-3-hydroxy-4(1H)-pyridinones: orally active iron chelators with clinical potential. Journal of Medicinal Chemistry. Volume 36. Issue 17. Pages 2448-58. Journal. (1993).

-

Yield:-

Steps:

Multi-step reaction with 3 steps
1: 99 percent / KOH / methanol / Ambient temperature
2: 99 percent / ethanol / 22 h / Ambient temperature
3: 80 percent / H2 / Pd/C / methanol / 2 h

References:

Rumbo, Antonio;Mourino, Antonio;Castedo, Luis;Mascarenas, Jose L. [Journal of Organic Chemistry,1996,vol. 61,# 18,p. 6114 - 6120]

FullText

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