2-(2,4-DIFLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPYL DIHYDROGEN PHOSPHATE
- Product Name
- 2-(2,4-DIFLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPYL DIHYDROGEN PHOSPHATE
- CAS No.
- 1807913-50-3
- Chemical Name
- 2-(2,4-DIFLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPYL DIHYDROGEN PHOSPHATE
- Synonyms
- FOSFLUCONAZOLE;FosflucozoleImpurity4;Fosfluconazole Impurity 4;FLUCONAZOLE DIHYDROGEN PHOSPHATE;2-(2,4-DIFLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPYL DIHYDROGEN PHOSPHATE;2-(2,4-Difluorophenyl)-1,3-di(1h-1,2,4-triazol-1-yl)propan-2-yl hydrogen phosphonate;Phosphonic acid, mono[1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-(1H-1,2,4-triazol-1-ylmethyl)ethyl] ester
- CBNumber
- CB6200893
- Molecular Formula
- C13H13F2N6O3P
- Formula Weight
- 370.25
- MOL File
- Mol file
2-(2,4-DIFLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPYL DIHYDROGEN PHOSPHATE Property
- Boiling point:
- 653.0±65.0 °C(Predicted)
- pka
- 1.80±0.10(Predicted)
2-(2,4-DIFLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPYL DIHYDROGEN PHOSPHATE Chemical Properties,Usage,Production
Description
Fosfluconazole, a phosphate prodrug of fluconazole (96), was recently approved for intravenous use in Japan in October 2003. The drug was developed as a water-soluble prodrug by Pfizer as an enhancement to the injectable infusion formulation of fluconazole (96), a very potent antifungal agent, that could be used intravenously in bolus doses requiring smaller volumes of fluid and sodium.
Synthesis
The disclosed manufacturing route of synthesis utilized fluconazole (96) as a precursor and was prepared in two steps using inexpensive starting materials. Fluconazole was dissolved in dichloromethane with pyridine and was treated sequentially with phosphorus trichloride at ¨C13??C and reacted at 13??C for 2 hr followed by an addition of benzyl alcohol at 14-16??C and reacted for 2 hrs at 10-15??C. The mixture was then cooled to 0??C and 30% hydrogen peroxide was added over three hours, maintaining the temperature below 20??C. After stirring the reaction at 20??C for 1hr, the intermediate 97 was isolated in 66% yield. Hydrogenation of the benzyl phosphate at 60 psi in water with 5% palladium on carbon gave the desired phosphate prodrug, fosfluconazole (XI) in 88% yield.
2-(2,4-DIFLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPYL DIHYDROGEN PHOSPHATE Preparation Products And Raw materials
Raw materials
Preparation Products
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