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
- Molecular Weight:
- 370.25
- MDL Number:
- MFCD32644303
- MOL File:
- Mol file
| Boiling point | 653.0±65.0 °C(Predicted) |
|---|---|
| pka | 1.80±0.10(Predicted) |
| FDA UNII | 3JIJ299EWH |
2-(2,4-DIFLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPYL DIHYDROGEN PHOSPHATE Chemical Properties,Uses,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
2-(2,4-DIFLUOROPHENYL)-1,3-BIS(1H-1,2,4-TRIAZOL-1-YL)PROPYL DIHYDROGEN PHOSPHATE Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Standardpharm Co. Ltd. | 86-714-3992388 | overseasales1@yongstandards.com | United States | 14332 | 58 |
| China National Standard Pharmaceutical Corporation Limited | +8615391658522 | overseasales@yongstandards.com | China | 11922 | 58 |
| Amadis Chemical Company Limited | 571-89925085 | sales@amadischem.com | China | 131957 | 58 |
| Shenzhen Polymeri Biochemical Technology Co., Ltd. | +86-400-002-6226 +86-13028896684; | sales@rrkchem.com | China | 57421 | 58 |
| Guangzhou Dreampharm Biotechnology Co., Ltd. | 020-36607679 17825480238 | 3008233717@qq.com | China | 9919 | 12 |
| Jinan blalong chemical co. LTD | 2710913286@.com | 1513643261@qq.com | China | 14246 | 58 |
| Hubei Xinyang Medical Technology Co., Ltd | 15347293736 15347293736 | 2853117764@qq.com | China | 8329 | 58 |
| Shanghai Sunway Pharmaceutical Technology Co.,Ltd. | 021-51816796-820 13611835272 | sales2@sunwaypharm.com | China | 44458 | 58 |
| Scinova Biotech(Guangzhou) Co., Ltd. | 13268215580 | scinova_sales@163.com | China | 7023 | 58 |
| Hubei De'ao Chemical Research Pharmaceutical Technology Co., Ltd | 18502726233; 18502726233 | 3641133981@qq.com | China | 9706 | 58 |