5-Difluoromethoxy-2-{[(3,4-dimethoxy-2-pyridinyl)methyl]thio}-1H-benzimidazole CAS 102625-64-9
5-Difluoromethoxy-2-{[(3,4-dimethoxy-2-pyridinyl)methyl]thio}-1H-benzimidazole Basic information
| Product Name: | 5-Difluoromethoxy-2-{[(3,4-dimethoxy-2-pyridinyl)methyl]thio}-1H-benzimidazole |
| Synonyms: | Pantoprazole Related Compound B (25 mg) (5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole);Pantoprazole Thioether;5-(DifluoroMethoxy)-2-(((3,4-diMethoxypyridin-2-yl)Methyl)thio)-1H-benzo[d]iMidazole;5-(DIFLUOROMETHOXY)-2-[[3,4-DIMETHOXY-2-PYRIDINYL)-METHYL]-THIO]-1H- BENZIMIDAZOLE (PANTOPRAZOLE SULPHIDE COMPOUND);Pantoprazole Thioether, 5-(Difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole;5-(Difluoromethoxy)-2-{[3,4-di;5-Difluoromethoxy-2-{[(3,4-dim;5-(DIFLUOROMETHOXY)-2-{[3,4-DIMETHOXY-2-PYRIDINYL)METHYL]THIO}IH- BENZIMIDAZOLE |
| CAS: | 102625-64-9 |
| MF: | C16H15F2N3O3S |
| MW: | 367.37 |
| EINECS: | 1806241-263-5 |
| Product Categories: | Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Various Metabolites and Impurities;Metabolites;Pantoprazole Sodium;(intermediate of pantoprazole) |
| Mol File: | 102625-64-9.mol |
5-Difluoromethoxy-2-{[(3,4-dimethoxy-2-pyridinyl)methyl]thio}-1H-benzimidazole Chemical Properties
| Melting point | 110-118°C |
| Boiling point | 526.3±60.0 °C(Predicted) |
| density | 1.43±0.1 g/cm3(Predicted) |
| storage temp. | Sealed in dry,2-8°C |
| solubility | DMSO (Slightly), Methanol (Slightly) |
| pka | 8.97±0.10(Predicted) |
| color | Off-White to Light Brown |
| BRN | 5358607 |
| Major Application | pharmaceutical |
| InChI | InChI=1S/C16H15F2N3O3S/c1-22-13-5-6-19-12(14(13)23-2)8-25-16-20-10-4-3-9(24-15(17)18)7-11(10)21-16/h3-7,15H,8H2,1-2H3,(H,20,21) |
| InChIKey | UKILEIRWOYBGEJ-UHFFFAOYSA-N |
| SMILES | C1(SCC2=NC=CC(OC)=C2OC)NC2=CC(OC(F)F)=CC=C2N=1 |
| CAS DataBase Reference | 102625-64-9(CAS DataBase Reference) |
Safety Information
| WGK Germany | WGK 3 |
| HS Code | 2933399090 |
| Storage Class | 11 - Combustible Solids |
| Chemical Properties | Beige Solid |
| Uses | A metabolite of Pantoprazole, an antiulcerative, gastric pump inhibitor |
| Uses | Pantoprazole Sulfide (Pantoprazole EP Impurity B) is a metabolite of Pantoprazole (P183000), an antiulcerative, gastric pump inhibitor. |
| Synthesis | 169905-10-6 97963-62-7 102625-64-9 [Example 1] Preparation of 5-(difluoromethoxy)-2-(((3,4-dimethoxypyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole: 920 mL of isopropanol, 92.1 g of 5-difluoromethoxy-2-mercapto-1H-benzimidazole, and 95.8 g of 2-chloromethyl-3,4-dimethoxypyridine were added to the reactor. Sodium hydroxide solution (prepared by dissolving 20.5 g of sodium hydroxide in 920 mL of pure water) was added slowly and dropwise to the above mixture, followed by stirring the reaction mixture for 2 hours at room temperature. Upon completion of the reaction, 920 mL of pure water was added to the mixture and stirring was continued for 1 hour. The resulting solid product was collected by filtration and dried under vacuum to give 137.4 g of the target compound in 87.8% yield with a melting point of 94 °C. |
| References | [1] Patent: WO2009/75516, 2009, A2. Location in patent: Page/Page column 4 [2] Organic Process Research and Development, 2013, vol. 17, # 10, p. 1272 - 1276 |
5-Difluoromethoxy-2-{[(3,4-dimethoxy-2-pyridinyl)methyl]thio}-1H-benzimidazole Preparation Products And Raw materials
| Raw materials | 2-CHLOROMETHYL-3,4-DIMETHOXY PYRIDINE HYDROCHLORIDE-->5-(Difluoromethoxy)-2-mercapto-1H-benzimidazole-->2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride-->2-Chloromethyl-3,4-dimethoxypyridinium chloride-->Isopropyl alcohol-->Sodium hydroxide |
| Preparation Products | Pantoprazole Sodium |
