4-Desmethoxypropoxyl-4-methoxy Rabeprazole

Base Information

• Chemical Name: 4-Desmethoxypropoxyl-4-methoxy Rabeprazole
• CAS No.: 102804-77-3
• Molecular Formula: C15H14N3O2S
• Molecular Weight: 301.369
• UNII: L6M23VJ488
• DSSTox Substance ID: DTXSID50468595
• Nikkaji Number: J705.701F
• Mol file: 102804-77-3.mol

Synonyms:4-Desmethoxypropoxyl-4-methoxy Rabeprazole;102804-77-3;L6M23VJ488;UNII-L6M23VJ488;2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole;Rabeprazole sodium impurity E [EP];1H-Benzimidazole, 2-(((4-methoxy-3-methyl-2-pyridinyl)methyl)sulfinyl);2-((RS)-((4-Methoxy-3-methylpyridin-2-yl)methyl)sulfinyl)-1H-benzimidazole;2-(((4-Methoxy-3-methylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole;2-[(4-METHOXY-3-METHYLPYRIDIN-2-YL)METHANESULFINYL]-1H-1,3-BENZODIAZOLE;1H-Benzimidazole, 2-[[(4-methoxy-3-methyl-2-pyridinyl)methyl]sulfinyl]-;SCHEMBL23957939;DTXSID50468595;AKOS028109832;CS-0166550;FT-0666068;A1-04635;J-000802;RABEPRAZOLE SODIUM IMPURITY E [EP IMPURITY];2-(((4-Methoxy-3-methylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole (Rabeprazole Impurity

Chemical Property of 4-Desmethoxypropoxyl-4-methoxy Rabeprazole

Chemical Property:

• Melting Point: 141-143°C (dec.)
• Boiling Point: 571.7±60.0 °C(Predicted)
• PKA: 9.58±0.10(Predicted)
• PSA: 87.08000
• Density: 1.40±0.1 g/cm3(Predicted)
• LogP: 3.44840
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 301.08849790
• Heavy Atom Count: 21
• Complexity: 382

Purity/Quality:

NLT 98% ^*data from raw suppliers

4-Desmethoxypropoxyl-4-methoxyRabeprazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3N2)OC
• Uses: A process impurity of Rabeprazole (R070500).

Technology Process of 4-Desmethoxypropoxyl-4-methoxy Rabeprazole

There total 8 articles about 4-Desmethoxypropoxyl-4-methoxy Rabeprazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 57.0%

2-[[(4-methoxy-3-methylpyridin-2-yl)methyl]mercapto]-1H-benzimidazole (102804-82-0) → 2-[(RS)-[(4-methoxy-3-methylpyridin-2-yl)methyl]sulfinyl]-1H-benzimidazole (102804-77-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -15 - -10 ℃; for 1h;

Reference yield:

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + methoxypropanol (1589-49-7) + Benzimidazol-2-thiol (134469-07-1) → 2-[(RS)-[(4-chloro-3-methylpyridin-2-yl)methyl]sulfinyl]-1H-benzimidazole (168167-42-8) + 2-[[(RS)-(1H-benzimidazol-2-yl)sulfinyl]methyl]-4-(3-methoxypropoxy)-3-methylpyridine 1-oxide (924663-38-7) + 2-[(RS)-[(4-methoxy-3-methylpyridin-2-yl)methyl]sulfinyl]-1H-benzimidazole (102804-77-3) + rabeprazole (117976-89-3,177795-59-4)

Guidance literature:

Multistep reaction. Further byproducts given;

Reference yield:

4-chloro-2,3-dimethylpyridine-N-oxide (59886-90-7) → 2-[(RS)-[(4-methoxy-3-methylpyridin-2-yl)methyl]sulfinyl]-1H-benzimidazole (102804-77-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaOH / dimethylsulfoxide / 1 h / 60 °C

1.2: 15 g / dimethylsulfoxide / 4 h / 60 °C

2.1: 5 h / 120 °C

3.1: NaOH / H₂O / 1 h / 25 °C

4.1: 90 percent / SOCl₂ / CH₂Cl₂ / 1 h / 25 °C

5.1: 88 percent / NaOH / H₂O / 3 h / 25 °C

6.1: 57 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / -15 - -10 °C

With sodium hydroxide; thionyl chloride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; dimethyl sulfoxide;

upstream raw materials:

2,3-dimethyl-4-nitropyridine N-oxide

methoxypropanol

Benzimidazol-2-thiol

2-[[(4-methoxy-3-methylpyridin-2-yl)methyl]mercapto]-1H-benzimidazole

Refernces