Ufiprazole

Base Information

• Chemical Name: Ufiprazole
• CAS No.: 73590-85-9
• Molecular Formula: C17H19N3O2S
• Molecular Weight: 329.423
• Hs Code.: 29339900
• European Community (EC) Number: 615-997-3
• UNII: 6FFV1V867C
• DSSTox Substance ID: DTXSID7057816
• Nikkaji Number: J326.034H
• Wikidata: Q27264821
• NCI Thesaurus Code: C76913
• ChEMBL ID: CHEMBL892
• Mol file: 73590-85-9.mol

Synonyms:H 168-22;omeprazole sulfide;omeprazole sulphide

Chemical Property of Ufiprazole

Chemical Property:

• Vapor Pressure: 1.03E-11mmHg at 25°C
• Melting Point: 122.0 to 126.0 °C
• Refractive Index: 1.649
• Boiling Point: 539.7 °C at 760 mmHg
• PKA: 9.81±0.10(Predicted)
• Flash Point: 280.2 °C
• PSA: 85.33000
• Density: 1.28 g/cm³
• LogP: 3.88420
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 329.11979803
• Heavy Atom Count: 23
• Complexity: 387

Purity/Quality:

99% ^*data from raw suppliers

Omeprazole Sulfide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(C(=C1OC)C)CSC2=NC3=C(N2)C=C(C=C3)OC
• Description: Omeprazole sulfide is an intermediate used in the production of the gastric proton pump inhibitors, omeprazole and esomeprazole . As a degradation product, it is reported to be a direct-acting inhibitor of cytochrome P450 2C19 in pooled human liver microsomes (IC50 = 9.7 μM).
• Uses: A metabolite of Omeprazole Omeprazole Sulfide (Esomeprazol EP Impurity C(Omeprazole EP Impurity C)) is a metabolite of Omeprazole.

Technology Process of Ufiprazole

There total 30 articles about Ufiprazole 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: 100.0%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → omeprazole sulfide (73590-85-9)

Guidance literature:

With tetrabutylammomium bromide; edetate disodium; sodium hydroxide; In dichloromethane; water; pH=10; pH-value;

Reference yield: 95.1%

2-Mercapto-5-methoxybenzimidazole (37052-78-1) + (chloromethyl)-4-methoxy-3,5-dimethylpyridine (84006-10-0) → omeprazole sulfide (73590-85-9)

Guidance literature:

With potassium iodide; sodium hydroxide; In ethanol; at 15 - 55 ℃; for 0.5h; Inert atmosphere; Large scale;

Reference yield: 95.0%

5-methoxy-1,3-dihydro-2H-benzo[d]imidazole-2-thione (37052-78-1) + 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride (86604-75-3) → omeprazole sulfide (73590-85-9)

Guidance literature:

With sodium carbonate; In methanol; for 1.5h; Reflux;

DOI:10.1515/hc-2015-0101

upstream raw materials:

2-(2-hydroxyethyldisulfanylmethyl)-4-methoxy-1-(5-methoxybenzimidazol-2-yl)-3,5-dimethylpyridinium

omeprazole-2-mercaptoethanol disulfide

2-hydroxyethanethiol

omeprazole

Downstream raw materials:

(S)-6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]-sulfinyl]-1H-benzimidazole

omeprazole

omeprazole

(R)-6-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl)-1H-benzoimidazole