Unii-uzt71BQ5OO

Base Information

• Chemical Name: Unii-uzt71BQ5OO
• CAS No.: 156601-79-5
• Molecular Formula: C₁₈H₁₉N₃O₂S
• Molecular Weight: 341.434
• UNII: UZT71BQ5OO
• Wikidata: Q27291349
• NCI Thesaurus Code: C84002
• Mol file: 156601-79-5.mol

Synonyms:Nepaprazole;Nepaprazole [INN];156601-79-5;UNII-UZT71BQ5OO;UZT71BQ5OO;(9R)-9-[(S)-1H-Benzimidazol-2-ylsulfinyl]-4-methoxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine;(+-)-(9R*)-9-((SS*)-2-Benzimidazolylsulfinyl)-6,7,8,9-tetrahydro-4-methoxy-5H-cyclohepta(b)pyridine;(- )-(9R*)-9-((SS*)-2-Benzimidazolylsulfinyl)-6,7,8,9-tetrahydro-4-methoxy-5H-cyclohepta(b)pyridine.;SCHEMBL636561;Q27291349;(+/-)-(9RS)-9-((SR)-2-BENZIMIDAZOLYLSULFINYL)(-6,7,8,9-TETRAHYDRO-4-METHOXY-5H-CYCLOHEPTA(B)PYRIDINE

Chemical Property of Unii-uzt71BQ5OO

Chemical Property:

• Vapor Pressure: 1.32E-15mmHg at 25°C
• Boiling Point: 626.4°Cat760mmHg
• Flash Point: 332.6°C
• PSA: 87.08000
• Density: 1.39g/cm³
• LogP: 4.40750
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 341.11979803
• Heavy Atom Count: 24
• Complexity: 464

Purity/Quality:

Nepaprazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C2CCCCC(C2=NC=C1)S(=O)C3=NC4=CC=CC=C4N3
• Isomeric SMILES: COC1=C2CCCC[C@H](C2=NC=C1)[S@](=O)C3=NC4=CC=CC=C4N3
• Uses: Nepaprazole is a benzimidazole derivative that was discovered to be more potent than Omeprazole (O635000) in proton pump inhibition and antisecretory activity.

Technology Process of Unii-uzt71BQ5OO

There total 13 articles about Unii-uzt71BQ5OO 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: 68.0%

2-<(4-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridin-9-yl)thio>-1H-benzimidazole (136176-91-5) → 2-<(4-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridin-9-yl)sulfinyl>-1H-benzimidazole (156601-79-5) + 2-<(4-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridin-9-yl)sulfinyl>-1H-benzimidazole (156601-79-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -15 ℃; Yield given. Title compound not separated from byproducts;

DOI:10.1248/cpb.42.718

Reference yield: 68.0%

2-<(4-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridin-9-yl)thio>-1H-benzimidazole (136176-91-5) → 2-<(4-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridin-9-yl)sulfinyl>-1H-benzimidazole (156601-79-5) + 2-<(4-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridin-9-yl)sulfinyl>-1H-benzimidazole (156601-79-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -15 ℃; Yield given. Title compound not separated from byproducts;

DOI:10.1248/cpb.42.718

Reference yield:

6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine N-oxide (41043-09-8) → 2-<(4-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridin-9-yl)sulfinyl>-1H-benzimidazole (156601-79-5)

Guidance literature:

Multi-step reaction with 6 steps

1: fuming HNO₃ / 80 °C

2: NaOH / Ambient temperature

3: 1.) Ac₂O, 2.) aq. NaOH / 1.) 80 deg C, 2.) RT

4: SOCl₂ / CHCl₃ / Ambient temperature

5: NaOH / ethanol; H₂O / Heating

6: 1.) m-CPBA, 2.) NaOMe / 1.) CH₂Cl₂, -15 deg C, 2.) CH₂Cl₂, MeOH, RT

With sodium hydroxide; thionyl chloride; nitric acid; sodium methylate; acetic anhydride; 3-chloro-benzenecarboperoxoic acid; In ethanol; chloroform; water;

DOI:10.1248/cpb.42.718

upstream raw materials:

2-<(4-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridin-9-yl)thio>-1H-benzimidazole

6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine N-oxide

9-hydroxy-4-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridine

9-chloro-4-methoxy-6,7,8,9-tetrahydro-5H-cycloheptapyridine