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

Base Information

• Chemical Name: 2-[[(4-Methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
• CAS No.: 73590-60-0
• Molecular Formula: C16H17N3O2S
• Molecular Weight: 315.396
• DSSTox Substance ID: DTXSID101148345
• Nikkaji Number: J379.046K
• ChEMBL ID: CHEMBL10184
• Mol file: 73590-60-0.mol

Synonyms:73590-60-0;CHEMBL10184;2-[[(4-Methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole;2-(4-Methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfinyl)-1H-benzoimidazole;2-[[(4-Methoxy-3,5-dimethylpyridin-2-yl)-methyl]sulphinyl]-1H-benzimidazole;SCHEMBL5348112;JDVPIZHFGBVEBT-UHFFFAOYSA-N;DTXSID101148345;BDBM50009026;2-[(3,5-Dimethyl-4-methoxy-2-pyridinyl)methylsulfinyl]-1H-benzimidazole;2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole;2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulphinyl]benzimidazole;2-[[(4-Methoxy-3,5-Dimethylpyridin-2-yl)methyl]sulphinyl]-1H-Benzimidazole

Chemical Property of 2-[[(4-Methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

Chemical Property:

• Boiling Point: 573.6±60.0 °C(Predicted)
• PKA: 9.58±0.10(Predicted)
• PSA: 87.08000
• Density: 1.37±0.1 g/cm3(Predicted)
• LogP: 3.75680
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 315.10414797
• Heavy Atom Count: 22
• Complexity: 409

Purity/Quality:

>95% ^*data from raw suppliers

4''-DesmethoxyOmeprazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=CC=CC=C3N2
• Uses: 4''-Desmethoxy Omeprazole is one of two impurities in the synthesis of Esomeprazole, an anti-ulcerative drug for treatment of acid-related diseases.

Technology Process of 2-[[(4-Methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

There total 5 articles about 2-[[(4-Methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole 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: 75.0%

→ 2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole (73590-60-0)

Guidance literature:

Reference yield: 66.8%

2-[(3,5-dimethyl-4-methoxy-2-pyridinylmethyl)thio]-1H-benzimidazole (73590-87-1) → 2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole (73590-60-0)

Guidance literature:

With sodium hypochlorite; sodium hydroxide; In water; ethyl acetate; at 20 ℃;

DOI:10.1016/j.ejmech.2019.112027

Reference yield:

(4-methoxy-3,5-dimethylpyridin-2-yl)methanol (86604-78-6) → 2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole (73590-60-0)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / dichloromethane / 2 h / 20 °C

2: sodium hydroxide / methanol / 0.5 h / 20 °C

3: sodium hydroxide; sodium hypochlorite / ethyl acetate; water / 20 °C

With sodium hypochlorite; thionyl chloride; sodium hydroxide; In methanol; dichloromethane; water; ethyl acetate;

DOI:10.1016/j.ejmech.2019.112027

upstream raw materials:

2-[(3,5-dimethyl-4-methoxy-2-pyridinylmethyl)thio]-1H-benzimidazole

(4-methoxy-3,5-dimethylpyridin-2-yl)methanol

(chloromethyl)-4-methoxy-3,5-dimethylpyridine

Benzimidazol-2-thiol

Downstream raw materials:

acetic acid

Refernces

• 1、 Arreguin-Espinosa, Roberto,Calderón-Jaimes, Ernesto,Cuevas-Cruz, Miguel,Gómez-Manzo, Saúl,Hernández-Ochoa, Beatriz,Méndez-Tenorio, Alfonso,Marcial-Quino, Jaime,Ramírez-Nava, Edson Jiovany,Rocha-Ramírez, Luz María,Sánchez-Carrillo, Adrián,Santos-Segura, Araceli. "Enhanced Antigiardial Effect of Omeprazole Analog Benzimidazole Compounds". . . Retrieved 2020/09/18.
• 2、 -. "N-substituted derivatives of 2-(pyridylalkenesulfinyl) benzimidazoles as gastric antisecretory agents". . . Retrieved 2008/06/13.