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

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

HS Code 

2933399090

5-Difluoromethoxy-2-{[(3,4-dimethoxy-2-pyridinyl)methyl]thio}-1H-benzimidazole Usage And Synthesis

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

[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(102625-64-9)Related Product Information

• 4-Methoxybenzyl alcohol
• 4-Methoxybenzyl cyanide
• p-Anisaldehyde
• Tribenuron methyl
• p-Anisidine
• 4-Methoxybenzoic acid
• METSULFURON METHYL
• 4-Methoxyphenol
• Anisole
• PANTOPRAZOLE SULPHONE SODIUM SALT
• Methyl acetate
• (Trifluoromethoxy)benzene
• Kresoxim-methyl
• Guaiacol
• Methyl salicylate
• Dimethoxymethane
• Thiophanate-methyl
• 5-(Difluoromethoxy)-2-mercapto-1H-benzimidazole