2-{[4-(3-Methoxypropoxy)-3-methylpyridine-2-yl]methylthio}-1H-benzimidazole Chemical Properties

Melting point:

120.5-121.50C

Boiling point:

546.4±60.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

10.60±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C18H21N3O2S/c1-13-16(19-9-8-17(13)23-11-5-10-22-2)12-24-18-20-14-6-3-4-7-15(14)21-18/h3-4,6-9H,5,10-12H2,1-2H3,(H,20,21)

InChIKey

BSXAHDOWMOSVAP-UHFFFAOYSA-N

SMILES

C1(SCC2=NC=CC(OCCCOC)=C2C)NC2=CC=CC=C2N=1

CAS DataBase Reference

117977-21-6(CAS DataBase Reference)

Safety Information

HS Code 

2933998350

2-{[4-(3-Methoxypropoxy)-3-methylpyridine-2-yl]methylthio}-1H-benzimidazole Usage And Synthesis

Chemical Properties

Off-White Crystalline Powder

Uses

Rabeprazole Sulfide (Rabeprazole EP Impurity B) is a metabolite of Rabeprazole (R070500).

Synthesis

General procedure for the synthesis of 2-[[[4-(3-methoxypropoxy)-3-methylpyrimidin-2-yl]methyl]thio]-1H-benzimidazole from 2-hydroxymethyl-4-(3-methoxypropoxy)-3-methylpyridine and 1H-benzo[d]imidazole-2-thiol: 100 g of 2-hydroxymethyl-4-(3-methoxypropoxy)-3-methylpyridine ( 473.35 mmol) in a 2L three-necked flask, 1 L of tetrahydrofuran was added as solvent, followed by 71.10 g of 1H-benzo[d]imidazole-2-thiol (473.35 mmol) and 136.58 g of triphenylphosphine (520.69 mmol). Stirring was turned on and the reaction temperature was controlled at 0 °C. Slowly 90.678 g of diethyl azodicarboxylate (520.69 mmol) was added dropwise. After the dropwise addition, the reaction was maintained for 5h to 10h, during which the reaction progress was monitored by TLC. Upon completion of the reaction, the tetrahydrofuran was evaporated to dryness by rotary evaporator, and the resulting crude product was purified by recrystallization from methanol to give 130.0 g of the target product 2-[[[4-(3-methoxypropoxy)-3-methylpyrimidin-2-yl]methyl]thio]-1H-benzimidazole in 80% yield.

References

[1] Patent: CN106674198, 2017, A. Location in patent: Paragraph 0020-0021

2-{[4-(3-Methoxypropoxy)-3-methylpyridine-2-yl]methylthio}-1H-benzimidazole(117977-21-6)Related Product Information

• 1-[[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methyl]-2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole
• RaBeprazole Impurity H
• (S)-Rabeprazole Sodium Salt
• N-[[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methyl] Rabeprazole Sulfone
• 1H-BENZIMIDAZOLE-2-SULFONIC ACID
• 4-Desmethoxypropoxyl-4-chloro Rabeprazole Sulfone
• 4-Desmethoxypropoxyl-4-chloro Rabeprazole
• 4-Nitro-2,3-lutidine-N-oxide
• Rabeprazole IMpurity G
• Rebeprazole sodium
• Rabeprazole
• 4-[(1H-Benzimidazol-2-yl)oxy]-3-methyl-2-pyridinecarboxylic Acid Discontinued See: B203960
• Rabeprazole Impurity 2
• 2-[(4-Chloro-3-Methyl-2-Pyridinyl-methyl)thio]-1H-Benzimidazole
• Rabeprazole Impurity 2
• Rabeprazole Related CoMpound A
• Rabeprazole Impurity 8
• RABEPRAZOLE N-OXIDE