2-Mercapto-5-methoxyimidazole[4,5-b]pyridine Chemical Properties

Melting point:

238-241°C

Boiling point:

324.9±52.0 °C(Predicted)

Density 

1.55±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder

pka

7.39±0.40(Predicted)

color 

Off white to beige

CAS DataBase Reference

113713-60-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29333990

2-Mercapto-5-methoxyimidazole[4,5-b]pyridine Usage And Synthesis

Uses

2-Mercapto-5-methoxyimidazolium[4,5-b]pyridine is a pyridine derivative that can be used as a pharmaceutical intermediate.

Chemical Properties

White to gray solid

Synthesis

2-Mercapto-5-methoxyimidazo[4,5-b]pyridine (Compound 9c) was synthesized in five steps, methoxylation, nitration, amination, reduction and cyclization, using 2,6-dichloropyridine as starting material in 45.7% overall yield. The structure of the product was confirmed by 1H NMR, mass spectrometry (MS) and infrared spectroscopy (IR). The procedure was as follows: 6-methoxy-3-nitropyridin-2-amine (0.5 g, 3 mmol) was dissolved in a mixed solvent of methanol (100 mL) and water (2 mL), 10% Pd/C catalyst (0.1 g) was added, and the reaction was carried out in a hydrogenation unit under hydrogen (3 bar) atmosphere with shaking until the pressure was constant. After completion of the reaction, the catalyst was removed by filtration and carbon disulfide (1 mL) and potassium hydroxide (0.225 g) were added to the filtrate and refluxed under heat. The progress of the reaction was monitored by thin layer chromatography (TLC), and after completion of the reaction the solvent was removed by concentration under reduced pressure. The resulting solid was recrystallized from ethanol to afford the target product 2-mercapto-5-methoxyimidazo[4,5-b]pyridine (0.187 g, 1.1 mmol) in 35% yield with a melting point of 223-225 °C. IR (cm-1 ): 3262, 3051. 1H NMR (200 MHz, DMSO-d6) δ (ppm): 12.99 (s, 1H , NH), 12.54 (s, 1H, NH), 7.43-7.47 (d, 1H, J = 8.5 Hz, Harom.), 6.55-6.60 (d, 1H, J = 8.5 Hz, Harom.), 3.83 (s, 3H, CH3).13C NMR (50 MHz, DMSO-d6) δ (ppm): 167.60, 160.12, 143.62, 120.17, 119.65, 103.90, 53.49.

References

[1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 12, p. 3669 - 3677
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 23, p. 10080 - 10100
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 5, p. 1371 - 1375
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6289 - 6304

2-Mercapto-5-methoxyimidazole[4,5-b]pyridine(113713-60-3)Related Product Information

• 2-Ethylhexyl mercaptoacetate
• Ornidazole
• Calcium thioglycolate
• 6-Mercaptopurine
• Sodium thioglycolate
• 2-Pyridinethione
• Mercaptoacetic acid
• POTASSIUM THIOGLYCOLATE
• Methimazole
• Pyridine
• 3-Mercaptopropionic acid
• Tenatoprazole
• 2-Mercaptoethanol
• 5-METHOXY-2-[[(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL]THIO]-1H-IMIDAZO[4,5B]PYRIDINE
• Malathion
• 2-Mercapto-5-methoxyimidazole[4,5-n]pyridine
• 2-Mercapto-5-methoxyimidazole[4,5-b]pyridine
• 5-METHOXY-1H-IMIDAZO[4,5-B]PYRIDINE-2-THIOL