4-CHLORO-1-H-IMIDAZO[4,5-C]PYRIDINE Chemical Properties

Melting point:

179-181 °C

Boiling point:

455.4±25.0 °C(Predicted)

Density 

1.531±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Slightly, Sonicated), Methanol (Slightly, Sonicated)

form 

Solid

pka

7.93±0.40(Predicted)

color 

Pale Beige to Pale Brown

InChI

InChI=1S/C6H4ClN3/c7-6-5-4(1-2-8-6)9-3-10-5/h1-3H,(H,9,10)

InChIKey

DHJMLXBBZRWBPW-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC2N=CNC1=2

Safety Information

HS Code 

2933399990

4-CHLORO-1-H-IMIDAZO[4,5-C]PYRIDINE Usage And Synthesis

Uses

4-Chloro-1H-imidazo[4,5-c]pyridine is used as a reagent in the synthesis of 3-bromo-3-deazaneplanocin and 3-bromo-3-deazaaristeromycin, compounds which exhibit antiviral activity.

Synthesis

The general procedure for the synthesis of 4-chloroimidazo[4,5-C]pyridine using the compound (CAS: 91184-02-0) as starting material was as follows: compound 3 (255 mg, 1.88 mmol) was dissolved in 10 mL of phosphorus oxytrichloride (POCl3), and the reaction was stirred for 3 hr at 110 °C until the reaction solution became clear. Upon completion of the reaction, the excess phosphorous trichloride was removed under vacuum. Subsequently, ice water was added to the reaction mixture, the pH was adjusted to about 9 by slowly adding ammonia dropwise, and an equal volume of methanol (MeOH) was added. At this point, a precipitate appeared in the reaction mixture and the precipitate was collected by filtration. The filtrate was adsorbed on silica gel and purified by silica gel column chromatography, the eluent being a mixture of ethyl acetate (EA) and 5% methanol (MeOH), resulting in the target product 4 in 83% yield. The results of high-resolution mass spectrometry (HRMS-ESI) analysis were as follows: m/z calculated value (C6H5ClN3 [M+H]+) was 154.0166, and the measured value was 154.0171.

References

[1] European Journal of Medicinal Chemistry, 2018, vol. 148, p. 384 - 396
[2] ChemMedChem, 2013, vol. 8, # 6, p. 985 - 993
[3] Patent: US5057517, 1991, A

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