2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID Chemical Properties

Melting point:

140 °C

Boiling point:

170°C

Density 

1.35±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-0.55±0.41(Predicted)

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36-22

Safety Statements 

26-36/37/39-22

HazardClass 

IRRITANT

HS Code 

29339900

Toxicity

mouse,LD50,intraperitoneal,600mg/kg (600mg/kg),BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLDBEHAVIORAL: IRRITABILITYBEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY),Journal of Medicinal Chemistry. Vol. 12, Pg. 122, 1969.

2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID Usage And Synthesis

Chemical Properties

Pink solid

Synthesis

To a stirred ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate (2.00 g) solution of ethanol/water (1:1, 30 mL) was added lithium hydroxide (4.00 g) and the reaction was stirred for 4 hours at room temperature. Upon completion of the reaction, the reaction mixture was concentrated to half of the original volume, followed by the slow addition of 6N hydrochloric acid at 0 °C and adjusting the pH to 6. The precipitated solid was collected by filtration and dried in a vacuum oven to afford 2-methylimidazo[1,2-a]pyridine-3-carboxylic acid (1.53 g, 88% yield) as an off-white solid.ESI-MS analysis showed the molecular ion peaks as 177 [M + H]+.

References

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7525 - 7545
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 15, p. 4223 - 4232
[3] Farmaco, Edizione Scientifica, 1982, vol. 37, # 1, p. 22 - 35
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 5, p. 1870 - 1873
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5293 - 5305

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