ETHYL 6-CHLOROIMIDAZO[1,2-B]PYRIDAZINE-2-CARBOXYLATE Chemical Properties

Melting point:

155-158

Density 

1.47±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform, Dichloromethane, Ethyl Acetate, Methanol

form 

Solid

pka

0.17±0.30(Predicted)

color 

Brown

InChI

InChI=1S/C9H8ClN3O2/c1-2-15-9(14)6-5-13-8(11-6)4-3-7(10)12-13/h3-5H,2H2,1H3

InChIKey

AZEPEWATPYRPBM-UHFFFAOYSA-N

SMILES

C12=NC(C(OCC)=O)=CN1N=C(Cl)C=C2

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933998090

ETHYL 6-CHLOROIMIDAZO[1,2-B]PYRIDAZINE-2-CARBOXYLATE Usage And Synthesis

Chemical Properties

Brown Solid

Uses

Anti-inflammatory agent.

Synthesis

To a suspension of 6-chloropyridazin-3-amine (10.00 g, 77 mmol) in ethanol (30 mL) at 0 °C, a solution of ethyl 3-bromo-2-oxopropanoate (20.07 g, 93 mmol) in ethanol (5 mL) was slowly added by pipette. After addition, the ice bath was removed and the reaction mixture was stirred at room temperature for 15 min, followed by warming to 80 °C for 30 min. After 2 hours of reaction, the mixture was cooled to room temperature and the precipitated beige solid was collected by vacuum filtration and washed with cold ethanol. The resulting solid was suspended in saturated aqueous NaHCO3 solution and stirred for 30 minutes. The solid was again collected by vacuum filtration and the filter cake was washed with water, dried over a filter and further dried under vacuum to give ethyl 6-chloroimidazo[1,2-b]pyridazine-2-carboxylate as a brown solid (8.8 g, 39.0 mmol, 51% yield). The product was characterized by NMR (400 MHz, chloroform-d3): δ 8.46 (s, 1H), 8.13 (d, J=9.5 Hz, 1H), 7.23 (d, J=9.5 Hz, 1H), 4.49 (q, J=7.2 Hz, 2H), 1.46 (t, J=7.1 Hz, 3H). the LC retention time was 2.29 min (Analytical HPLC method A). LC/MS showed (M+H)+ peaks of 226/228 (ratio about 3:1).

References

[1] Patent: WO2016/149437, 2016, A1. Location in patent: Page/Page column 58
[2] Journal of Pharmacology and Experimental Therapeutics, 2018, vol. 364, # 2, p. 246 - 257
[3] Patent: WO2016/97347, 2016, A1. Location in patent: Page/Page column 149
[4] Patent: WO2016/97359, 2016, A1. Location in patent: Page/Page column 125
[5] Farmaco, 1997, vol. 52, # 4, p. 213 - 217

ETHYL 6-CHLOROIMIDAZO[1,2-B]PYRIDAZINE-2-CARBOXYLATE(64067-99-8)Related Product Information

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