Imidazo[1,2-b]pyridazine Chemical Properties

Melting point:

54℃

Density 

1.29±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in dimethylformamide.

form 

powder to crystal

pka

5.30±0.30(Predicted)

color 

White to Light yellow to Light orange

λmax

222nm(MeOH)(lit.)

InChI

InChI=1S/C6H5N3/c1-2-6-7-4-5-9(6)8-3-1/h1-5H

InChIKey

VTVRXITWWZGKHV-UHFFFAOYSA-N

SMILES

C12=NC=CN1N=CC=C2

CAS DataBase Reference

766-55-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HS Code 

29335990

Imidazo[1,2-b]pyridazine Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

Imidazo[1,2-b]pyridazine is used as an intermediate of cefozopran, building block and in fused ring systems.

Synthesis

General procedure for the synthesis of imidazo[1,2-b]pyridazine from 6-chloroimidazo[1,2-b]pyridazine: to a stirred mixed solution of 6-chloroimidazo[1,2-b]pyridazine (800 mg, 5.21 mmol) in methanol (20 mL) and tetrahydrofuran (20 mL) was sequentially added triethylamine (0.8 mL, 5.74 mmol) and Pd/C ( 100 mg, 0.094 mmol). The reaction mixture was placed under hydrogen atmosphere and stirred for 16 hours. Upon completion of the reaction, the mixture was filtered through diatomaceous earth and the diatomaceous earth bed was washed with methanol. The filtrates were combined and concentrated, and the concentrate was subsequently suspended in water and extracted with ethyl acetate (3 x 20 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated to give imidazo[1,2-b]pyridazine (550 mg, 87% yield) as an off-white solid. The product was analyzed by LCMS [m/z 120 (M + H)]; 1H NMR (300 MHz, DMSO-d6) δ 8.51 (dd, J = 4.53, 1.51 Hz, 1H), 8.29 (d, J = 0.76 Hz, 1H), 8.05-8.19 (m, 1H), 7.79 (d, J = 1.13 Hz, 1H), 7.22 (dd, J = 9.44, 4.53 Hz, 1H).

References

[1] Patent: WO2016/210036, 2016, A1. Location in patent: Page/Page column 106; 107

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