3-CHLORO-5-METHOXYPYRIDAZINE Chemical Properties

Boiling point:

285 ºC

Density 

1.292

Flash point:

126 ºC

storage temp. 

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

pka

2.45±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C5H5ClN2O/c1-9-4-2-5(6)8-7-3-4/h2-3H,1H3

InChIKey

XLGRINRFBNCHQS-UHFFFAOYSA-N

SMILES

C1(Cl)=NN=CC(OC)=C1

Safety Information

HS Code 

2933998090

3-CHLORO-5-METHOXYPYRIDAZINE Usage And Synthesis

Uses

3-Chloro-5-methoxypyridazine is used to synthesize potent and selective inhibitors of glycogen synthase kinase 3 with good cellular efficacy.

Synthesis

5-Methoxypyridazin-3(2H)-one (250 mg, 1.98 mmol) was used as starting material and suspended in phosphoryl chloride (1.5 mL, 16 mmol). The reaction mixture was stirred at 100 °C for 10 min. After completion of the reaction, the mixture was slowly poured into ice water and the pH was adjusted to alkaline by adding sodium carbonate. Subsequently, the mixture was extracted with ether and the organic phases were combined and dried with anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure. The resulting residue was recrystallized with 1,2-dichloroethane to give 130 mg of 3-chloro-5-methoxypyridazine in 45% yield. The product was analyzed by LC-MS (Method 5): r = 0.85 mm; MS (ESIpos): m/z = 145 [M + H]+. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 2.495 (0.78), 2.499 (1.07), 2.503 (0.84), 3.317 (11.94). 3.944 (16.00), 7.528 (2.28), 7.534 (2.29), 8.988 (2.34), 8.994 (2.34).

References

[1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 5, p. 1473 - 1476
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 19, p. 4716 - 4730
[3] Monatshefte fuer Chemie, 1989, vol. 120, p. 329 - 342
[4] Patent: WO2017/102091, 2017, A1. Location in patent: Page/Page column 455; 456

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