3-Amino-4-bromo-6-chloropyridazine Chemical Properties

Boiling point:

385.4±37.0 °C(Predicted)

Density 

1.960

storage temp. 

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

pka

1.93±0.10(Predicted)

form 

powder

color 

Light brown to brown

InChI

InChI=1S/C4H3BrClN3/c5-2-1-3(6)8-9-4(2)7/h1H,(H2,7,9)

InChIKey

FGOWNGCSUSKHQI-UHFFFAOYSA-N

SMILES

C1(N)=NN=C(Cl)C=C1Br

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN2811

HS Code 

2933998090

3-Amino-4-bromo-6-chloropyridazine Usage And Synthesis

Appearance

Pale-yellow to yellow-brown Solid

Uses

4-Bromo-6-chloropyridazin-3-amine is a compound involved in the preparation of novel potent imidazo[1,2-b]pyridazine PDE10a inhibitors.

Synthesis

Example I (1) Bromine (9.71 g, 3.15 mL, 60.75 mmol) was slowly added dropwise to a mixed solution containing 3-amino-6-chloropyridazine (7.87 g, 60.75 mmol), methanol (115 mL) and sodium bicarbonate (10.22 g, 121.67 mmol). The reaction mixture was stirred at room temperature for 16 hours and then filtered. Water (500 mL) was added to the filtrate and subsequently extracted with ethyl acetate (3 × 500 mL). The organic layers were combined and concentrated under reduced pressure. The resulting residue was purified by fast chromatography using 1:1 hexane/ethyl acetate as eluent, resulting in 5.40 g of 3-amino-4-bromo-6-chloropyridazine in 43% yield.

References

[1] Patent: WO2014/9305, 2014, A1. Location in patent: Page/Page column 29
[2] Patent: US2015/203498, 2015, A1. Location in patent: Paragraph 0155; 0156; 0157
[3] Patent: WO2009/100375, 2009, A1. Location in patent: Page/Page column 44-45
[4] Patent: WO2010/42699, 2010, A1. Location in patent: Page/Page column 114-115
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 23, p. 10414 - 10423

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