6-BROMO-[1,2,4]TRIAZOLO[1,5-A]PYRIDINE Chemical Properties

Melting point:

100-102

Density 

1.89±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Solid

pka

1.46±0.30(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C6H4BrN3/c7-5-1-2-6-8-4-9-10(6)3-5/h1-4H

InChIKey

CXRXKDSDRWLKTK-UHFFFAOYSA-N

SMILES

C12=NC=NN1C=C(Br)C=C2

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-24/25

WGK Germany 

3

Hazard Note 

Harmful/Irritant/Keep Cold

HS Code 

29349990

6-BROMO-[1,2,4]TRIAZOLO[1,5-A]PYRIDINE Usage And Synthesis

Chemical Properties

Off-white powder

Uses

A selective inhibitor of ALK5 kinase

Synthesis

General procedure: N'-(5-bromo-2-pyridinyl)-N,N-dimethylformamidine (4 g, 17.54 mmol, 1.00 eq.) was dissolved in methanol (40 mL) under nitrogen protection and cooled to 0 °C. Subsequently, pyridine (4 mL, 2.00 eq.) and aminoxysulfonic acid (3.6 g, 31.83 mmol, 1.30 eq.) were added sequentially. The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was diluted with ethyl acetate (150 mL) and washed sequentially with saturated aqueous sodium carbonate solution (50 mL x 1) and water (50 mL x 2). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent of ethyl acetate/hexane (1:1) to afford 6-bromo-[1,2,4]triazolo[1,5-A]pyridine 2.5 g (72% yield) as a solid. LC/MS (Method D, ESI): retention time = 1.1 min, m/z = 198.0 [M+H]+.

References

[1] Patent: WO2013/127266, 2013, A1. Location in patent: Page/Page column 141
[2] Patent: WO2013/127267, 2013, A1. Location in patent: Page/Page column 92
[3] Patent: WO2013/127268, 2013, A1. Location in patent: Page/Page column 67
[4] Patent: WO2013/130935, 2013, A1. Location in patent: Paragraph 0206
[5] Patent: WO2013/130943, 2013, A1. Location in patent: Paragraph 0214

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