azd4635 Chemical Properties

Boiling point:

491.5±55.0 °C(Predicted)

Density 

1.387±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMSO:56.65(Max Conc. mg/mL);179.42(Max Conc. mM)
DMSO:PBS(pH 7.2) (1:3):0.25(Max Conc. mg/mL);0.79(Max Conc. mM)
DMF:30.0(Max Conc. mg/mL);95.01(Max Conc. mM)

form 

A crystalline solid

pka

1.75±0.63(Predicted)

color 

Off-white to yellow

InChI

InChI=1S/C15H11ClFN5/c1-8-6-10(7-12(16)19-8)14-13(20-15(18)22-21-14)9-2-4-11(17)5-3-9/h2-7H,1H3,(H2,18,20,22)

InChIKey

NCWQLHHDGDXIJN-UHFFFAOYSA-N

SMILES

N1C(C2C=C(C)N=C(Cl)C=2)=C(C2=CC=C(F)C=C2)N=C(N)N=1

azd4635 Usage And Synthesis

Uses

AZD4635, is a novel adenosine 2A receptor (A2AR) inhibitor with a Ki of 1.7 nM.

Synthesis

6-Bromo-5-(4-fluorophenyl)-1,2,4-triazin-3-amine (1 mole-equivalent), 2-chloro-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1 mole-equivalent), and K2CO3 (1.5 mole-equivalent) were used as raw materials suspended in a solvent mixture of 1,4-dioxane and water (v/v ratio 2 :1; 10 mL solvent/g 6-bromo-5-(4-fluorophenyl)-1,2,4-triazin-3-amine). The mixture was degassed and dichlorobis[bis(4-dimethylaminophenyl)phosphino]palladium(II) (2 mol%) was added as a catalyst, and the reaction was heated and refluxed until complete consumption of 6-bromo-5-(4-fluorophenyl)-1,2,4-triazin-3-amine was confirmed by LCMS monitoring. Upon completion of the reaction, the reaction mixture was cooled, diluted with water, extracted with dichloromethane and the organic phase was separated by a phase separator. The organic phase was concentrated under reduced pressure and purified by gradient fast chromatography using a mixture of ethyl acetate and hexane solvents as eluent to give the final target product 6-(2-chloro-6-methylpyridin-4-yl)-5-(4-fluorophenyl)-1,2,4-triazin-3-amine in 61% yield.

References

[1] Patent: WO2011/95625, 2011, A1. Location in patent: Page/Page column 177

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