| Identification | Back Directory | [Name]
azd4635 | [CAS]
1321514-06-0 | [Synonyms]
azd4635
CPD1545
CS-2744
HTL-1071
AZD-4635; HTL-1071
AZD-4635; AZD 4635; AZD4635; HTL-1071; HTL 1071; HTL1071
6-(2-chloro-6-methylpyridin-4-yl)-5-(4-fluorophenyl)-1,2,4-triazin-3-amine
1,2,4-Triazin-3-amine, 6-(2-chloro-6-methyl-4-pyridinyl)-5-(4-fluorophenyl)- | [Molecular Formula]
C15H11ClFN5 | [MDL Number]
MFCD31618022 | [MOL File]
1321514-06-0.mol | [Molecular Weight]
315.73 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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. | [storage]
Store at -20°C | [References]
[1] Patent: WO2011/95625, 2011, A1. Location in patent: Page/Page column 177 |
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