azd4635

Base Information

• Chemical Name: azd4635
• CAS No.: 1321514-06-0
• Molecular Formula: C₁₅H₁₁ClFN₅
• Molecular Weight: 315.737
• Mol file: 1321514-06-0.mol

Synonyms:6-(2-chloro-6-methylpyridin-4-yl)-5-(4-fluorophenyl)-1,2,4-triazin-3-amine

Chemical Property of azd4635

Chemical Property:

• Boiling Point: 491.5±55.0 °C(Predicted)
• PKA: 1.75±0.63(Predicted)
• Density: 1.387±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

AZD4635 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of azd4635

There total 12 articles about azd4635 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.5%

2-chloro-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (697739-22-3) + 6-bromo-5-(4-fluorophenyl)-1,2,4-triazin-3-amine (1321517-59-2) → 6-(2-chloro-6-methylpyridin-4-yl)-5-(4-fluorophenyl)-1,2,4-triazin-3-amine (1321514-06-0)

Guidance literature:

With (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine; palladium diacetate; potassium carbonate; In tetrahydrofuran; water; at 62 - 66 ℃; Inert atmosphere; Large scale;

DOI:10.1021/acs.oprd.8b00342

Reference yield:

2-chloro-4,6-dimethyl-pyridine (30838-93-8) → 6-(2-chloro-6-methylpyridin-4-yl)-5-(4-fluorophenyl)-1,2,4-triazin-3-amine (1321514-06-0) + C15H11ClFN5

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

1.2: 15 h / 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 24 h / Inert atmosphere

3.1: zinc trifluoromethanesulfonate / isopropyl alcohol / 24 h / 50 °C

With zinc trifluoromethanesulfonate; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; isopropyl alcohol;

DOI:10.1021/acs.oprd.9b00171

Reference yield:

4-fluorobenzoic acid ethyl ester (451-46-7) → 6-(2-chloro-6-methylpyridin-4-yl)-5-(4-fluorophenyl)-1,2,4-triazin-3-amine (1321514-06-0) + C15H11ClFN5

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

1.2: 15 h / 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 24 h / Inert atmosphere

3.1: zinc trifluoromethanesulfonate / isopropyl alcohol / 24 h / 50 °C

With zinc trifluoromethanesulfonate; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; isopropyl alcohol;

DOI:10.1021/acs.oprd.9b00171

upstream raw materials:

2-chloro-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

6-bromo-5-(4-fluorophenyl)-1,2,4-triazin-3-amine

5-(4-fluorophenyl)-1,2,4-triazin-3-amine

1-(4-fluorophenyl)-2,2-dihydroxyethan-1-one

Refernces

• 1、 Douglas, James J.,Adams, Bradley W. V.,Benson, Helen,Broberg, Karl,Gillespie, Paul M.,Hoult, Oliver,Ibraheem, Ameer K.,Janbon, Sophie,Janin, Guillaume,Parsons, Chris D.,Sigerson, Ralph C.,Klauber, David J.. "Multikilogram-Scale Preparation of AZD4635 via C-H Borylation and Bromination: The Corrosion of Tantalum by a Bromine/Methanol Mixture". supporting information. p. 62 - 68. Retrieved 2019/01/15.