AZD7545

Base Information

• Chemical Name: AZD7545
• CAS No.: 252017-04-2
• Molecular Formula: C19H18ClF3N2O5S
• Molecular Weight: 478.877
• Mol file: 252017-04-2.mol

Synonyms:CS-1842;AZD7545;AZD4575;AZD-7547;AZD 7547;AZD7547;AZD7545/AZD-7545;(R)-4-(3-chloro-4-(3,3,3-trifluoro-2-hydroxy-2-methylpropanamido)phenylsulfonyl)-N,N-dimethylbenzamide;AZD7545,(R)-4-(3-chloro-4-(3,3,3-trifluoro-2-hydroxy-2-methylpropanamido)phenylsulfonyl)-N,N-dimethylbenzamide;(2,4-Dihydroxy-5-isopropylphenyl)5-[(4-methyl-1-piperazinyl)meth yl]-1,3-dihydro-2H-isoindol-2-ylmethanone, 99%;4-[[3-Chloro-4-[[(2R)-3,3,3-trifluoro-2-hydroxy-2-methyl-1-oxopropyl]amino]phenyl]sulfonyl]-N,N-dimethylbenzamide

Chemical Property of AZD7545

Chemical Property:

• Boiling Point: 683.1±55.0 °C(Predicted)
• PKA: 10.39±0.29(Predicted)
• PSA: 67.25000
• Density: 1.473±0.06 g/cm3(Predicted)
• LogP: 2.93830
• Storage Temp.: 2-8°C
• Solubility.: ≥21.85 mg/mL in DMSO; insoluble in H2O; ≥15.63 mg/mL in EtOH with ultrasonic

Purity/Quality:

99% ^*data from raw suppliers

Pyruvate Dehydrogenase Kinase Inhibitor, AZD7545 - CAS 252017-04-2 - Calbiochem ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: AZD 7545 is an inhibitor of pyruvate dehydrogenase (PDH) kinases (PDKs), resulting in an increase in PDH activity with an EC50 value of 5.2 nM for PDK2. It less potently inhibits PDK1 and PDK3 (IC50s = 87 and 600 nM, respectively). AZD 7545 stimulates pyruvate oxidation in rat hepatocytes (EC50 = 105 nM) and significantly elevates muscle PDH activity in obese Zucker rats. It elevates postprandial glucose levels and improves the 24 hour glucose profile in obese, insulin-resistant rats, compared with lean counterparts.

Technology Process of AZD7545

There total 14 articles about AZD7545 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:

oxalyl dichloride (79-37-8) + (R)-N-[2-chloro-4-(4-carboxyphenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (252016-13-0) → AZD7545 (252017-04-2)

Guidance literature:

With dimethyl amine; In methanol; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; N,N-dimethyl-formamide;

Reference yield:

o-chloroaniline (95-51-2) → AZD7545 (252017-04-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: bromine / methanol; acetonitrile / 0 - 5 °C / Large scale reaction

2.1: sodium sulfide / N,N-dimethyl-formamide / 0.5 h / 60 °C

2.2: 3 h / 60 °C

2.3: 60 °C

3.1: sodium hydroxide / ethanol / 80 °C / Large scale reaction

3.2: Large scale reaction

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; acetonitrile / 1.5 h / 20 °C

5.1: thionyl chloride; triethylamine / acetonitrile / 3 h / 20 - 22 °C

5.2: 16 h / 20 °C

6.1: formic acid; dihydrogen peroxide / 60 °C

With sodium sulfide; formic acid; thionyl chloride; dihydrogen peroxide; bromine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In methanol; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/op2003419

Reference yield:

4-amino-3-chlorophenyl thiocyanate (3226-47-9) → AZD7545 (252017-04-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane

2.1: sodiumsulfide nonahydrate / water

2.2: 150 °C

3.1: acetic acid; dihydrogen peroxide / 3 h / 90 °C

With sodiumsulfide nonahydrate; dihydrogen peroxide; acetic acid; triethylamine; In dichloromethane; water;

DOI:10.1021/op800033c

upstream raw materials:

oxalyl dichloride

(R)-N-[2-chloro-4-(4-carboxyphenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

C₁₃H₁₀ClNO₂S

C₁₅H₁₅ClN₂OS