Didehydro rosiglitazone, (5Z)-

Base Information

• Chemical Name: Didehydro rosiglitazone, (5Z)-
• CAS No.: 160596-25-8
• Molecular Formula: C18H17N3O3S
• Molecular Weight: 355.417
• Hs Code.: 2934100000
• European Community (EC) Number: 602-492-8
• UNII: 7JSD8Q9B3G
• DSSTox Substance ID: DTXSID101128074
• Nikkaji Number: J621.161E,J694.827H
• Wikidata: Q27268428
• ChEMBL ID: CHEMBL297312
• Mol file: 160596-25-8.mol

Synonyms:Didehydro rosiglitazone, (5Z)-;160596-25-8;UNII-7JSD8Q9B3G;7JSD8Q9B3G;CHEMBL297312;(5Z)-5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione;122320-74-5;2,4-Thiazolidinedione, 5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methylene)-, (5Z)-;(5Z)-5-((4-((2-(Methyl(2-pyridinyl)amino)ethyl)oxy)phenyl)methylidene)-1,3-thiazolidine-2,4-dione;C18 H17 N3 O3 S;ROSIGLITAZONE TARTRATE IMPURITY I;(5Z)-didehydro rosiglitazone;SCHEMBL2260054;2,4-tiazolidinadiona, 5-[[4-[2-(metil-2-piridinilamino)etoxi]fenil]metileno]-;5-[4-[2-[N-Methyl-N-(2-pyridinyl)amino]ethoxy]-benzylidene]-2,4-thiazolidinedione;DTXSID101128074;ROSIGLITAZONETARTRATEIMPURITYI;BDBM50049242;AKOS025402034;AC-3462;Q27268428;(5Z)-5-[[4-[2-(Methyl-2-pyridinylamino)ethoxy]phenyl]methylene]-2,4-thiazolidinedione;4-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methylidene]-1,3-thiazolidine-2,5-dione;5-[(Z)-4-[2-[Methyl(2-pyridyl)amino]ethoxy]benzylidene]thiazolidine-2,4-dione;(z)-5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]-methylene]-1,3-thiazolidine-2,4-dione;5-[1-{4-[2-(Methyl-pyridin-2-yl-amino)-ethoxy]-phenyl}-meth-(Z)-ylidene]-thiazolidine-2,4-dione

Chemical Property of Didehydro rosiglitazone, (5Z)-

Chemical Property:

• PSA: 100.32000
• LogP: 3.19660
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 355.09906259
• Heavy Atom Count: 25
• Complexity: 518

Purity/Quality:

99.90% ^*data from raw suppliers

(5Z)-Rosiglitazone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(CCOC1=CC=C(C=C1)C=C2C(=O)NC(=O)S2)C3=CC=CC=N3
• Isomeric SMILES: CN(CCOC1=CC=C(C=C1)/C=C\2/C(=O)NC(=O)S2)C3=CC=CC=N3
• Uses: (5Z)-Rosiglitazone is the Z-isomer of Rosiglitazone (R693500), an insulin sensitizer; binds to peroxisome proliferator activated receptor gamma (PPAR- γ).

Technology Process of Didehydro rosiglitazone, (5Z)-

There total 15 articles about Didehydro rosiglitazone, (5Z)- 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: 99.0%

thiazoline-2,4-dione (2295-31-0) + 4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde (122321-03-3) → (Z)-5-[4-[2-[N-methyl-N-(pyridin-2-yl)amino]ethoxy]benzylidene]thiazolidine-2,4-dione (160596-25-8)

Guidance literature:

With piperazinomethyl polystyrene; In toluene; at 88 ℃; for 24h;

DOI:10.1039/b307549d

Reference yield: 71.0%

2-chloropyridine (109-09-1) + (Z)-5-(4-(2-(methylamino)ethoxy)benzylidene)thiazolidine-2,4-dione → (Z)-5-[4-[2-[N-methyl-N-(pyridin-2-yl)amino]ethoxy]benzylidene]thiazolidine-2,4-dione (160596-25-8)

Guidance literature:

With C₄₈H₅₆ClN₃Pd; potassium tert-butylate; In tetrahydrofuran; at 80 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1002/asia.201700877

Reference yield:

→ (Z)-5-[4-[2-[N-methyl-N-(pyridin-2-yl)amino]ethoxy]benzylidene]thiazolidine-2,4-dione (160596-25-8) + rosiglitazone (122320-73-4)

Guidance literature:

upstream raw materials:

thiazoline-2,4-dione

4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

2-fluoropyridine

4-hydroxy-benzaldehyde

Downstream raw materials:

rosiglitazone