2,4-Thiazolidinedione, 5-((4-(2-((6-(4-methoxyphenoxy)-4-pyrimidinyl)methylamino)ethoxy)phenyl)methyl)-, (R)-

Base Information

• Chemical Name: 2,4-Thiazolidinedione, 5-((4-(2-((6-(4-methoxyphenoxy)-4-pyrimidinyl)methylamino)ethoxy)phenyl)methyl)-, (R)-
• CAS No.: 607723-33-1
• Molecular Formula: C24H24N4O5S
• Molecular Weight: 480.54
• UNII: CMJ85U3371
• DSSTox Substance ID: DTXSID50976246
• Wikidata: Q27275535
• Mol file: 607723-33-1.mol

Synonyms:(R)-lobeglitazone;LOBEGLITAZONE, (R)-;SCHEMBL20125580;DTXSID50976246;CMJ85U3371;NS00072031;Q27275535;2,4-THIAZOLIDINEDIONE, 5-((4-(2-((6-(4-METHOXYPHENOXY)-4-PYRIMIDINYL)METHYLAMINO)ETHOXY)PHENYL)METHYL)-, (R)-;4-Hydroxy-5-{[4-(2-{[6-(4-methoxyphenoxy)pyrimidin-4-yl](methyl)amino}ethoxy)phenyl]methyl}-1,3-thiazol-2(5H)-one

Chemical Property of 2,4-Thiazolidinedione, 5-((4-(2-((6-(4-methoxyphenoxy)-4-pyrimidinyl)methylamino)ethoxy)phenyl)methyl)-, (R)-

Chemical Property:

• Melting Point: 165-167 °C
• Boiling Point: 711.0±60.0 °C(Predicted)
• PKA: 6.35±0.50(Predicted)
• PSA: 128.18000
• Density: 1.336±0.06 g/cm3(Predicted)
• LogP: 4.01560
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 480.14674105
• Heavy Atom Count: 34
• Complexity: 670

Purity/Quality:

98% ^*data from raw suppliers

LOBEGLITAZONE 95.00% ^*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)CC2C(=O)NC(=O)S2)C3=CC(=NC=N3)OC4=CC=C(C=C4)OC
• Isomeric SMILES: CN(CCOC1=CC=C(C=C1)C[C@@H]2C(=O)NC(=O)S2)C3=CC(=NC=N3)OC4=CC=C(C=C4)OC
• Uses: Lobeglitazone is used in anti-diabetes mellitus pharmacological management.

Technology Process of 2,4-Thiazolidinedione, 5-((4-(2-((6-(4-methoxyphenoxy)-4-pyrimidinyl)methylamino)ethoxy)phenyl)methyl)-, (R)-

There total 6 articles about 2,4-Thiazolidinedione, 5-((4-(2-((6-(4-methoxyphenoxy)-4-pyrimidinyl)methylamino)ethoxy)phenyl)methyl)-, (R)- 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: 89.0%

5-[4-(2-{[6-(4-methoxyphenoxy)pyrimidin-4-yl]methylamino}ethoxy)benzylidene]thiazolidine-2,4-dione → 5-(4-{2-[6-(4-methoxyphenoxy)pyrimidin-4-yl]methylamino ethoxy}benzyl)thiazolidine-2,4-dione (607723-33-1)

Guidance literature:

With hydrogen; palladium dihydroxide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.ejmech.2005.03.019

Reference yield:

4-chloro-6-(4-methoxyphenoxy)pyrimidine (607723-54-6) → 5-(4-{2-[6-(4-methoxyphenoxy)pyrimidin-4-yl]methylamino ethoxy}benzyl)thiazolidine-2,4-dione (607723-33-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / ethanol / Heating

2: 68 percent / sodium hydride / dimethylformamide / 20 °C

3: 68 percent / piperidine / ethanol / Heating

4: 89 percent / hydrogen / Pd(OH)2/C / dimethylformamide / 20 °C

With piperidine; hydrogen; sodium hydride; palladium dihydroxide; In ethanol; N,N-dimethyl-formamide; 3: Knoevenagel condensation;

DOI:10.1016/j.ejmech.2005.03.019

Reference yield:

2-{[6-(4-methoxyphenoxy)pyrimidin-4-yl]methylamino}ethanol (607723-69-3) → 5-(4-{2-[6-(4-methoxyphenoxy)pyrimidin-4-yl]methylamino ethoxy}benzyl)thiazolidine-2,4-dione (607723-33-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / sodium hydride / dimethylformamide / 20 °C

2: 68 percent / piperidine / ethanol / Heating

3: 89 percent / hydrogen / Pd(OH)2/C / dimethylformamide / 20 °C

With piperidine; hydrogen; sodium hydride; palladium dihydroxide; In ethanol; N,N-dimethyl-formamide; 2: Knoevenagel condensation;

DOI:10.1016/j.ejmech.2005.03.019

upstream raw materials:

4-chloro-6-(4-methoxyphenoxy)pyrimidine

2-{[6-(4-methoxyphenoxy)pyrimidin-4-yl]methylamino}ethanol

4-({2-[6-(4-methoxyphenoxy)pyrimidin-4-yl]methylamino}ethoxy)benzaldehyde

4-methoxy-phenol