5-(4-(2-(5-Ethylpyridin-2-yl)-2-hydroxyethoxy)benzyl)thiazolidine-2,4-dione

Base Information

• Chemical Name: 5-(4-(2-(5-Ethylpyridin-2-yl)-2-hydroxyethoxy)benzyl)thiazolidine-2,4-dione
• CAS No.: 101931-00-4
• Molecular Formula: C19H20N2O4S
• Molecular Weight: 372.445
• UNII: M77TY40AOT
• DSSTox Substance ID: DTXSID20432066
• Nikkaji Number: J699.845C
• ChEMBL ID: CHEMBL1270
• Mol file: 101931-00-4.mol

Synonyms:101931-00-4;HYDROXY PIOGLITAZONE (M-II);5-(4-(2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy)benzyl)thiazolidine-2,4-dione;2-Hydroxypioglitazone;5-[[4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;M77TY40AOT;5-[[4-[2-(5-ETHYL-2-PYRIDINYL)-2-HYDROXYETHOXY] PHENYL]METHYL]-2,4-THIAZOLIDINEDIONE;Hydroxy Pioglitazone (M-II) (Mixture of Diastereomers);2,4-Thiazolidinedione, 5-((4-(2-(5-ethyl-2-pyridinyl)-2-hydroxyethoxy)phenyl)methyl)-;5-((4-(2-(5-Ethyl-2-pyridinyl)-2-hydroxyethoxy)phenyl)methyl)-2,4-thiazolidinedione;5-[[4-[2-(5-Ethyl-2-pyridinyl]-2-hydroxyethoxy]phenyl]methyl]-2,4-thiazolidinedione;5-[4-[2-(5-ethyl-2-pyridyl)-2-hydroxyethoxy]benzyl]-2,4-thiazolidinedione;5-{4-[2-(5-ethyl-2-pyridyl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione;5-({4-[2-(5-ETHYLPYRIDIN-2-YL)-2-HYDROXYETHOXY]PHENYL}METHYL)-1,3-THIAZOLIDINE-2,4-DIONE;Hydroxy pioglitazone(m-ii);UNII-M77TY40AOT;CHEMBL1270;Pioglitazone, hydroxyl M-II;SCHEMBL2327405;DTXSID20432066;FT-0670013;Hydroxy Pioglitazone-d4 (M-II) (deuterated);U-90760;J-000524;5-({p-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

Chemical Property of 5-(4-(2-(5-Ethylpyridin-2-yl)-2-hydroxyethoxy)benzyl)thiazolidine-2,4-dione

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 125-140 (sub)oC
• Boiling Point: 627.617oC at 760 mmHg
• Flash Point: 333.371oC
• PSA: 113.82000
• Density: 1.325g/cm3
• LogP: 2.97930
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 372.11437830
• Heavy Atom Count: 26
• Complexity: 496

Purity/Quality:

97% ^*data from raw suppliers

HydroxyPioglitazone(M-II)(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=CN=C(C=C1)C(COC2=CC=C(C=C2)CC3C(=O)NC(=O)S3)O
• Uses: A metabolite of Pioglitazone (P471000).

Technology Process of 5-(4-(2-(5-Ethylpyridin-2-yl)-2-hydroxyethoxy)benzyl)thiazolidine-2,4-dione

There total 26 articles about 5-(4-(2-(5-Ethylpyridin-2-yl)-2-hydroxyethoxy)benzyl)thiazolidine-2,4-dione 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: 95.0%

5-{4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]benzylidene}-2,4-thiazolidene dione (646519-84-8) → 5-{4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione (101931-00-4)

Guidance literature:

With sodium tetrahydroborate; cobalt(II) chloride hexahydrate; butane-2,3-dione dioxime; In water; N,N-dimethyl-formamide; at 65 - 85 ℃; for 4h; Temperature; Time; Large scale;

Reference yield: 46.0%

rac-2-(2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxy}ethyl)-5-ethylpyridine-1-oxide (145350-09-0) → 5-{4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione (101931-00-4)

Guidance literature:

With trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; at 50 ℃; for 48h;

Reference yield:

4-[2-(5-ethylpyridin-2-yl)ethoxy]aniline (85583-40-0) → 5-{4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione (101931-00-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.)47percent HBr, NaNO₂, 2.)Cu₂O / 1.)MeOH, H₂O, 5 deg C, 20 min., 2.)40 deg C

2: 70percent m-chloroperbenzoic acid / methanol / Heating

3: 80 °C

4: NaOAc / ethanol / Heating

5: 3N HCl / Heating

With copper(I) oxide; hydrogenchloride; hydrogen bromide; sodium acetate; 3-chloro-benzenecarboperoxoic acid; sodium nitrite; In methanol; ethanol;

upstream raw materials:

rac-2-(2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxy}ethyl)-5-ethylpyridine-1-oxide

Pioglitazone

5-ethyl-2-(2-hydroxyethyl)pyridine

4-[2-(5-ethylpyridin-2-yl)ethoxy]aniline

Downstream raw materials:

rac-5-({p-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

5-(4-hydroxybenzyl)-2,4-thiazolidinedione

Pioglitazone

5-{4-[2-(5-ethylpyridin-2-yl)-2-mesylethoxy]benzylidene}-2,4-thiazolidene dione

Refernces

• 1、 -. "NOVEL PROCESS TO PREPARE PIOGLITAZONE VIA SEVERAL NOVEL INTERMEDIATES". . . Retrieved 2014/04/03.
• 2、 Carpenter, Donald E.,Imbordino, Rick J.,Maloney, Mark T.,Moeslein, Jeffery A.,Reeder, Michael R.,Scott, Allen. "Process development and scale-up of the potential thiazolidinedione antidiabetic candidate PNU-91325". . p. 721 - 728. Retrieved 2013/09/06.