Pioglitazone N-Oxide

Base Information

• Chemical Name: Pioglitazone N-Oxide
• CAS No.: 145350-09-0
• Molecular Formula: C19H20N2O4S
• Molecular Weight: 372.445
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30443587
• Nikkaji Number: J762.724F
• Mol file: 145350-09-0.mol

Synonyms:Pioglitazone N-Oxide;145350-09-0;5-[[4-[2-(5-ethyl-1-oxidopyridin-1-ium-2-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;PioglitazoneN-Oxide;SCHEMBL9545736;DTXSID30443587;YTKQAGFCVMHNHM-UHFFFAOYSA-N;Pioglitazone-d4 N-Oxide (deuterated);AKOS030255781;2-(2-(4-((2,4-dioxothiazolidin-5-yl)methyl)phenoxy)ethyl)-5-ethylpyridine 1-oxide;AS-18997;FT-0673908;A909414;J-008091;rac-2-(2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxy}ethyl)-5-ethylpyridine-1-oxide;5-[[4-[2-(5-Ethyl-1-oxido-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione;2,4-Thiazolidinedione, 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-, N-oxide;Pioglitazone N-oxide

Chemical Property of Pioglitazone N-Oxide

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 158-160 °C
• Refractive Index: 1.64
• Boiling Point: 666.324 °C at 760 mmHg
• PKA: 6.34±0.50(Predicted)
• Flash Point: 356.78 °C
• PSA: 106.16000
• Density: 1.329 g/cm³
• LogP: 3.52190
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 372.11437830
• Heavy Atom Count: 26
• Complexity: 496

Purity/Quality:

98%, ^*data from raw suppliers

PioglitazoneN-Oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=C[N+](=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3)[O-]
• Uses: A metabolite of Pioglitazone (P471000).

Technology Process of Pioglitazone N-Oxide

There total 3 articles about Pioglitazone N-Oxide 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: 96.0%

Pioglitazone (105355-27-9,111025-46-8) → rac-2-(2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxy}ethyl)-5-ethylpyridine-1-oxide (145350-09-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; Ambient temperature;

DOI:10.1021/jm9605694

Reference yield: 46.2%

rac-5-({p-[2-(5-ethyl-2-pyridyl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione hydrochloride → rac-2-(2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxy}ethyl)-5-ethylpyridine-1-oxide (145350-09-0)

Guidance literature:

rac-5-({p-[2-(5-ethyl-2-pyridyl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione hydrochloride; With sodium hydrogencarbonate; In water; N,N-dimethyl-formamide;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 10 - 20 ℃; for 50h;

Reference yield:

5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride (112529-15-4) → rac-2-(2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxy}ethyl)-5-ethylpyridine-1-oxide (145350-09-0)

Guidance literature:

With dihydrogen peroxide; at 60 - 80 ℃; for 24h;

DOI:10.1691/ph.2010.9239

upstream raw materials:

Pioglitazone

5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride

Downstream raw materials:

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

5-{4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione

Refernces

• 1、 -. "Pioglitazone impurity preparation method". Paragraph 0015-0023. . Retrieved 2017/04/29.
• 2、 Ramulu,Thilak Kumar,Radha Krishna,Vasudev,Kaviraj,Rao,Someswara Rao. "Identification, isolation and characterization of potential degradation products in pioglitazone hydrochloride drug substance". experimental part. p. 162 - 168. Retrieved 2011/08/05.