Ketopioglitazone

Base Information

• Chemical Name: Ketopioglitazone
• CAS No.: 146062-45-5
• Molecular Formula: C₁₉H₁₈N₂O₄S
• Molecular Weight: 370.429
• UNII: S7979UT55L
• ChEMBL ID: CHEMBL1268
• DSSTox Substance ID: DTXSID50409544
• Nikkaji Number: J699.846A
• Mol file: 146062-45-5.mol

Synonyms:146062-45-5;Ketopioglitazone;Keto Pioglitazone;Keto Pioglitazone (M-III);Pioglitazone metabolite M3;5-(4-(2-(5-Acetylpyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione;Keto pioglitazone-d4 (M-III);S7979UT55L;5-[[4-[2-(5-Acetyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4thiazolidinedione;2,4-Thiazolidinedione, 5-[[4-[2-(5-acetyl-2-pyridinyl)ethoxy]phenyl]methyl]-;5-[[4-[2-(5-acetylpyridin-2-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;5-((4-(2-(5-Acetyl-2-pyridinyl)ethoxy)phenyl)methyl)-2,4-thiazolidinedione;5-[[4-[2-(5-acetyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione;2,4-Thiazolidinedione, 5-((4-(2-(5-acetyl-2-pyridinyl)ethoxy)phenyl)methyl)-;Pioglitazone ketone;Keto-Pioglitazone (M-III);5-({4-[2-(5-acetylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione;Pioglitazone, ketone;CHEMBL1268;UNII-S7979UT55L;SCHEMBL5805530;DTXSID50409544;JMLKLMFMQRAJNI-UHFFFAOYSA-N;AKOS015837762;FT-0643389;A1-01708;J-008188;5-[4-[2-(5-acetyl-2-pyridyl)ethoxy]benzyl]-2,4-thiazolidinedione

Chemical Property of Ketopioglitazone

Chemical Property:

• Vapor Pressure: 1.75E-15mmHg at 25°C
• Melting Point: 113-115 °C
• Refractive Index: 1.618
• Boiling Point: 623.8 °C at 760 mmHg
• PKA: 6.35±0.50(Predicted)
• Flash Point: 331.1 °C
• PSA: 110.66000
• Density: 1.315 g/cm³
• LogP: 3.12860
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 370.09872823
• Heavy Atom Count: 26
• Complexity: 534

Purity/Quality:

98%Min ^*data from raw suppliers

Keto Pioglitazone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3

Technology Process of Ketopioglitazone

There total 16 articles about Ketopioglitazone 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: 98.0%

5-(4-{2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-ethoxy}-benzyl)-thiazolidine-2,4-dione (184766-66-3) → Ketopioglitazone (146062-45-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 18h; Ambient temperature;

DOI:10.1021/jm9605694

Reference yield: 63.0%

Hydroxypioglitazone (146062-44-4) → Ketopioglitazone (146062-45-5)

Guidance literature:

With pyridinium chlorochromate; In tetrahydrofuran; at 20 ℃; for 12h;

Reference yield:

1-(6-methyl-pyridin-3-yl)-ethanone (36357-38-7) → Ketopioglitazone (146062-45-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / pTsOH / toluene / 8 h / Heating

2: 24 percent / H₂O / 5 h / 150 °C

3: 55 percent / diethyl azodicarboxylate, Ph₃P / tetrahydrofuran / 18 h / Ambient temperature

4: 56 percent / piperidine / ethanol / 18 h / Heating

5: 96 percent / NaBH₄, 1.0N aq. NaOH, CoCl₂*6H₂O, dimethylglyoxime / dimethylformamide; tetrahydrofuran / 18 h / Ambient temperature

6: 98 percent / 4N aq. HCl / tetrahydrofuran / 18 h / Ambient temperature

With piperidine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; Dimethylglyoxime; toluene-4-sulfonic acid; triphenylphosphine; cobalt(II) chloride; diethylazodicarboxylate; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm9605694

upstream raw materials:

Hydroxypioglitazone

5-(4-{2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-ethoxy}-benzyl)-thiazolidine-2,4-dione

1-(6-methyl-pyridin-3-yl)-ethanone

Methyl 6-methylnicotinate

Refernces

• 1、 Tanis, Steven P.,Parker, Timothy T.,Colca, Jerry R.,Fisher, Roberta M.,Kletzein, Rolf F.. "Synthesis and biological activity of metabolites of the antidiabetic, antihyperglycemic agent pioglitazone". . p. 5053 - 5063. Retrieved 2007/10/03.
• 2、 -. "Thiazolidinedione derivatives, production and use thereof". . . Retrieved 2008/06/13.