Carboxy Pioglitazone (M-V)

Base Information

• Chemical Name: Carboxy Pioglitazone (M-V)
• CAS No.: 146062-48-8
• Molecular Formula: C19H18N2O5S
• Molecular Weight: 386.42162
• UNII: RK29UX2P6A
• DSSTox Substance ID: DTXSID30435149
• Nikkaji Number: J601.467D
• ChEMBL ID: CHEMBL357393
• Mol file: 146062-48-8.mol

Synonyms:Carboxy Pioglitazone (M-V);146062-48-8;Pioglitazone Metabolite M5;RK29UX2P6A;UNII-RK29UX2P6A;2-[6-[2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]ethyl]pyridin-3-yl]acetic Acid;3-Pyridineacetic acid, 6-(2-(4-((2,4-dioxo-5-thiazolidinyl)methyl)phenoxy)ethyl)-;146062-68-2;CHEMBL357393;SCHEMBL5669985;DTXSID30435149;OIQJTMMAMWFMQR-UHFFFAOYSA-N;FT-0664344;U-91323;A1-01709

Chemical Property of Carboxy Pioglitazone (M-V)

Chemical Property:

• Melting Point: 146-148 °C
• Boiling Point: 665.5±55.0 °C(Predicted)
• PKA: 3.63±0.10(Predicted)
• PSA: 134.38000
• Density: 1.393±0.06 g/cm3(Predicted)
• LogP: 2.50020
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 386.09364285
• Heavy Atom Count: 27
• Complexity: 550

Purity/Quality:

98% ^*data from raw suppliers

CarboxyPioglitazone(M-V) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC2C(=O)NC(=O)S2)OCCC3=NC=C(C=C3)CC(=O)O
• Uses: A metabolite of the antidiabetic Pioglitazone (P471000).

Technology Process of Carboxy Pioglitazone (M-V)

There total 17 articles about Carboxy Pioglitazone (M-V) 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: 79.0%

5-<4-<2-(5-cyanomethyl-2-pyridyl)ethoxy>benzyl>-2-imino-4-thiazolidinone (146062-68-2) → (+/-)-5-benzyl>-2,4-thiazolinedione (146062-48-8)

Guidance literature:

With hydrogenchloride; for 24h; Heating;

DOI:10.1248/cpb.43.2168

Reference yield: 72.0%

(6-{2-[4-(2,4-Dioxo-thiazolidin-5-ylmethyl)-phenoxy]-ethyl}-pyridin-3-yl)-acetonitrile (184766-98-1) → (+/-)-5-benzyl>-2,4-thiazolinedione (146062-48-8)

Guidance literature:

With hydrogenchloride; for 18h; Heating;

DOI:10.1021/jm9605694

Reference yield:

3-((methoxymethoxy)methyl)-6-methylpyridine (146062-61-5) → (+/-)-5-benzyl>-2,4-thiazolinedione (146062-48-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 29 percent / H₂O / 5 h / 150 °C

2: 58 percent / diethyl azodicarboxylate, Ph₃P / tetrahydrofuran / 18 h / Ambient temperature

3: 96 percent / 2N aq. HCl / methanol / 2 h / Heating

4: SOCl₂ / CHCl₃ / 1 h / Heating

5: dimethylformamide / 1 h / Ambient temperature

6: 65 percent / piperidine / ethanol / 18 h / Heating

7: 56 percent / NaBH₄, 1.0N aq. NaOH, CoCl₂*6H₂O, 2,2'-dipyridyl / dimethylformamide; tetrahydrofuran / 18 h / Ambient temperature

8: 72 percent / 4N aq. HCl / 18 h / Heating

With piperidine; hydrogenchloride; [2,2]bipyridinyl; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; triphenylphosphine; cobalt(II) chloride; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1021/jm9605694

upstream raw materials:

5-<4-<2-(5-cyanomethyl-2-pyridyl)ethoxy>benzyl>-2-imino-4-thiazolidinone

(6-{2-[4-(2,4-Dioxo-thiazolidin-5-ylmethyl)-phenoxy]-ethyl}-pyridin-3-yl)-acetonitrile

6-methyl-3-pyridinemethanol

Methyl 6-methylnicotinate

Downstream raw materials:

4-azido-N-[2-({[6-(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)pyridin-3-yl]acetyl}amino)ethyl]-2-hydroxybenzamide

Refernces

• 1、 Sohda,Ikeda,Meguro. "Studies on antidiabetic agents. XII. Synthesis and activity of the metabolites of (±)-5-[p-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl]-2,4- thiazolidinedione (pioglitazone)". . p. 2168 - 2172. Retrieved 2007/10/03.