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122320-73-4

Basic Information
CAS No.: 122320-73-4
Name: 2,4-Thiazolidinedione,5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-
Article Data: 46
Cas Database
Molecular Structure:
Molecular Structure of 122320-73-4 (2,4-Thiazolidinedione,5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-)
Formula: C18H19N3O3S
Molecular Weight: 357.433
Synonyms: 5-[4-[2-(N-Methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione;5-[[4-[2-[N-Methyl-N-(2-pyridyl)amino]ethoxy]phenyl]methyl]thiazolidine-2,4-dione;BRL 49653;Rosiglizole;TDZ 01;
EINECS: 924-121-1
Density: 1.315 g/cm3
Melting Point: 153-155 °C
Boiling Point: 585 °C at 760mmHg
Flash Point: 307.6 °C
Solubility: N/A
Appearance: White to off-white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/38
Safety: 26-37/39
Transport Information: N/A
PSA: 96.83000
LogP: 2.81970
Synthetic route
160596-25-8

(Z)-5-[4-[2-[N-methyl-N-(pyridin-2-yl)amino]ethoxy]benzylidene]thiazolidine-2,4-dione

122320-73-4

rosiglitazone

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 2585.81 Torr; for 24h;100%
With methanol; iodine; magnesium at 20℃;95%
With sodium hydroxide; sodium tetrahydroborate; butane-2,3-dione dioxime; cobalt(II) chloride In water; N,N-dimethyl-formamide at 55℃; for 4.41667h;93%
105355-27-9

Pioglitazone

122320-73-4

rosiglitazone

Conditions
ConditionsYield
In ethanol at 50 - 80℃;95%
In acetonitrile at 50 - 70℃;90%
122320-74-5

5-{4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzylidene}thiazolin-2,4-dione

122320-73-4

rosiglitazone

Conditions
ConditionsYield
With BuMnCl In methanol at 20℃; for 0.5h;93.7%
With iodine; magnesium In methanol for 3h; Reflux;92%
With pyridine; lithium borohydride In tetrahydrofuran; water77%

5-{-4-[2-(N-methyl-N-(2-pyridyl)-amino)-ethoxy]-benzylidene}-2,4-thiazolidinedione

122320-73-4

rosiglitazone

Conditions
ConditionsYield
With sodium tetrahydroborate; butane-2,3-dione-bis-methylimine; sodium hydroxide; cobaltous chloride hexahydrate In polyethylene glycol-400 (PEG-400); water; N,N-dimethyl-formamide at 0 - 15℃; Product distribution / selectivity;90%
Stage #1: 5-{-4-[2-(N-methyl-N-(2-pyridyl)-amino)-ethoxy]-benzylidene}-2,4-thiazolidinedione With hydrogen; trifluoroacetic acid; palladium 10% on activated carbon In water; acetic acid at 69 - 71℃; under 3800.26 - 4560.31 Torr; for 12 - 15h;
Stage #2: With potassium hydroxide In methanol; water for 0.5h; Heating / reflux;
84.6%
Stage #1: 5-{-4-[2-(N-methyl-N-(2-pyridyl)-amino)-ethoxy]-benzylidene}-2,4-thiazolidinedione With sodium hydroxide; butane-2,3-dione dioxime; cobalt(II) chloride In tetrahydrofuran; water at 10℃;
Stage #2: With sodium hydroxide; sodium tetrahydroborate In tetrahydrofuran; water at 10 - 25℃; for 17.5h;
Stage #3: With acetic acid In tetrahydrofuran; water for 2.5 - 3.5h;
With hydrogen; palladium 10% on activated carbon In 1,4-dioxane at 20℃; under 760.051 Torr; Product distribution / selectivity;
Stage #1: 5-{-4-[2-(N-methyl-N-(2-pyridyl)-amino)-ethoxy]-benzylidene}-2,4-thiazolidinedione With sodium hydroxide; sodium tetrahydroborate; butane-2,3-dione dioxime; cobalt(II) chloride In tetrahydrofuran; water at 10 - 25℃; for 17.5h;
Stage #2: With acetic acid In tetrahydrofuran; water for 2.5 - 3.5h; Product distribution / selectivity;
2295-31-0

2,4-thiazolidinedion

122321-03-3

4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

122320-73-4

rosiglitazone

Conditions
ConditionsYield
Stage #1: thiazoline-2,4-dione; 4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde With pyrrolidine; acetic acid In toluene at 110℃; for 2h;
Stage #2: With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; silica gel In toluene for 13h; Product distribution / selectivity; Heating / reflux;
58%
2295-31-0

2,4-thiazolidinedion

372-48-5

2-fluoropyridine

123-08-0

4-hydroxy-benzaldehyde

147687-15-8

N-Fmoc-N-methyl-2-aminoethanol

122320-73-4

rosiglitazone

Conditions
ConditionsYield
Yield given; Multistep reaction;
2295-31-0

2,4-thiazolidinedion

4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzaldehyde sodium metabisulphite complex

122320-73-4

rosiglitazone

Conditions
ConditionsYield
piperidine; acetic acid In toluene for 5 - 6h; Product distribution / selectivity; Heating / reflux;
With sodium hydroxide In toluene for 18h; Product distribution / selectivity; Heating / reflux;
122320-74-5

5-{4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzylidene}thiazolin-2,4-dione

L-Selectride

122320-73-4

rosiglitazone

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; dihydrogen peroxide In tetrahydrofuran

(5Z)-5-(4-fluorobenzylidene)-1,3-thiazolidine-2,4-dione

122321-04-4

2-(N-methyl-N-(pyridin-2-yl)amino)ethanol

122320-73-4

rosiglitazone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / dimethyl sulfoxide / 4 h / 100 °C
2: iodine; magnesium / methanol / 3 h / Reflux
View Scheme
109-09-1

2-chloropyridine

122320-73-4

rosiglitazone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 13 h / 120 °C / Neat (no solvent)
2: potassium carbonate / dimethyl sulfoxide / 4 h / 100 °C
3: iodine; magnesium / methanol / 3 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: 13 h / 120 °C / Neat (no solvent)
2: sodium hydride / N,N-dimethyl-formamide / 80 °C
3: piperidine / toluene / 2 h / 80 °C
4: iodine; magnesium / methanol / 3 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: 9 h / Reflux
2.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere
2.2: 24 h / 24 - 50 °C / Inert atmosphere
3.1: piperidine / toluene / 6 h / Inert atmosphere; Reflux
4.1: sodium hydroxide; cobalt(II) chloride hexahydrate; butane-2,3-dione dioxime; sodium tetrahydroborate / water / 24 h / 20 °C / pH 11
View Scheme
Multi-step reaction with 4 steps
1: 9 h / Reflux
2: tetrabutylammomium bromide; potassium hydroxide / water; toluene / 0.67 h / 80 °C / Microwave irradiation
3: piperidine / toluene / 6 h / Inert atmosphere; Reflux
4: sodium hydroxide; cobalt(II) chloride hexahydrate; butane-2,3-dione dioxime; sodium tetrahydroborate / water / 24 h / 20 °C / pH 11
View Scheme
Multi-step reaction with 4 steps
1: triphenylmethyl sodium / 8 h / 70 °C
2: potassium hexamethylsilazane / 1 h / 60 °C
3: toluene / 5 h / Reflux
4: BuMnCl / methanol / 0.5 h / 20 °C
View Scheme
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    Overview Quick Details CAS No.: 122320-73-4 Other Names: Rosiglitazone MF: C6H13N3O3, C18H19N

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Specification

The IUPAC name of Rosiglitazone is 5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione. With the CAS registry number 122320-73-4, it is also named as 2,4-Thiazolidinedione, 5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-. The product's categories are Active Pharmaceutical Ingredients; Rosiglitazone; API's. It is an anti-diabetic drug in the thiazolidinedione class of drugs. Thiazolidinediones act as insulin sensitizers. But the drug is controversial in the U.S. Food and Drug Administration.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.56; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.5; (4)ACD/LogD (pH 7.4): 1.47; (5)ACD/BCF (pH 5.5): 4.5; (6)ACD/BCF (pH 7.4): 4.2; (7)ACD/KOC (pH 5.5): 50.98; (8)ACD/KOC (pH 7.4): 47.61; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.641; (13)Molar Refractivity: 98.06 cm3; (14)Molar Volume: 271.6 cm3; (15)Polarizability: 38.87×10-24 cm3; (16)Surface Tension: 60.5 dyne/cm; (17)Enthalpy of Vaporization: 87.4 kJ/mol; (18)Vapour Pressure: 1.14E-13 mmHg at 25°C; (19)Rotatable Bond Count: 7; (20)Tautomer Count: 5; (21)Exact Mass: 357.114712; (22)MonoIsotopic Mass: 357.114712; (23)Topological Polar Surface Area: 96.8; (24)Heavy Atom Count: 25; (25)Complexity: 469.

Preparation of Rosiglitazone: 2-N-Methyl-2-pyridylaminoethanol dissolves in dimethylformamide, and adding sodium hydride in batches under nitrogen atmosphere. When the violent reaction is slowed down, add 4-fluorobenzaldehyde. The treated compound and 2,4-thiazoline dione dissolves in toluene. Adding piperidine acetate and refluxing. The treated compound dissolves in dioxane. In the role of a catalyst, they are hydrogenated at room temperature and atmospheric pressure. After filtration, vacuum concentration and recrystallization, we can get the product.


Uses of Rosiglitazone: It have an anti-inflammatory effect in addition to its effect on insulin resistance. It also benefits patients with Alzheimer's disease who do not express the ApoE4 allele. In addition, this drug may also treat mild to moderate Ulcerative Colitis, due to its antiinflammatory properties as a PPAR ligand.

Side-effects and contraindications of Rosiglitazone:
1. A press release by GlaxoSmithKline in February 2007 noted that there is a greater incidence of fractures of the upper arms, hands and feet in female diabetics given rosiglitazone compared with those given metformin or glyburide.
2. A meta-analysis reported in May 2007 that the use of rosiglitazone was associated with a significantly increased risk of heart attack.
3. As early as September 2005, both Rosiglitazone and Pioglitazone have been suspected of causing Macular Edema, which causes partial blindness in various spots of the angle of vision.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C1NC(=O)SC1Cc3ccc(OCCN(c2ncccc2)C)cc3
2. InChI:InChI=1/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)