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Pioglitazone hydrochloride
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Name

Pioglitazone hydrochloride

 EINECS 629-731-9
CAS No. 112529-15-4 Density 1.26 g/cm3
PSA 93.59000 LogP 4.29040
Solubility soluble in N,N-dimethylformamide, slightly soluble in anhydrous ethanol, very slightly soluble in acetone and acetonitrile, practically insoluble in water, and insoluble in ether Melting Point 193-194 ºC
Formula C19H21ClN2O3S Boiling Point 575.4 ºC at 760 mmHg
Molecular Weight 392.906 Flash Point 301.8 ºC
Transport Information N/A Appearance white crystals or crystalline powder
Safety 22-24/25 Risk Codes 36/38
Molecular Structure Molecular Structure of 112529-15-4 ([5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-] thiazolidinedione hydrochloride) Hazard Symbols IrritantXi
Synonyms

(+-)-5-(p-(2-(5-Ethyl-2-pyridyl)ethoxy)benzyl)-2,4-thiazolidinedione monohydrochloride;Actos;2,4-Thiazolidinedione,5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-, monohydrochloride (9CI);2,4-Thiazolidinedione, 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-,monohydrochloride, (?à)-;5-[4-[2-(5-Ethyl-2-pyridyl)ethoxy]benzyl]thiazolidine-2,4-dionehydrochloride;Pioglitazone HCl;

Article Data 16

Pioglitazone hydrochloride Synthetic route

105355-27-9

Pioglitazone

112529-15-4

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

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 10 - 65℃; for 4.25h; Product distribution / selectivity;95%
With hydrogenchloride In ethanol; water at 10 - 65℃; for 4.25h; Product distribution / selectivity;90%
With hydrogenchloride In methanol; water at 20℃; for 1h;90.5%

5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methylene]-thiazolidine-2,4-dione hydrogen chloride

112529-15-4

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

Conditions
ConditionsYield
Stage #1: 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methylene]-thiazolidine-2,4-dione hydrogen chloride With hydrogen; palladium 10% on activated carbon In methanol; water at 50 - 60℃; under 3750.38 - 4500.45 Torr; for 15h;
Stage #2: With hydrogenchloride In water at 0 - 5℃; for 3h;		84%
5223-06-3

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

112529-15-4

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 63 percent / NaH / dimethylformamide
2: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature
3: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C
4: 53 percent / NaOAc / ethanol / Heating
5: 2N HCl / 6 h / Heating
6: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 10 steps
1: dihydrogen peroxide / acetic acid / 14 h / 100 °C
2: 0.5 h / 120 °C
3: sodium hydroxide / water / 2 h / 40 °C
4: thionyl chloride; triethylamine / dichloromethane / 1.25 h / 0 - 5 °C
5: N,N-dimethyl-formamide / 14 h / 80 °C
6: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale
7: sodium tetrahydroborate; butane-2,3-dione dioxime; cobalt(II) chloride hexahydrate / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / Large scale
8: triethylamine / dichloromethane / 2 h / 0 °C
9: acetic acid; sodium tetrahydroborate / 15 h / 40 - 45 °C
10: hydrogenchloride / water; ethanol
View Scheme
Multi-step reaction with 10 steps
1: dihydrogen peroxide / acetic acid / 14 h / 100 °C
2: 0.5 h / 120 °C
3: sodium hydroxide / water / 2 h / 40 °C
4: thionyl chloride; triethylamine / dichloromethane / 1.25 h / 0 - 5 °C
5: N,N-dimethyl-formamide / 14 h / 80 °C
6: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale
7: sodium tetrahydroborate; butane-2,3-dione dioxime; cobalt(II) chloride hexahydrate / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / Large scale
8: triethylamine
9: acetic acid; sodium tetrahydroborate / 15 h / 40 - 45 °C
10: hydrogenchloride / water; ethanol
View Scheme
85583-40-0

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

112529-15-4

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C
2: 53 percent / NaOAc / ethanol / Heating
3: 2N HCl / 6 h / Heating
4: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature
View Scheme
85583-54-6

4-(2-(5-ethyl-2-pyridyl)ethoxy)nitrobenzene

112529-15-4

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature
2: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C
3: 53 percent / NaOAc / ethanol / Heating
4: 2N HCl / 6 h / Heating
5: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature
View Scheme
105355-25-7

methyl 2-bromo-3-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]phenyl}propionate

112529-15-4

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 53 percent / NaOAc / ethanol / Heating
2: 2N HCl / 6 h / Heating
3: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature
View Scheme
105355-26-8

5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2-imino-4-thiazolidinone

112529-15-4

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2N HCl / 6 h / Heating
2: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature
View Scheme
With hydrogenchloride; water for 15h; Product distribution / selectivity; Heating / reflux;
Stage #1: 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2-imino-4-thiazolidinone With methanol; oxalic acid In dichloromethane at 20℃; for 0.5h;
Stage #2: With hydrogenchloride; water for 12h; Product distribution / selectivity; Heating / reflux;
350-46-9

4-Fluoronitrobenzene

112529-15-4

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 63 percent / NaH / dimethylformamide
2: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature
3: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C
4: 53 percent / NaOAc / ethanol / Heating
5: 2N HCl / 6 h / Heating
6: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature
View Scheme
674798-32-4

2-bromo-3-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}propionic acid

17356-08-0

thiourea

112529-15-4

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

Conditions
ConditionsYield
Stage #1: 2-bromo-3-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}propionic acid; thiourea With sodium acetate In ethanol for 3h; Heating / reflux;
Stage #2: With hydrogenchloride In ethanol; water for 18h; Heating / reflux;
Stage #3: With ammonia In ethanol; water at 20℃;
1034515-30-4

5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]-benzyl}-2-morpholin-4-yl-thiazol-4-one

112529-15-4

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

Conditions
ConditionsYield
With hydrogenchloride; water; isopropyl alcohol for 8h; Product distribution / selectivity; Heating / reflux;

Pioglitazone hydrochloride Chemical Properties


IUPAC Name: 5-[[4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride
Molecular Formula: C19H21ClN2O3S
Molecular Weight: 392.90 g/mol
Canonical SMILES: CCC1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3.Cl
InChI: InChI=1/C19H20N2O3S.ClH/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17;/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23);1H
Classification Code: Antidiabetic
Product Categories: Active Pharmaceutical Ingredients; Antidiabetic; Diabetes; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds;API's; Pioglitazone
H-Bond Donor: 2
H-Bond Acceptor: 4
Rotatable Bond Count: 7
Tautomer Count: 10
Exact Mass: 392.096141
MonoIsotopic Mass: 392.096141
Topological Polar Surface Area: 68.3
Heavy Atom Count: 26
Complexity: 466
Melting Point: 193-194 °C
Flash Point: 301.8 °C
Enthalpy of Vaporization: 86.19 kJ/mol
Boiling Point: 575.4 °C at 760 mmHg
Vapour Pressure of Pioglitazone HCl (CAS NO.112529-15-4): 3.03E-13 mmHg at 25 °C

Pioglitazone hydrochloride Uses

 Pioglitazone HCl (CAS NO.112529-15-4) is used as an antidiabetic.

Pioglitazone hydrochloride Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/38 
R36/38: Irritating to eyes and skin.
Safety Statements of Pioglitazone HCl (CAS NO.112529-15-4): 22-24/25 
S22: Do not breathe dust. 
S24/25: Avoid contact with skin and eyes.

Pioglitazone hydrochloride Specification

  Pioglitazone HCl (CAS NO.112529-15-4), its Synonyms are 2,4-Thiazolidinedione, 5-((4-(2-(5-ethyl-2-pyridinyl)ethoxy)phenyl)methyl)-, monohydrochloride, (+-)- ; (+-)-5-(p-(2-(5-Ethyl-2-pyridyl)ethoxy)benzyl)-2,4-thiazolidinedione monohydrochloride ; Pioglitazone hydrochloride ; Actos . It is colourless prisms.

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