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ChemicalBook--->CAS DataBase List--->160844-75-7

160844-75-7

160844-75-7 Structure

160844-75-7 Structure
IdentificationMore
[Name]

Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate
[CAS]

160844-75-7
[Synonyms]

Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate
[EINECS(EC#)]

927-913-5
[Molecular Formula]

C18H20N2O3S
[MDL Number]

MFCD09833701
[Molecular Weight]

344.43
[MOL File]

160844-75-7.mol
Chemical PropertiesBack Directory
[Melting point ]

176 °C
[Boiling point ]

497.1±55.0 °C(Predicted)
[density ]

1.22
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

DMSO (Slightly, Heated), Methanol (Very Slightly, Heated)
[form ]

Solid
[pka]

1.02±0.10(Predicted)
[color ]

White to Off-White
[InChI]

InChI=1S/C18H20N2O3S/c1-5-22-18(21)16-12(4)20-17(24-16)13-6-7-15(14(8-13)9-19)23-10-11(2)3/h6-8,11H,5,10H2,1-4H3
[InChIKey]

OGAZOYHQFBSRMC-UHFFFAOYSA-N
[SMILES]

S1C(C(OCC)=O)=C(C)N=C1C1=CC=C(OCC(C)C)C(C#N)=C1
[CAS DataBase Reference]

160844-75-7(CAS DataBase Reference)
Safety DataBack Directory
[HS Code ]

2934.10.2000
Raw materials And Preparation ProductsBack Directory
[Raw materials]

5-iodo-2-isobutoxybenzonitrile-->ETHYL 2-(3-FORMYL-4-ISOBUTOXYPHENYL)-4-METHYLTHIAZOLE-5-CARBOXYLATE-->Ethyl 2-(3-Formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate-->Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate-->Ethyl 2-(3-bromo-4-isobutoxyphenyl)- 4-methyl-5-thiazolecarboxylate-->5-bromo-2-isobutoxy benzonitirle-->3-Cyano-4-(2-methylpropoxy)benzenecarbothioamide-->(3-cyano-4-isobutoxyphenyl)boronic acid-->Febuxostat Impurity 6-->ETHYL 2-BROMO-4-METHYL-1,3-THIAZOLE-5-CARBOXYLATE-->Ethyl 4-methyl-5-thiazoleactate-->Ethyl 2-(3-Cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate-->5-Bromo-2-fluorobenzonitrile-->1-Bromo-2-methylpropane
[Preparation Products]

Febuxostat
Hazard InformationBack Directory
[Chemical Properties]

White crystalline powder
[Uses]

Ethyl 2-(3-Cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate is an impurity of Febuxostat (F229000), a xanthine oxidase/xanthine dehydrogenase inhibitor. Used for treatment of hyperuricemia and chronic gout. 40-120 mg/day febuxostat was proven effective in lowering serum urate levels when administered to manage hyperuricemia in patients with gout.
[Synthesis]

CarboxylatePotassium carbonate (300 g, 2.17 mol) and isobutyl bromide (142.7 g, 1.041 mol) were added to a solution of ethyl-2-(3-cyano-4-hydroxyphenyl)-4-methyl-5-thiazole carboxylate (100 g, 0.347 mol) in dimethylformamide (300 mL), and the reaction mixture was heated at a temperature of about 75°C for about 8 hours. After completion of the reaction, the reaction mixture was cooled to about 40°C, and water was added. The reaction mixture was further cooled to about 0°C and stirred for about 1 hour. The solid thus obtained was filtered, washed with water, and dried to give Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate. (Yield: 11 lg, 92.9%) Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate
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