Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate Chemical Properties

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 Information

HS Code 

2934.10.2000

Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate Usage And Synthesis

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(160844-75-7)Related Product Information

• Memantine
• Ethyl 2-(3-Cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate
• ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate
• Febuxostat Acyl-β-D-glucuronide
• Febuxostat Descyano Impurity
• isopropyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate
• Febuxostat Impurity 6
• 2,2'-[4-(2-Methylpropoxy)-1,3-phenylene]bis[4-Methyl-5-thiazolecarboxylic Acid
• 2-[3-Carboxy-4-(2-Methylpropoxy)phenyl]-4-Methyl-5-thiazolecarboxylic Acid
• 2-(3-cyano-4-propoxyphenyl)-4-methylthiazole-5-carboxylic acid
• Febuxostat Impurity 8
• 4-(2-Methylpropoxy)-1,3-benzenedicarbothioaMide
• Febuxostat
• ETHYL 2-(3-FORMYL-4-ISOBUTOXYPHENYL)-4-METHYLTHIAZOLE-5-CARBOXYLATE
• ethyl 2-(4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate
• 3-Cyano-4-isobutoxybenzoic acid
• FeBuxostat Impurity 33
• Febuxostat impurity 37