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

Base Information

• Chemical Name: Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate
• CAS No.: 160844-75-7
• Molecular Formula: C18H20N2O3S
• Molecular Weight: 344.434
• Hs Code.: 2942000000
• European Community (EC) Number: 927-913-5
• DSSTox Substance ID: DTXSID901144416
• Nikkaji Number: J2.523.897D
• Mol file: 160844-75-7.mol

Synonyms:160844-75-7;Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate;ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate;Ethyl 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate;Ethyl2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate;EC 927-913-5;5-Thiazolecarboxylic acid, 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-, ethyl ester;2-(3-Cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester;5-Thiazolecarboxylic acid, 2-(3-cyano-4-(2-methylpropoxy)phenyl)-4-methyl-, ethyl ester;Febuxostat Ethyl Ester;SCHEMBL31601;DTXSID901144416;BCP23118;MFCD09833701;AKOS005145711;Ethyl 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylate;AC-5911;DS-13004;A3563;AM20090759;CS-0151841;E1414;FT-0653024;A24932;A851007;Q-103511;Ethyl 2-(3-Cyano-4-Isobutoxy Phenyl)-4-Methylthiazole-5-Carboxylate;ethyl 2-[3-cyano-4-(2-methyl propoxy)phenyl]-4-methyl-5-thiazolcarboxylate;Ethyl-2-(3-Cyano-4-Isobutyloxyphenyl)-4-Methyl-5-Thiazole Carboxylate;2-(3-cyano-4-isobutoxy-phenyl)-4-methylthiazole-5-carboxylic acid ethyl ester;2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylic Acid Ethyl Ester;Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate;Febuxostat Ethyl Ester (2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylic Acid Ethyl Ester);Febuxostat Ethyl Ester (2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylic Acid Ethyl Ester)

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 176 °C
• Refractive Index: 1.57
• Boiling Point: 497.149 °C at 760 mmHg
• PKA: 1.02±0.10(Predicted)
• Flash Point: 254.467 °C
• PSA: 100.45000
• Density: 1.22 g/cm³
• LogP: 4.20168
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly, Heated), Methanol (Very Slightly, Heated)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 344.11946368
• Heavy Atom Count: 24
• Complexity: 476

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 2-(3-Cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1=C(N=C(S1)C2=CC(=C(C=C2)OCC(C)C)C#N)C
• 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.

Technology Process of Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate

There total 49 articles about Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate 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: 100.0%

5-bromo-2-isobutoxy-benzonitrile (876918-26-2) + ethyl 4-methylthiazole-5-carboxylate (20582-55-2) → C22H24N2O2 (1240593-43-4) + diethyl 4,4?-dimethyl-2,2?-bithiazole-5,5?-dicarboxylate (3944-31-8) + 2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester (160844-75-7)

Guidance literature:

With di-tert-butyl(cyclohexyl)phosphine; potassium carbonate; palladium dichloride; In 5,5-dimethyl-1,3-cyclohexadiene; at 140 ℃; for 24h; Reagent/catalyst; Inert atmosphere;

Reference yield: 98.5%

2-(3-bromo-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester (144060-96-8) + copper(l) cyanide → 2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester (160844-75-7)

Guidance literature:

With copper(l) iodide; In N,N-dimethyl-formamide; at 130 - 140 ℃; for 16h;

Reference yield: 98.2%

Isobutyl bromide (78-77-3) + ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate (161798-02-3) → 2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester (160844-75-7)

Guidance literature:

With potassium carbonate; potassium iodide; In ethyl acetate; at 65 - 70 ℃; for 5h; Temperature; Solvent; Reagent/catalyst;

upstream raw materials:

ethyl 2-chloro-3-oxo-butyrate

3-cyanoisobutoxybenzothioamide

4-isobutoxyisophthalonitrile

4-nitrobenzonitrile

Downstream raw materials:

febuxostat

2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid methylamine

2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid tert-butylamine

Refernces

• 1、 Rashad, Aya Y.,Kassab, Shaymaa E.,Daabees, Hoda G.,Abdel Moneim, Ahmed E.,Rostom, Sherif A.F.. "Febuxostat-based amides and some derived heterocycles targeting xanthine oxidase and COX inhibition. Synthesis, in vitro and in vivo biological evaluation, molecular modeling and in silico ADMET studies". . . Retrieved 2021.
• 2、 -. "Improved method for synthesizing febuxostat key intermediate". Paragraph 0022-0023. . Retrieved 2021/01/15.