ETHYL 2-(3-FORMYL-4-ISOBUTOXYPHENYL)-4-METHYLTHIAZOLE-5-CARBOXYLATE Chemical Properties

Melting point:

158-160°C

Boiling point:

495.9±55.0 °C(Predicted)

Density 

1.183

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly, Sonicated)

form 

Solid

pka

1.39±0.10(Predicted)

color 

Pale Yellow

InChI

InChI=1S/C18H21NO4S/c1-5-22-18(21)16-12(4)19-17(24-16)13-6-7-15(14(8-13)9-20)23-10-11(2)3/h6-9,11H,5,10H2,1-4H3

InChIKey

AIQMFFCWDAIGNV-UHFFFAOYSA-N

SMILES

S1C(C(OCC)=O)=C(C)N=C1C1=CC=C(OCC(C)C)C(C=O)=C1

CAS DataBase Reference

161798-03-4(CAS DataBase Reference)

ETHYL 2-(3-FORMYL-4-ISOBUTOXYPHENYL)-4-METHYLTHIAZOLE-5-CARBOXYLATE Usage And Synthesis

Uses

Ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate is an impurity of Febuxostat (F229000), which is a xanthine oxidase/xanthine dehydrogenase inhibitor, used for treatment of hyperuricemia and chronic gout.

Synthesis

Preparation of Compound of formula III)[0094] A compound of formula II (10.0 gr, 34.33 mmol) was reacted with iso- butyl bromide (18.9 gr, 137.3 mmol) in the presence of potassium carbonate (19.0 gr, 137.3 mmol) and potassium iodide (2.3 gr, 13.7 mmol) in 60 ml dimethylformamide. The reaction was performed at about 70°C during 4 hours. The reaction mixture was extracted at 70°C using 300 ml ethyl acetate and 600 ml water. The separated aqueous phase was washed twice with 100 ml ethyl acetate. The combined organic phase was washed twice with 100 ml water and then concentrated to dryness. The resulting solid residue was re- crystallized from 70 ml ethyl acetate, filtered and dried under reduced pressure at about 40°C to provide a compound of formula III (8.9 gr, yield - 83percent). The Compound of formula III purity is 99.1percent (by HPLC).

ETHYL 2-(3-FORMYL-4-ISOBUTOXYPHENYL)-4-METHYLTHIAZOLE-5-CARBOXYLATE(161798-03-4)Related Product Information

• Febuxostat
• Ethyl 2-(3-Cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate
• Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate
• isopropyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate
• 2-(3-cyano-4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid
• 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
• 4-HYDROXYTHIOBENZAMIDE
• ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate
• ethyl 2-(4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate
• 3-Cyano-4-isobutoxybenzoic acid
• FeBuxostat Impurity 33
• Febuxostat impurity 37
• Febuxostat-d9