Basic information Safety Supplier Related

Febuxostat Impurity 7

Basic information Safety Supplier Related

Febuxostat Impurity 7 Basic information

Product Name:
Febuxostat Impurity 7
Synonyms:
  • Febuxostat Impurity 24/(Z)-2-(3-((hydroxyimino)methyl)-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid
  • Febuxostat-17
  • Febuxostat Impurity 7
  • (Z)-2-(3-((hydroxyimino)methyl)-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid
  • Febuxostat Impurity M
  • 3-Descyano-3-((hydroxyimino)methyl) Febuxostat
  • Febuxostat Impurity 7 (F)
  • 2-(3-((Hydroxyimino)methyl)-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylicacid
CAS:
1350352-70-3
MF:
C16H18N2O4S
MW:
334.39
Mol File:
1350352-70-3.mol
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Febuxostat Impurity 7 Chemical Properties

Melting point:
>215°C (dec.)
storage temp. 
-20°C Freezer
solubility 
DMSO (Slightly)
form 
Solid
color 
White
InChI
InChI=1S/C16H18N2O4S/c1-9(2)8-22-13-5-4-11(6-12(13)7-17-21)15-18-10(3)14(23-15)16(19)20/h4-7,9,21H,8H2,1-3H3,(H,19,20)
InChIKey
MDMGIABSBHFMNF-UHFFFAOYSA-N
SMILES
S1C(C(O)=O)=C(C)N=C1C1=CC=C(OCC(C)C)C(C=NO)=C1
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Febuxostat Impurity 7 Usage And Synthesis

Uses

3-Descyano-3-((hydroxyimino)methyl) Febuxostat is an impurity of Febuxostat (F229000), a xanthine oxidase/xanthine dehydrogenase inhibitor that is used for treating hyperuricemia and chronic gout.

Synthesis

Preparation of 2-[3-((hydroxyimino)methyl)-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid (febuxostat impurity 7) Compound: to pre-cooled sodium hydroxide was added ethyl 2-[3-((hydroxyimino)methyl)-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylate (100 g) in methanol (500 mL) solution solution (22.10 g in 500 mL of water). The reaction mixture was heated to 75 C and stirred at the same temperature for 30 minutes. Water (5 g) was added to the reaction mixture and the reaction mixture was cooled to 25 C. Methanol (100 ml) and water (100 ml) were added to the reaction mixture. The pH was adjusted to 2.0-3.0 using aqueous hydrochloric acid. the reaction mixture was stirred for 5 hours. Filter the precipitated solid and wash with methanol and water. Dry the resulting material. Tetrahydrofuran (270 ml) and carbon (2.25 gms) were added to the resulting material. The reaction mixture was stirred for 30 min and filtered through hyflow. The solvent was completely distilled from the filtrate. Methanol (450 ml) was added to the resulting compound and stirred at 60C for 30 min. The reaction mixture was cooled to 25C and stirred for 2 hours. The precipitated solid was filtered and the substance was dried to give the pure title compound febuxostat impurity 7. Yield: 70 g.

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