Febuxostat Impurity 6

Base Information

• Chemical Name: Febuxostat Impurity 6
• CAS No.: 1271738-74-9
• Molecular Formula: C₁₈H₂₂N₂O₄S
• Molecular Weight: 362.45
• Mol file: 1271738-74-9.mol

Synonyms:ethyl 2-[3-((hydroxyimino)methyl)-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylate

Chemical Property of Febuxostat Impurity 6

Chemical Property:

• Melting Point: >125°C (dec.)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2-[3-[(Hydroxyimino)methyl]-4-(2-methylpropoxy)phenyl]-4-methyl-5-Thiazolecarboxylic Acid Ethyl Ester, is an impurity of Febuxostat (F229000), an 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 Febuxostat Impurity 6

There total 3 articles about Febuxostat Impurity 6 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: 73.0%

Isobutyl bromide (78-77-3) + ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate (161798-01-2) → ethyl 2-[3-((hydroxyimino)methyl)-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylate (1271738-74-9)

Guidance literature:

Isobutyl bromide; ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate; With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 70 ℃; for 4h;

With hydroxylamine hydrochloride; In N,N-dimethyl-formamide; at 70 ℃; for 7h;

Reference yield:

2-(3-formyl-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester (161798-03-4) → ethyl 2-[3-((hydroxyimino)methyl)-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylate (1271738-74-9)

Guidance literature:

With hydroxylamine hydrochloride; In methanol; at 65 ℃;

Reference yield:

ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate (161798-01-2) → ethyl 2-[3-((hydroxyimino)methyl)-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylate (1271738-74-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 70 - 75 °C

1.2: 5 h

2.1: hydroxylamine hydrochloride / methanol / 65 °C

With hydroxylamine hydrochloride; potassium carbonate; potassium iodide; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

Isobutyl bromide

ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate

2-(3-formyl-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Downstream raw materials:

febuxostat

2-[3-((hydroxyimino)methyl)-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid

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