Febuxostat (67m-4)

Base Information

• Chemical Name: Febuxostat (67m-4)
• CAS No.: 407582-49-4
• Molecular Formula: C16H14N2O5S
• Molecular Weight: 346.35800
• UNII: NRN27Y63ZG
• DSSTox Substance ID: DTXSID701148050
• Nikkaji Number: J3.359.914E
• Wikidata: Q27285015
• Mol file: 407582-49-4.mol

Synonyms:Febuxostat (67m-4);407582-49-4;UNII-NRN27Y63ZG;NRN27Y63ZG;5-Thiazolecarboxylic acid, 2-(4-(2-carboxypropoxy)-3-cyanophenyl)-4-methyl-;67M-4;2-[4-(2-carboxypropoxy)-3-cyanophenyl]-4-methyl-1,3-thiazole-5-carboxylic acid;2-(4-(2-carboxypropoxy)-3-cyanophenyl)-4-methyl-5-thiazolecarboxylic acid;Febuxostat 67M-4;2-[4-(2-carboxypropoxy)-3-cyanophenyl]-4-methyl-5-thiazolecarboxylic acid;SCHEMBL437353;DTXSID701148050;FEBUXOSTAT METABOLITE 67M-4;Q27285015;2-[3-Cyano-4-(2-carboxypropoxy)phenyl]-4-methylthiazole-5-carboxylic acid

Chemical Property of Febuxostat (67m-4)

Chemical Property:

• PSA: 148.75000
• LogP: 2.78788
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 346.06234272
• Heavy Atom Count: 24
• Complexity: 534

Purity/Quality:

99% ^*data from raw suppliers

Febuxostat67M-4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(SC(=N1)C2=CC(=C(C=C2)OCC(C)C(=O)O)C#N)C(=O)O
• Uses: Febuxostat 67M-4 is a derivative compound of Febuxostat 67M-1 (F229005) which is an inhibitor of xanthine oxidase. It reduces uric acid production in the body and also used to reduce the risk of gout or kidney stone formation.

Technology Process of Febuxostat (67m-4)

There total 7 articles about Febuxostat (67m-4) 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: 89.0%

3-{2-cyano-4-[5-(ethoxycarbonyl)-4-methylthiazol-2-yl]phenoxy}-2-methylpropanoic acid → 2-[4-(2-carboxypropoxy)-3-cyanophenyl]-4-methylthiazole-5-carboxylic acid (407582-49-4)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; ethanol; at 60 ℃; for 1.5h;

DOI:10.2174/1570178612666150108000805

Reference yield:

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate (161798-02-3) → 2-[4-(2-carboxypropoxy)-3-cyanophenyl]-4-methylthiazole-5-carboxylic acid (407582-49-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 80 °C

1.2: 4 h / 80 °C

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium chlorite / water; acetonitrile; aq. phosphate buffer / 6 h / 35 °C / pH 6.7

3.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 1.5 h / 60 °C

With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; water; potassium carbonate; potassium iodide; sodium hydroxide; In tetrahydrofuran; aq. phosphate buffer; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.2174/1570178612666150108000805

Reference yield:

4-hydroxythiobenzamide (25984-63-8) → 2-[4-(2-carboxypropoxy)-3-cyanophenyl]-4-methylthiazole-5-carboxylic acid (407582-49-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: ethanol / Reflux

2.1: phosphorus pentoxide

3.1: hydroxylamine hydrochloride; sodium acetate; formic acid

4.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 80 °C

4.2: 4 h / 80 °C

5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium chlorite / water; acetonitrile; aq. phosphate buffer / 6 h / 35 °C / pH 6.7

6.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 1.5 h / 60 °C

With sodium hypochlorite; sodium chlorite; formic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; phosphorus pentoxide; hydroxylamine hydrochloride; water; sodium acetate; potassium carbonate; potassium iodide; sodium hydroxide; In tetrahydrofuran; aq. phosphate buffer; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.2174/1570178612666150108000805

upstream raw materials:

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

4-hydroxythiobenzamide

(2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester)

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

Refernces