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

Base Information

• Chemical Name: Methyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate
• CAS No.: 923942-34-1
• Molecular Formula: C₁₇H₁₈N₂O₃S
• Molecular Weight: 330.408
• Mol file: 923942-34-1.mol

Synonyms:methyl 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate;

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

Chemical Property:

• Melting Point: 157-159°C
• Boiling Point: 486.8±55.0 °C(Predicted)
• PKA: 0.95±0.10(Predicted)
• PSA: 100.45000
• Density: 1.24
• LogP: 3.81158
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

Methyl2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylate is a 4-Methylthiazole-5-carboxylic Acid derivative as a potential inhibitor of mucin onco proteins for breast cancer therapy.Also, it is derived from Febuxostat (F229000), which is a xanthine oxidase/xanthine dehydrogenase inhibitor and 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 Methyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate

There total 7 articles about Methyl 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: 98.0%

methanol (67-56-1) + 2-[3-cyano-4-isobutyloxyphenyl]-4-methylthiazole-5-carboxylic acid chloride → methyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate (923942-34-1)

Guidance literature:

With triethylamine; In toluene; at 70 - 75 ℃; for 0.166667h;

DOI:10.1016/j.bmcl.2014.07.058

Reference yield: 87.0%

methyl chloroacetate (96-34-4) + 3-cyanoisobutoxybenzothioamide (163597-57-7) → methyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate (923942-34-1)

Guidance literature:

In ethanol; at 100 ℃; for 2h;

Reference yield:

4-cyanophenol (767-00-0) → methyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate (923942-34-1)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium iodide / N,N-dimethyl-formamide / 10 h / 60 °C

2: hydrogenchloride / N,N-dimethyl-formamide / 4 h / 80 °C

3: hexamethylenetetramine / 10 h / 75 °C

4: hydroxylamine hydrochloride; sodium acetate; formic acid / 5 h / Reflux

5: ethanol / 2 h / 100 °C

With hydrogenchloride; formic acid; hexamethylenetetramine; hydroxylamine hydrochloride; sodium acetate; potassium iodide; In ethanol; N,N-dimethyl-formamide;

upstream raw materials:

febuxostat

methanol

methyl chloroacetate

3-cyanoisobutoxybenzothioamide

Refernces

• 1、 Kilaru, Ravendra Babu,Valasani, Koteswara Rao,Yellapu, Nanda Kumar,Osuru, Hari Prasad,Kuruva, Chandra Sekhar,Matcha, Bhaskar,Chamarthi, Naga Raju. "Design, synthesis, in silico and in vitro studies of novel 4-methylthiazole-5-carboxylic acid derivatives as potent anti-cancer agents". . p. 4580 - 4585. Retrieved 2015/02/19.