Esonarimod

Base Information

• Chemical Name: Esonarimod
• CAS No.: 101973-77-7
• Molecular Formula: C14H16 O4 S
• Molecular Weight: 280.345
• UNII: PF4079THQO
• DSSTox Substance ID: DTXSID9048805
• Nikkaji Number: J472.158F
• Wikidata: Q27286514
• NCI Thesaurus Code: C65540
• ChEMBL ID: CHEMBL2003782
• Mol file: 101973-77-7.mol

Synonyms:2-acetylthiomethyl-3-(4-methylbenzoyl)propionic acid;esonarimod;KE 298;KE-298

Chemical Property of Esonarimod

Chemical Property:

• Vapor Pressure: 6.18E-10mmHg at 25°C
• Boiling Point: 477.7°Cat760mmHg
• Flash Point: 242.7°C
• PSA: 96.74000
• Density: 1.241g/cm³
• LogP: 2.54830
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 280.07693016
• Heavy Atom Count: 19
• Complexity: 345

Purity/Quality:

99.3% ^*data from raw suppliers

Esonarimod ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(=O)CC(CSC(=O)C)C(=O)O
• Uses: Esonarimod, is an antirheumatic drug.

Technology Process of Esonarimod

There total 4 articles about Esonarimod 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: 74.0%

2-methylene-4-(4-methylphenyl)-4-oxobutanoic acid (19340-33-1) + tiolacetic acid (507-09-5) → Esonarimod (101973-77-7)

Guidance literature:

With triethylamine; In toluene; at 60 ℃; for 4h;

DOI:10.1248/cpb.50.1407

Reference yield:

itaconic acid anhydride (2170-03-8) → Esonarimod (101973-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 68.4 percent / AlCl₃ / nitrobenzene / 2 h / 50 °C

2: 74 percent / H₂O; Et₃N / toluene / 4 h / 60 °C

With aluminium trichloride; water; triethylamine; In nitrobenzene; toluene;

DOI:10.1081/SCC-120021986

Reference yield:

toluene (108-88-3,15644-74-3,16713-13-6) → Esonarimod (101973-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 68.4 percent / AlCl₃ / nitrobenzene / 2 h / 50 °C

2: 74 percent / H₂O; Et₃N / toluene / 4 h / 60 °C

With aluminium trichloride; water; triethylamine; In nitrobenzene; toluene;

DOI:10.1081/SCC-120021986

upstream raw materials:

2-methylene-4-(4-methylphenyl)-4-oxobutanoic acid

tiolacetic acid

itaconic acid anhydride

toluene

Downstream raw materials:

(S)-Esonarimod

(R)-Esonarimod

S-methyl-Esonarimod

methyl 5-(4-methylphenyl)-2,3-dihydrothiophene-3-carboxylate