Tetomilast

Base Information

• Chemical Name: Tetomilast
• CAS No.: 145739-56-6
• Molecular Formula: C19H18 N2 O4 S
• Molecular Weight: 370.429
• Hs Code.: 2934100090
• UNII: S6RXB5KF56
• DSSTox Substance ID: DTXSID00163149
• Nikkaji Number: J634.529H
• Wikidata: Q27095582
• NCI Thesaurus Code: C90922
• Pharos Ligand ID: T7HFRLMADXCB
• Metabolomics Workbench ID: 149443
• ChEMBL ID: CHEMBL332750
• Mol file: 145739-56-6.mol

Synonyms:6-(2-(3,4-diethoxyphenyl)thiazol-4-yl)-pyridine-2-carboxylic acid;OPC 6535;OPC-6535;OPC6535;tetomilast

Chemical Property of Tetomilast

Chemical Property:

• Vapor Pressure: 3.53E-15mmHg at 25°C
• Boiling Point: 598.6°Cat760mmHg
• PKA: 3.28±0.10(Predicted)
• Flash Point: 315.8°C
• PSA: 109.78000
• Density: 1.279g/cm³
• LogP: 4.36770
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 370.09872823
• Heavy Atom Count: 26
• Complexity: 467

Purity/Quality:

99%, ^*data from raw suppliers

6-(2-(3,4-Diethoxyphenyl)thiazol-4-yl)picolinicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC1=C(C=C(C=C1)C2=NC(=CS2)C3=NC(=CC=C3)C(=O)O)OCC
• Recent ClinicalTrials: A Dose-finding Study of OPC-6535 in Patients With Active Ulcerative Colitis
• Recent EU Clinical Trials: A Phase 3, Multi-center, Randomized, Double-blind, Placebo-controlled, Parallel-arm Study of the Efficacy and Safety of OPC-6535 Tablets in the Treatment of Subjects with Active Ulcerative Colitis

Technology Process of Tetomilast

There total 8 articles about Tetomilast 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: 93.0%

→ 6-[2-(3,4-diethoxyphenyl)-thiazole-4-yl]pyridine-2-carboxylic acid (145739-56-6)

Guidance literature:

Purification / work up;

Reference yield: 91.3%

methyl 6-<2-(3,4-diethoxyphenyl)thiazol-4-yl>pyridine-2-carboxylate (160322-91-8) → 6-[2-(3,4-diethoxyphenyl)-thiazole-4-yl]pyridine-2-carboxylic acid (145739-56-6)

Guidance literature:

With sodium hydroxide; In ethanol; for 4h; Heating;

DOI:10.1021/jm00002a017

Reference yield: 78.4%

2-(2-chloroacetyl)-6-pyridine carboxylic acid (298692-34-9) + 3,4-diethoxybenzthioamide (60759-00-4) → 6-[2-(3,4-diethoxyphenyl)-thiazole-4-yl]pyridine-2-carboxylic acid (145739-56-6)

Guidance literature:

2-(2-chloroacetyl)-6-pyridine carboxylic acid; 3,4-diethoxybenzthioamide; In 1,2-dimethoxyethane; water; for 2h; Heating / reflux;

With potassium hydroxide; In water; Product distribution / selectivity;

upstream raw materials:

methyl 6-<2-(3,4-diethoxyphenyl)thiazol-4-yl>pyridine-2-carboxylate

2-(2-chloroacetyl)-6-pyridine carboxylic acid

3,4-diethoxybenzthioamide

3,4-diethoxybenzonitrile

Refernces

• 1、 Chihiro,Nagamoto,Takemura,Kitano,Komatsu,Sekiguchi,Tabusa,Mori,Tominaga,Yabuuchi. "Novel thiazole derivatives as inhibitors of superoxide production by human neutrophils: Synthesis and structure-activity relationships". . p. 353 - 358. Retrieved 2007/10/02.