4-(p-Tolylthio)thieno[2,3-c]pyridine-2-carboxamide

Base Information

• Chemical Name: 4-(p-Tolylthio)thieno[2,3-c]pyridine-2-carboxamide
• CAS No.: 251992-66-2
• Molecular Formula: C15H12N2OS2
• Molecular Weight: 300.405
• UNII: TP7TB1SSZD
• DSSTox Substance ID: DTXSID80179864
• Nikkaji Number: J1.525.129H
• Wikidata: Q27195214
• Pharos Ligand ID: 3PAZPSUQGWD2
• ChEMBL ID: CHEMBL267678
• Mol file: 251992-66-2.mol

Synonyms:251992-66-2;A-205804;4-(p-tolylthio)thieno[2,3-c]pyridine-2-carboxamide;A 205804;4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide;UNII-TP7TB1SSZD;TP7TB1SSZD;CHEMBL267678;A205804;4-((4-Methylphenyl)thio)thieno(2,3-C)pyridine-2-carboxamide;4-(4-methylphenyl)sulfanylthieno[2,3-c]pyridine-2-carboxamide;Thieno(2,3-C)pyridine-2-carboxamide, 4-((4-methylphenyl)thio)-;Thieno[2,3-c]pyridine-2-carboxamide, 4-[(4-methylphenyl)thio]-;SCHEMBL7057661;DTXSID80179864;CHEBI:114180;HMS3269O07;HMS3413F09;HMS3651P04;HMS3677F09;BCP06441;BKA99266;EX-A1788;BDBM50098512;MFCD09038566;s2885;AKOS024457147;CCG-267472;NCGC00167761-01;NCGC00167761-02;NCGC00167761-04;AC-33049;AS-71317;HY-100226;CS-0018356;FT-0750798;SW219899-1;T3498;EC-000.2377;D83118;A919378;J-015866;BRD-K77627880-001-01-6;Q27195214;4-p-Tolylsulfanyl-thieno[2,3-c]pyridine-2-carboxylic acid amide;4-[(4-METHYLPHENYL)SULFANYL]THIENO[2,3-C]PYRIDINE-2-CARBOXAMIDE

Chemical Property of 4-(p-Tolylthio)thieno[2,3-c]pyridine-2-carboxamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 198-199℃
• Boiling Point: 581.348°C at 760 mmHg
• PKA: 15.12±0.30(Predicted)
• Flash Point: 305.388°C
• PSA: 109.52000
• Density: 1.406g/cm³
• LogP: 4.55510
• Storage Temp.: Store at +4°C
• Solubility.: ≥30 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 300.03910536
• Heavy Atom Count: 20
• Complexity: 358

Purity/Quality:

99%+, ^*data from raw suppliers

A 205804 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)SC2=C3C=C(SC3=CN=C2)C(=O)N
• Description: A-205804 is a potent inhibitor of E-selectin and ICAM-1 expression in human vascular endothelial cells stimulated with TNF-α (IC50s = 20 and 25 nM, respectively). It does not block expression of VCAM-1 (IC50 > 1,000 nM).
• Uses: 4-[(4-Methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide is a reagent used in the preparation of selective inhibitors of cell adhesion molecule expression in human endothelial cells.

Technology Process of 4-(p-Tolylthio)thieno[2,3-c]pyridine-2-carboxamide

There total 7 articles about 4-(p-Tolylthio)thieno[2,3-c]pyridine-2-carboxamide 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:

4-p-tolylsulfanyl-thieno[2,3-c]pyridine-2-carbonyl chloride → 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide (251992-66-2)

Guidance literature:

With ammonium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/jm000452m

Reference yield:

ammonium hydroxide (1336-21-6) + oxalyl dichloride (79-37-8) + 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxylic acid (251992-65-1) → 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide (251992-66-2)

Guidance literature:

In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

3,5-dichloropyridine (2457-47-8) → 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide (251992-66-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

1.2: 90 percent / tetrahydrofuran / 1.4 h / -78 °C

2.1: K₂CO₃ / dimethylformamide / 1.5 h / 0 - 20 °C

3.1: K₂CO₃ / dimethylformamide / 2 h / 60 °C

4.1: 93 percent / aq. LiOH / propan-2-ol / 1 h / 75 °C

5.1: oxalyl chloride; DMF / CH₂Cl₂ / 0.5 h / 20 °C

6.1: aq. NH₃ / tetrahydrofuran / 0.5 h / 20 °C

With lithium hydroxide; ammonium hydroxide; oxalyl dichloride; potassium carbonate; N,N-dimethyl-formamide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm000452m

upstream raw materials:

3,5-dichloropyridine

3,5-dichloropyridine-4-carboxaldehyde

3-[(4-methylphenyl)thio]-5-chloro-4-pyridinecarboxyaldehyde

4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxylic acid

Refernces

• 1、 -. "Cell adhesion-inhibiting antiinflammatory compounds". . . Retrieved 2008/06/13.