3-Amino-6-methylthieno[2,3-b]pyridine-2-carboxylic acid

Base Information

• Chemical Name: 3-Amino-6-methylthieno[2,3-b]pyridine-2-carboxylic acid
• CAS No.: 59488-60-7
• Molecular Formula: C₉H₈N₂O₂S
• Molecular Weight: 208.241
• Hs Code.: 29335990
• European Community (EC) Number: 672-257-2
• Mol file: 59488-60-7.mol

Synonyms:3-amino-6-methylthieno[2,3-b]pyridine-2-carboxylic acid;59488-60-7;Methylmercury(ii)chloride;Cambridge id 7196545;SCHEMBL19212039;STK332605;AKOS001676681;AT10593;CCG-112729;BB 0254778;CS-0084896;EU-0012738;FT-0645314;EN300-227049;A832339;SR-01000500706;J-511676;SR-01000500706-1;3-amino-6-methylthieno[2,3-b]pyridine-2-carboxylicacid;3-amino-6-methyl-2-thieno[2,3-b]pyridinecarboxylic acid;3-azanyl-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid

Chemical Property of 3-Amino-6-methylthieno[2,3-b]pyridine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.59E-08mmHg at 25°C
• Refractive Index: 1.76
• Boiling Point: 440.2 °C at 760 mmHg
• Flash Point: 220 °C
• PSA: 104.45000
• Density: 1.516 g/cm³
• LogP: 2.46630
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 208.03064868
• Heavy Atom Count: 14
• Complexity: 249

Purity/Quality:

99.5% ^*data from raw suppliers

3-Amino-6-methylthieno[2,3-b]pyridine-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC2=C(C=C1)C(=C(S2)C(=O)O)N

Technology Process of 3-Amino-6-methylthieno[2,3-b]pyridine-2-carboxylic acid

There total 4 articles about 3-Amino-6-methylthieno[2,3-b]pyridine-2-carboxylic acid 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: 80.0%

ethyl 3-amino-6-methylthieno[2,3-b]pyridine-2-carboxylate (52505-51-8) → 3-amino-6-methylthieno[2,3-b]pyridine-2-carboxylic acid (59488-60-7)

Guidance literature:

With sodium hydroxide; In ethanol; at 70 ℃; for 6h; Inert atmosphere;

DOI:10.1039/c8ob02753f

Reference yield:

2,6-dichloro-3-pyridinecarbonitrile (40381-90-6) → 3-amino-6-methylthieno[2,3-b]pyridine-2-carboxylic acid (59488-60-7)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hydroxide / N,N-dimethyl-formamide; water / 1.5 h / 0 °C / Inert atmosphere

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; caesium carbonate / N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere

3: sodium hydroxide / ethanol / 6 h / 70 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; caesium carbonate; potassium hydroxide; sodium hydroxide; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1039/c8ob02753f

Reference yield:

ethyl 3-amino-6-chlorothieno[2,3-b]pyridine-2-carboxylate → 3-amino-6-methylthieno[2,3-b]pyridine-2-carboxylic acid (59488-60-7)

Guidance literature:

Multi-step reaction with 2 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; caesium carbonate / N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere

2: sodium hydroxide / ethanol / 6 h / 70 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; caesium carbonate; sodium hydroxide; In ethanol; N,N-dimethyl-formamide;

DOI:10.1039/c8ob02753f

upstream raw materials:

2-chloro-6-methylnicotinonitrile

ethyl 3-amino-6-methylthieno[2,3-b]pyridine-2-carboxylate

2,6-dichloro-3-pyridinecarbonitrile

Refernces

• 1、 -. "THIENOPYRIDINE CARBOXAMIDES AS UBIQUITIN-SPECIFIC PROTEASE INHIBITORS". . . Retrieved 2017/09/05.