Pyrazinecarboxylic acid, 5-fluoro-, methyl ester (9CI)

Base Information

• Chemical Name: Pyrazinecarboxylic acid, 5-fluoro-, methyl ester (9CI)
• CAS No.: 169335-35-7
• Molecular Formula: C₆H₅FN₂O₂
• Molecular Weight: 156.116
• Mol file: 169335-35-7.mol

Synonyms:Pyrazinecarboxylicacid, 5-fluoro-, methyl ester (9CI)

Chemical Property of Pyrazinecarboxylic acid, 5-fluoro-, methyl ester (9CI)

Chemical Property:

• Boiling Point: 220.1±35.0 °C(Predicted)
• PKA: -4.25±0.10(Predicted)
• PSA: 52.08000
• Density: 1.323±0.06 g/cm3(Predicted)
• LogP: 0.40230

Purity/Quality:

methyl5-fluoropyrazine-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Pyrazinecarboxylic acid, 5-fluoro-, methyl ester (9CI)

There total 2 articles about Pyrazinecarboxylic acid, 5-fluoro-, methyl ester (9CI) 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: 66.0%

methyl 5-chloropyrazine-2-carboxylate (33332-25-1) → 5-fluoro-pyrazine-2-carboxylic acid methyl ester (169335-35-7)

Guidance literature:

With silver fluoride; In acetonitrile; Heating / reflux;

Reference yield:

5-chloropyrazine-2-carbonyl chloride (88625-23-4) → 5-fluoro-pyrazine-2-carboxylic acid methyl ester (169335-35-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / 48 h / Ambient temperature

2: AgF / acetonitrile / 48 h / Heating

With pyridine; silver fluoride; In dichloromethane; acetonitrile;

DOI:10.1021/jm00020a003

Reference yield:

5-fluoro-pyrazine-2-carboxylic acid methyl ester (169335-35-7) → 5-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazine-2-carboxylic acid methyl ester (1427744-12-4)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonia / tetrahydrofuran / -78 - 20 °C / Inert atmosphere; Sealed tube

2: Inert atmosphere

With ammonia; In tetrahydrofuran;

DOI:10.1021/ml400027y

upstream raw materials:

methyl 5-chloropyrazine-2-carboxylate

5-chloropyrazine-2-carbonyl chloride

Downstream raw materials:

5-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazine-2-carboxylic acid methyl ester

2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-hydroxymethyl-pyrazin-2-yl)propionamide

2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-methanesulfonylmethyl-pyrazin-2-yl)-propionamide

Refernces

• 1、 Qian, Yimin,Corbett, Wendy L.,Berthel, Steven J.,Choi, Duk Soon,Dvorozniak, Mark T.,Geng, Wanping,Gillespie, Paul,Guertin, Kevin R.,Haynes, Nancy-Ellen,Kester, Robert F.,Mennona, Francis A.,Moore, David,Racha, Jagdish,Radinov, Roumen,Sarabu, Ramakanth,Scott, Nathan R.,Grimsby, Joseph,Mallalieu, Navita L.. "Identification of RO4597014, a glucokinase activator studied in the clinic for the treatment of type 2 diabetes". supporting information. p. 414 - 418. Retrieved 2013/07/25.