Ethyl 5-cyano-1,6-dihydro-2-methyl-6-oxo-3-pyridinecarboxylate

Base Information

• Chemical Name: Ethyl 5-cyano-1,6-dihydro-2-methyl-6-oxo-3-pyridinecarboxylate
• CAS No.: 52600-52-9
• Molecular Formula: C10H10 N2 O3
• Molecular Weight: 206.201
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID80200581
• Nikkaji Number: J438.391E
• ChEMBL ID: CHEMBL1275980
• Mol file: 52600-52-9.mol

Synonyms:ethyl 5-cyano-1,6-dihydro-2-methyl-6-oxo-3-pyridinecarboxylate;ethyl CDMOP

Chemical Property of Ethyl 5-cyano-1,6-dihydro-2-methyl-6-oxo-3-pyridinecarboxylate

Chemical Property:

• Vapor Pressure: 1.02E-05mmHg at 25°C
• Boiling Point: 371.6°Cat760mmHg
• Flash Point: 178.6°C
• PSA: 83.21000
• Density: 1.26g/cm³
• LogP: 1.14398
• Storage Temp.: 2-8°C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 206.06914219
• Heavy Atom Count: 15
• Complexity: 423

Purity/Quality:

98%Min ^*data from raw suppliers

Ethyl 5-cyano-6-hydroxy-2-methylnicotinate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(NC(=O)C(=C1)C#N)C

Technology Process of Ethyl 5-cyano-1,6-dihydro-2-methyl-6-oxo-3-pyridinecarboxylate

There total 17 articles about Ethyl 5-cyano-1,6-dihydro-2-methyl-6-oxo-3-pyridinecarboxylate 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%

ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate (134653-70-6,51145-57-4) → 5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester (52600-52-9)

Guidance literature:

cyanoacetic acid amide; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 2h;

ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate; In tetrahydrofuran; at 20 ℃; for 16h;

Reference yield: 93.0%

ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate (134653-70-6,51145-57-4) + cyanoacetic acid amide (107-91-5) → 5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester (52600-52-9)

Guidance literature:

cyanoacetic acid amide; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 2h;

ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate; In tetrahydrofuran; at 20 ℃; for 16h;

Reference yield: 86.0%

ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate (134653-70-6,51145-57-4) + malononitrile (109-77-3) → 5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester (52600-52-9)

Guidance literature:

ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate; malononitrile; With sodium ethanolate; In ethanol; at 20 ℃;

With acetic acid;

DOI:10.1021/op200368m

upstream raw materials:

ethyl 2-cyanoacetate

2-ethoxymethylene-3-oxobutanoic acid ethyl ester

sodium acetylamide

ammonia

Downstream raw materials:

ethyl 6-chloro-5-cyano-2-methylnicotinate

5-cyano-2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid phenylamide

1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile

ethyl 6-{4-[(benzylsulfonyl)carbamoyl]-piperidin-1-yl}-5-cyano-2-methylpyridine-3-carboxylate

Refernces

• 1、 -. "MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS". Paragraph 00982. . Retrieved 2018/09/12.
• 2、 Andersen, Soren M.,Aurell, Carl-Johan,Zetterberg, Fredrik,Bollmark, Martin,Ehrl, Robert,Schuisky, Peter,Witt, Anette. "Development of a Multi-Kilogram-Scale Synthesis of AZD1283: A Selective and Reversible Antagonist of the P2Y12 Receptor". supporting information. p. 1543 - 1551. Retrieved 2014/01/06.