64119-42-2

Basic information

• Product Name: Ethyl 6-chloro-5-cyano-2-methylnicotinate
• Synonyms: Ethyl 6-chloro-5-cyano-2-methylnicotinate;6-CHLORO-5-CYANO-2-METHYL-NICOTINIC ACID ETHYL ESTER;Ethyl 6-chloro-5-cyano-2-methylpyridine-3-carboxylate;6-chloro-5-cyano-2-methyl-3-Pyridinecarboxylic acid ethyl ester;3-Pyridinecarboxylic acid, 6-chloro-5-cyano-2-methyl-, ethyl ester
• CAS NO: 64119-42-2
• Molecular Formula: C₁₀H₉ClN₂O₂
• Molecular Weight: 224.64366
• EINECS: -0
• Mol File: 64119-42-2.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: Ethyl 6-chloro-5-cyano-2-methylnicotinate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 6-chloro-5-cyano-2-methylnicotinate(64119-42-2)
• EPA Substance Registry System: Ethyl 6-chloro-5-cyano-2-methylnicotinate(64119-42-2)

Safety Data

• Hazardous Substances Data: 64119-42-2(Hazardous Substances Data)

Upstream product

• 52600-52-9 ethyl 5-cyano-6-hydroxy-2-methyl-pyridine-3-carboxylate 
• 137522-47-5 6-amino-5-cyano-2-methylnicotinic acid ethyl ester 
• 134653-70-6 ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate 
• 141-97-9 ethyl acetoacetate 
• 52600-52-9 5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester 

Downstream Products

• 103038-00-2 ethyl 5-cyano-2-methylnicotinate 
• 134828-39-0 5-Cyano-6-(2-methoxy-phenylamino)-2-methyl-nicotinic acid ethyl ester 
• 137522-53-3 2-cyclohexylamino-5-carbethoxy-6-methylnicotinonitrile 
• 134828-43-6 5-Cyano-2-methyl-6-p-tolylamino-nicotinic acid ethyl ester 
• 64119-43-3 6-anilino-5-cyano-2-methyl-nicotinic acid ethyl ester 
• 134828-41-4 2-(3'-methylphenylamino)-5-carbethoxy-6-methylnicotinonitrile 
• 139617-87-1 5-Cyano-6-(2,4-dimethyl-phenylamino)-2-methyl-nicotinic acid ethyl ester 
• 134828-40-3 5-Cyano-2-methyl-6-o-tolylamino-nicotinic acid ethyl ester 
• 137522-48-6 6-(benzylamino)-5-cyano-2-methylnicotinic acid ethyl ester 
• 134828-44-7 6-(3-Bromo-phenylamino)-5-cyano-2-methyl-nicotinic acid ethyl ester 
• 134828-42-5 6-(4-Bromo-phenylamino)-5-cyano-2-methyl-nicotinic acid ethyl ester 
• 137522-47-5 6-amino-5-cyano-2-methylnicotinic acid ethyl ester 
• 204765-68-4 3-amino-6-methyl-2phenylaminocarbonyl-5-ethoxycarbonylthieno[2,3-b]pyridine 
• 837412-26-7 2-(2-carboxyanilino)-5-ethoxycarbonyl-6-methylnicotinonitrile 

Relevant articles and documents

Discovery and optimization of thienopyridine derivatives as novel urea transporter inhibitors

Urea transporters (UTs) play an important role in the urine concentrating mechanism and are recognized as novel targets for developing small molecule inhibitors with salt-sparing diuretic activity. Thienoquinoline derivatives, a class of novel UT-B inhibitors identified by our group, play a significant diuresis in animal model. However, the poor solubility and low bioavailability limited its further development. To overcome these shortcomings, the structure modification of thienoquinoline was carried out in this study, which led to the discovery of novel thienopyridine derivatives as specific urea transporter inhibitors. Further optimization obtained the promising preclinical candidate 8n with not only excellent inhibition effect on urea transporters and diuretic activity on rat model, but also suitable water solubility and Log P value.

Development of a Multi-Kilogram-Scale Synthesis of AZD1283: A Selective and Reversible Antagonist of the P2Y12 Receptor

Ethyl 6-chloro-5-cyano-2-methylnicotinate (4) was coupled with 4-piperidinecarboxylic acid (isonipecotic acid) in 81% yield to pyridine acid 10. An amide coupling between 10 and benzylsulfonamide (6) afforded AZD1283 (1) in 79% yield using CDI as coupling reagent. The synthesis has been developed and scaled up to 20 kg batches of 1, supporting preclinical and clinical studies. Development work towards 2-chloropyridine 4 and benzylsulfonamide (6) is included.

Synthesis, inhibitory activity of cholinesterases, and neuroprotective profile of novel 1,8-naphthyridine derivatives

1,8-Naphthyridine derivatives related to 17 (ITH4012), a neuroprotective compound reported by our research group, have been synthesized. In general, they have shown better inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) than mo