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

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

• 141-97-9 ethyl acetoacetate 
• 134653-70-6 ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate 
• 137522-47-5 6-amino-5-cyano-2-methylnicotinic acid ethyl ester 
• 52600-52-9 ethyl 5-cyano-6-hydroxy-2-methyl-pyridine-3-carboxylate 
• 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 
• 837412-26-7 2-(2-carboxyanilino)-5-ethoxycarbonyl-6-methylnicotinonitrile 
• 919351-41-0 ethyl 6-{4-[(benzylsulfonyl)carbamoyl]-piperidin-1-yl}-5-cyano-2-methylpyridine-3-carboxylate 

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, structure-property relationships and pharmacokinetic evaluation of ethyl 6-aminonicotinate sulfonylureas as antagonists of the P2Y12 receptor

The present paper describes the development of a new series of P2Y 12 receptor antagonists based on our previously reported piperazinyl urea series 1 (IC50 binding affinity = 0.33 μM, aq solubility 50 binding affinity = 0.042 μM, aq solubility = 90 μM, microsomal CLint (HLM) = 70 μM/min/mg). Further improvements in affinity and metabolic stability were achieved by replacing the central piperazine ring with a 3-aminoazetidine as exemplified by 3 (IC50 binding affinity = 0.0062 μM, aq solubility = 83 μM, microsomal CLint (HLM) = 28 μM/min/mg). The improved affinity observed in the in vitro binding assay also translated to the potency observed in the WPA aggregation assay (47: 19 nM and 3: 9.5 nM) and the observed in vitro ADME properties translates to the in vivo PK properties observed in rat. In addition, we found that the chemical stability of the sulfonylureas during prolonged storage in solution was related to the sulfonyl urea linker and depended on the type of solvent and the substitution pattern of the sulfonyl urea functionality.

Development of an efficient and practical route for the multikilogram manufacture of ethyl 5-cyano-2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate and ethyl 6-chloro-5-cyano-2-methylnicotinate, key intermediates in the preparation of P2Y12 antagonists

Elucidation of the mechanism of formation of two major impurities in the synthetic route towards key intermediate ethyl 5-cyano-2-methyl-6-oxo-1,6- dihydropyridine-3-carboxylate 1, led directly to the development of a route with significant process improvements in terms of yield, purity, and operability. The overall process yield increased from 15% to 73% without the need for extra purification steps, giving the key intermediate ethyl 6-chloro-5-cyano-2- methylnicotinate, 2, in excess of 80 kg to support clinical development.

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

2-AMINO-6-ALKYL SUBSTITUTED PYRIDINE DERIVATIVES USEFUL AS P2Y12 INHIBITORS 308

The present invention relates to certain new pyridin analogues of Formula ( I ) to processes for preparing such compounds, to their utility as P2Y12 inhibitors and as anti-trombotic agents etc, their use as medicaments in cardiovascular disease

The sandmeyer reaction on some selected heterocyclic ring systems: Synthesis of useful 2-chloroheterocyclic-3-carbonitrile intermediates

The Sandmeyer reaction on some selected heterocycles bearing the 2-amino-3-carbonitrile structural moiety has been investigated in order to prepare the corresponding 2-chloro-3-carbonitrile derivatives as synthetic useful intermediates for further develop

New Pyridine Analogues IV

The present invention relates to certain new pyridin analogues of Formula (I) to processes for preparing such compounds, to their utility as P2Y12 inhibitors and as anti-trombotic agents etc, their use as medicaments in cardiovascular diseases

NEW PYRIDINE ANALOGUES

The present invention relates to certain new pyridin analogues of Formula ( I ) to processes for preparing such compounds, to their utility as P2Y12 inhibitors and as anti-trombotic agents etc, their use as medicaments in cardiovascular disease

NEW PYRIDINE ANALOGUES

The present invention relates to certain new pyridin analogues of Formula ( I ) to processes for preparing such compounds, to their utility as P2Y12 inhibitors and as anti-trombotic agents etc, their use as medicaments in cardiovascular disease