Production Method 1

22282-72-0

89937-77-9

Reaction Conditions

1.1 Reagents: Thionyl chloride ;  0 °C; 12 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  pH 8, rt

Reference

Synthesis and biological evaluation of a series of novel pyridinecarboxamides as potential multi-receptor antipsychotic drugs

Xu, Mingshuo ; Wang, Yu; Yang, Feipu; Wu, Chunhui; Wang, Zhen ; et al, Bioorganic & Medicinal Chemistry Letters, 2018, 28(4), 606-611

Production Method 2

3783-38-8

89937-77-9

Reaction Conditions

1.1 Reagents: Acetic anhydride ;  5 min, 25 °C → 185 °C; 2 h, 185 °C; 185 °C → 30 °C
1.2 Reagents: Alumina Solvents: Methanol ;  3 min, 30 °C → 100 °C; 1 h, 100 °C

Reference

Matrix-assisted laser desorption/ionization tandem mass spectrometry of N-glycans derivatized with isonicotinic hydrazide and its biotinylated form

Bank, Stephanie; Heller, Eberhard; Memmel, Elisabeth; Seibel, Juergen; Holzgrabe, Ulrike; et al, Rapid Communications in Mass Spectrometry, 2014, 28(15), 1745-1756

Production Method 3

22282-72-0

89937-77-9

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  12 h, 0 °C

Reference

Discovery, design, and synthesis of indole-based EZH2 inhibitors

Gehling, Victor S.; Vaswani, Rishi G.; Nasveschuk, Christopher G.; Duplessis, Martin; Iyer, Priyadarshini; et al, Bioorganic & Medicinal Chemistry Letters, 2015, 25(17), 3644-3649

Production Method 4

6937-03-7

89937-77-9

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Sulfuric acid Solvents: Water ;  rt; rt → 0 °C; 0 °C; 3 h, 22 °C; 1 min, reflux
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized
1.3 Reagents: Methanol ,  Sulfuric acid Solvents: Methanol ,  Water ;  15 h, reflux; reflux → 22 °C
1.4 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized

Reference

Inhibition of chorismate-utilising enzymes by 2-amino-4-carboxypyridine and 4-carboxypyridone and 5-carboxypyridone analogues

Payne, Richard J.; Bulloch, Esther M. M.; Kerbarh, Olivier; Abell, Chris, Organic & Biomolecular Chemistry, 2010, 8(15), 3534-3542

Production Method 5

6313-54-8

89937-77-9

6937-03-7

Reaction Conditions

1.1 Reagents: Ammonia Solvents: Water ;  22 h, 240 °C
1.2 Reagents: Sulfuric acid Solvents: Water ;  rt; 18 h, 75 °C

Reference

Discovery of an N-(2-aminopyridin-4-ylmethyl)nicotinamide derivative: a potent and orally bioavailable NCX inhibitor

Kuramochi, Takahiro; Kakefuda, Akio; Yamada, Hiroyoshi; Tsukamoto, Issei; Taguchi, Taku; et al, Bioorganic & Medicinal Chemistry, 2005, 13(12), 4022-4036

Production Method 6

3783-38-8

89937-77-9

Reaction Conditions

1.1 Reagents: Acetic anhydride

Reference

Synthesis of 4-[2-[N-[1-methyl-3-(3-carbamylphenyl)propyl]amino]ethyl]-1-hydroxy-2-pyridone

Yoon, Sung Hwa, Yakhak Hoechi, 1993, 37(1), 36-40

methyl 2-oxo-1H-pyridine-4-carboxylate Raw materials

• Methyl Isonicotinate N-Oxide
• Methyl 2-aminoisonicotinate
• 2-chloropyridine-4-carboxylic acid
• 2-hydroxypyridine-4-carboxylic acid

methyl 2-oxo-1H-pyridine-4-carboxylate Preparation Products

• Methyl 2-aminoisonicotinate (6937-03-7)
• methyl 2-oxo-1H-pyridine-4-carboxylate (89937-77-9)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridinecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridinecarboxylic acids and derivatives Pyridinecarboxylic acids

Methyl 2-oxo-1H-pyridine-4-carboxylate (CAS No. 89937-77-9): A Key Intermediate in Modern Pharmaceutical Synthesis

Methyl 2-oxo-1H-pyridine-4-carboxylate, identified by its unique chemical identifier CAS No. 89937-77-9, is a significant compound in the realm of pharmaceutical chemistry. This heterocyclic ester serves as a crucial intermediate in the synthesis of various biologically active molecules, particularly those targeting neurological and cardiovascular disorders. The compound's structural framework, featuring a pyridine ring with a methyl ester group and a β-keto ester moiety, makes it a versatile building block for medicinal chemists.

The utility of methyl 2-oxo-1H-pyridine-4-carboxylate stems from its ability to undergo a wide array of chemical transformations. These include condensation reactions with amines to form pyridine derivatives, cyclization processes to create more complex heterocycles, and Michael additions to α,β-unsaturated carbonyl compounds. Such reactivity has positioned it as an indispensable component in the development of novel therapeutic agents.

In recent years, the pharmaceutical industry has witnessed an increasing demand for innovative treatments for chronic diseases. Among these, neurological disorders such as Alzheimer's disease and Parkinson's disease have garnered significant attention. Researchers have leveraged the structural features of methyl 2-oxo-1H-pyridine-4-carboxylate to design molecules that modulate neurotransmitter activity. For instance, derivatives of this compound have been explored as potential acetylcholinesterase inhibitors, which are pivotal in managing cognitive decline associated with neurodegenerative conditions.

The synthesis of methyl 2-oxo-1H-pyridine-4-carboxylate itself is an area of active research. Modern synthetic methodologies emphasize efficiency, scalability, and sustainability. One such approach involves the catalytic conversion of readily available pyridine precursors using transition metal catalysts. These methods not only enhance yield but also minimize waste, aligning with green chemistry principles. Recent advances in flow chemistry have further refined the production process, enabling continuous manufacturing that reduces batch-to-batch variability.

Beyond its role in drug discovery, methyl 2-oxo-1H-pyridine-4-carboxylate has found applications in agrochemicals and material science. Its derivatives exhibit properties that make them suitable for use as intermediates in the synthesis of pesticides and specialty chemicals. Additionally, the compound's ability to form stable complexes with metals has been exploited in the development of novel catalysts and coordination polymers.

The pharmacological profile of compounds derived from methyl 2-oxo-1H-pyridine-4-carboxylate continues to be a subject of intense investigation. Preclinical studies have highlighted its potential in treating not only neurological disorders but also cardiovascular diseases. The ester functionality allows for facile modifications that can fine-tune solubility, bioavailability, and metabolic stability, making it an attractive scaffold for structure-based drug design.

As computational chemistry advances, virtual screening techniques are being employed to identify novel analogs of methyl 2-oxo-1H-pyridine-4-carboxylate. Machine learning models predict biological activity based on molecular descriptors, expediting the discovery process. This interdisciplinary approach combines experimental expertise with computational power to accelerate the development pipeline.

The regulatory landscape for pharmaceutical intermediates like methyl 2-oxo-1H-pyridine-4-carboxylate is stringent but evolving. Regulatory agencies worldwide are increasingly focusing on sustainability and ethical sourcing of raw materials. Manufacturers must adhere to Good Manufacturing Practices (GMP) and ensure that their processes meet environmental standards. This has driven innovation in synthetic routes that prioritize safety and ecological responsibility.

In conclusion, methyl 2-oxo-1H-pyridine-4-carboxylate (CAS No. 89937-77-9) is a multifaceted compound with far-reaching implications in pharmaceutical research and industrial applications. Its structural versatility and reactivity make it a cornerstone in the synthesis of life-saving drugs and advanced materials. As scientific understanding progresses and technology evolves, the role of this compound is poised to expand even further into uncharted territories of medicine and material science.

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• 18617-50-0(Ethyl 6-hydroxynicotinate)
• 61327-53-5(4-Pyridinecarboxylic acid, 1,2-dihydro-1,3-dimethyl-2-oxo-, methyl ester)
• 247101-81-1(4-Pyridinecarboxylicacid, 6-amino-1,2-dihydro-2-oxo-, methyl ester)
• 66171-50-4(methyl 6-oxo-1,6-dihydropyridine-3-carboxylate)
• 22282-72-0(2-hydroxypyridine-4-carboxylic acid)
• 98996-29-3(Ethyl 1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate)