1206102-08-0

Basic information

• Product Name: Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate
• Synonyms: Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate;methyl 3-(benzyloxy)-1,4-dihydro-1-(2,2-dihydroxyethyl)-4-oxopyridine-2-carboxylate;Methyl 1-(2,2-dihydroxyethyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate;2-Pyridinecarboxylic acid, 1-(2,2-dihydroxyethyl)-1,4-dihydro-4-oxo-3-(phenylmethoxy)-, methyl ester
• CAS NO: 1206102-08-0
• Molecular Formula: C₁₆H₁₇NO₆
• Molecular Weight: 319.30928
• EINECS: -0
• Mol File: 1206102-08-0.mol

Chemical Properties

• Boiling Point: 542.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.38±0.1 g/cm3(Predicted)
• PKA: 12.54±0.41(Predicted)
• CAS DataBase Reference: Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate(1206102-08-0)
• EPA Substance Registry System: Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate(1206102-08-0)

Safety Data

• Hazardous Substances Data: 1206102-08-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate is used as a cardiovascular agent for its potential to modulate calcium channels, which is crucial in the treatment of various heart conditions. Its interaction with these channels can lead to the regulation of heart rate and blood pressure, making it a promising candidate for the development of new cardiovascular drugs.
Additionally, due to its chemical structure, it can be used as a precursor in the synthesis of other dihydropyridine-based pharmaceuticals, contributing to the discovery and development of novel therapeutic agents with improved efficacy and safety profiles.
Used in Chemical Research:
In the field of chemical research, Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate serves as a valuable compound for studying the structure-activity relationships of dihydropyridines. Its unique ester and benzyloxy substituents provide opportunities for exploring the effects of these functional groups on the compound's biological activity and pharmacokinetic properties. This research can lead to a better understanding of the underlying mechanisms of action and the optimization of dihydropyridine-based drugs for various therapeutic applications.

Upstream product

• 1206102-07-9 1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid methyl ester 
• 119736-16-2 3-(benzyloxy)-1-((tert-butoxycarbonyl)amino)-4-oxo-1,4-dihydropyridine-2-carboxylic acid ethyl ester 
• 1206102-06-8 1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid 
• 118-71-8 Maltol 
• 100-39-0 benzyl bromide 
• 61049-69-2 3-O-benzylmaltol 
• 1206102-04-6 2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one 
• 1206102-05-7 2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one 
• 1229006-11-4 C₂₀H₁₆O₃ 
• 500371-01-7 3-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde 

Downstream Products

• 1206103-43-6 (3S,11aR)-3-methyl-6-[(phenylmethyl)oxy]-2,3,11,11a-tetrahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-5,7-dione 
• 1206102-09-1 (4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione 

Relevant articles and documents

Practical and Scalable Synthetic Method for Preparation of Dolutegravir Sodium: Improvement of a Synthetic Route for Large-Scale Synthesis

A practical and scalable synthetic method to obtain dolutegravir sodium (1) was established starting from the readily accessible material maltol (2). This synthetic method includes a scalable oxidation process of maltol and palladium-catalyzed amidation for introduction of an amide moiety, leading to a practical manufacturing method in short synthetic steps. The synthetic method demonstrated herein enables multikilogram scale manufacturing of 1 of high purity.

Practical Synthetic Method for the Preparation of Pyrone Diesters: An Efficient Synthetic Route for the Synthesis of Dolutegravir Sodium

A highly efficient and practical synthetic method for the preparation of pyrone diesters was established. The pyrone diester 3c can be prepared from readily available starting materials on a multihundred gram scale. The pyrone diester 3c can easily be converted to dolutegravir sodium (1). The synthetic route demonstrated herein provides an efficient and atom-economical synthetic method for preparing this potent anti-HIV agent.

Improved method for synthesizing dolutegravir

The invention relates to an improved method for synthesizing dolutegravir and belongs to the field of medicinal chemistry. The method takes maltol (compound 1) as a raw material, and a target is synthesized by the following route. The process raw material is cheap and easy to obtain, a reaction solvent can be recycled, the post-treatment operation is simple, the yield and the purity are high, especially the carbamoylation and debenzylation reaction are carried out in one step, the synthesis route is simplified, the cost is reduced, and the large-scale industrial production is facilitated.

Intermediate of these pyridonecarboxylic carbamoylalkanoic and HIV integrase inhibitor

A synthesis approach providing an early ring attachment via a bromination to compound I-I yielding compound II-II: whereby a final product such as AA: can be synthesized. In particular, the 2,4-difluorophenyl-containing sidechain is attached before creation of the additional ring Q.

TETRACYCLIC HETEROCYCLE COMPOUNDS USEFUL AS HIV INTEGRASE INHIBITORS

The present invention relates to Tetracyclic Heterocycle Compounds of Formula (I) and pharmaceutically acceptable salts or prodrug thereof, wherein n, X, Y, Z, R1, R2, and R3 are as defined herein. The present invention also relates to compositions comprising at least one Tetracyclic Heterocycle Compound, and methods of using the Tetracyclic Heterocycle Compounds for treating or preventing HIV infection in a subject.

(3S,11aR)-6-[(phenylmethyl)oxy]-3-methyl-2,3,11,11a-tetrahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-5,7-dione of the formula P-9 and/or (3S,11aR)-6-[(phenymethyl)oxy]-8-bromo-3-methyl-2,3,11,11a-tetrahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-5,7-dione of the formula P-10

The compounds are intermediates in the preparation of therapeutic agents useful in the treatment of viral infections, particularly HIV infection. The compounds are (3S,11aR)-6-[(phenylmethyl)oxy]-3-methyl-2,3,11,11a-tetrahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-5,7-dione of the formula P-9 and/or (3S,11aR)-6-[(phenylmethyl)oxy]-8-bromo-3-methyl-2,3,11,11a-tetrahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-5,7-dione of the formula P-10.

PROCESSES AND INTERMEDIATES FOR CARBAMOYLPYRIDONE HIV INTEGRASE INHIBITORS

Processes are provided which create an aldehyde methylene, or hydrated or hemiacetal methylene attached to a heteroatom of a 6 membered ring without going through an olefinic group and without the necessity of using an osmium reagent. In particular, a comopound of formula (I) can be produced from (II) and avoid the use of an allyl amine: (formulae I and II) where R, P 1 P3, R3 and Rx are as described herein.