1335210-23-5

Basic information

• Product Name: 1-(2,2-diMethoxyethyl)-5-Methoxy-6-(Methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid
• Synonyms: Dulotegravir Me-N-4;1-(2,2-Dimethoxyethyl)-1,4-dihydro-3-methoxy-4-oxo-2,5-pyridinedicarboxylic acid 2-methyl ester;1-[2,2-bis(methyloxy)ethyl]-5-(methyloxy)-6-[(methyloxy)carbonyl]-4-oxo-1,4-dihydro-3-pyridinecarboxylic acid;1-(2,2-diMethoxyethyl)-5-Methoxy-6-(Methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid;2,5-Pyridinedicarboxylic acid, 1-(2,2-dimethoxyethyl)-1,4-dihydro-3-methoxy-4-oxo-, 2-methyl ester;Dolutegravir Intermediates3;1-(2,2-Dimethoxyethyl)-1,4-dihydro-3-methoxy-4-oxo-2,5-pyridinedicarboxylic acid 2-methyl este;1-(2,2-dimethoxyethyl)-5-methoxy-4-oxo-1,4-dihydropyridine-3,6-dicarboxylic acid-6-methyl ester
• CAS NO: 1335210-23-5
• Molecular Formula: C₁₃H₁₇NO₈
• Molecular Weight: 315.27598
• EINECS: -0
• Product Categories: CMLLYL
• Mol File: 1335210-23-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 474.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.36±0.1 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 5.56±0.40(Predicted)
• CAS DataBase Reference: 1-(2,2-diMethoxyethyl)-5-Methoxy-6-(Methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,2-diMethoxyethyl)-5-Methoxy-6-(Methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid(1335210-23-5)
• EPA Substance Registry System: 1-(2,2-diMethoxyethyl)-5-Methoxy-6-(Methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid(1335210-23-5)

Safety Data

• Hazardous Substances Data: 1335210-23-5(Hazardous Substances Data)

Usage

Description

1-(2,2-diMethoxyethyl)-5-Methoxy-6-(Methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid is a complex organic compound with a unique structure that features a pyridine ring and multiple methoxy and carbonyl groups. This molecule is characterized by its potential reactivity and functional groups, which can be utilized in various chemical reactions and applications.

Uses

Used in Pharmaceutical Industry:
1-(2,2-diMethoxyethyl)-5-Methoxy-6-(Methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid is used as a key intermediate in the synthesis of Dolutegravir, a potent HIV integrase inhibitor. Its unique structure and functional groups play a crucial role in the development of this medication, which is designed to combat the replication of the HIV virus in infected cells.
As an intermediate in the synthesis of GSK1265744 (I), this compound contributes to the development of new therapeutic agents that can help manage and treat HIV infections more effectively. The presence of multiple reactive sites on the molecule allows for further chemical modifications and the creation of related compounds with potential applications in medicine and other fields.

Upstream product

• 553-90-2 Dimethyl oxalate 
• 22483-09-6 2,2-dimethoxyethylamine 
• 1335210-26-8 methyl 2-(((2,2-dimethoxyethyl)amino)methylene)-4-methoxy-3-oxobutanoate 
• 127958-23-0 methyl 2-[(dimethylamino)methylene]-4-methoxy-3-oxobutanoate 
• 41051-15-4 4-methoxyacetoacetic acid methylester 

Downstream Products

• 1335210-24-6 (3S,11aR)-3-methyl-6-(methyloxy)-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxylic acid 
• 1051375-10-0 (3S,11aR)-N-[(2,4-difluorophenyl)methyl]-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide 
• 1335210-25-7 (4R,12aS)-N-(2,4-difluorobenzyl)-7-methoxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1’,2’:4,5]pyrazino[2,1-b]oxazine-9-carboxamide 
• 1051375-10-0 (3S,11aS)-N-(2,4-difluorobenzyl)-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide 
• 1616340-68-1 methyl 5-((2,4-difluorobenzyl)carbamoyl)-1-(2,2-dirnethoxyethyl)-3-methoxy-4-oxo-1,4-dihydropyridine-2-carboxylate 
• 1335210-35-9 (4R,12aS)-N-(2,4-difluorobenzyl)-7-methyloxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido [1',2',:4,5]pyrazino[2,1-b] [1,3]oxazine-9-carboxamide 
• 1051375-16-6 dolutegravir 
• 1335210-34-8 (4R,12aS)-7-methoxy-4-methyl-6,8-dioxo-3,4,6,8, 12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxylic acid 

Relevant articles and documents

Preparation of the key dolutegravir intermediate via MgBr2-promoted cyclization

A novel approach for synthesizing the key dolutegravir intermediate is described via MgBr2-promoted intramolecular cyclization. Condensation of commercially available methyl oxalyl chloride and ethyl 3-(N,N-dimethylamino)acrylate afforded the vinylogous amide in an excellent yield. Subsequent substitution by aminoacetaldehyde dimethyl acetal and methyl bromoacetate gave rise to the expected precursor for cyclization, which was promoted by MgBr2 to highly selectively convert into pyridinone diester. The key dolutegravir intermediate was finally prepared by the selective hydrolysis of the corresponding diester via LiOH.

CONTINUES FLOW PROCESS FOR THE PREPARATION OF ACTIVE PHARMACEUTICAL INGREDIENTS - POLYCYCLIC CARBAMOYL PYRIDONE DERIVATIVES AND INTERMEDIATES THEREOF

The present invention discloses continues flow process for the preparation of polycyclic carbamoyl pyridone derivatives and intermediates thereof. In particular, the present invention discloses a process for the preparation of intermediate. Formule (V).

Preparation of Dolutegravir Intermediate Diastereomer

A convenient method was developed to prepare the diastereomer of dolutegravir tricyclic intermediate in the catalysis of EDCI/DMAP in up to 87% yield. Different solvents, temperature, and times were optimized. The synthesized diastereomer 6′ could be used as a standard for the industrial manufacture requirement of dolutegravir active pharmaceutical ingredient.