1206102-11-5

Basic information

• Product Name: (4R,12aS)-N-(2,4-difluorobenzyl)-7-benzylhydroxy-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
• Synonyms: (4R,12aS)-N-(2,4-difluorobenzyl)-7-benzylhydroxy-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;(4R,12aS)-7-(benzyloxy)-N-(2,4-difluorobenzyl)-4-Methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-[1,3]oxazino[3,2-d]pyrido[1,2-a]pyrazine-9-carboxaMide;(4R,12aS)-N-[(2,4-Difluorophenyl)methyl]-3,4,6,8,12,12a-hexahydro-4-methyl-6,8-dioxo-7-(phenylmethoxy)-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide;Dolutegravir Intermediate4;(4R,12aS)-7-(benzyloxy)-N-(2,4-difluorobenzyl)-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;3 4 6-TRICHLOROBENZYL ALCOHOL 97;2H-Pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide, N-[(2,4-difluorophenyl)methyl]-3,4,6,8,12,12a-hexahydro-4-methyl-6,8-dioxo-7-(phenylmethoxy)-, (4R,12aS)-;(4R,12aS)-N-(2,4-difluorobenzyl)-7-benzylhydroxy-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-carboxa
• CAS NO: 1206102-11-5
• Molecular Formula: C₂₇H₂₅F₂N₃O₅
• Molecular Weight: 509.5013064
• Product Categories: Dolutegravir INTERMEDIATES
• Mol File: 1206102-11-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 761.7±60.0 °C(Predicted)
• Appearance: /
• Density: 1.42±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.67±0.40(Predicted)
• CAS DataBase Reference: (4R,12aS)-N-(2,4-difluorobenzyl)-7-benzylhydroxy-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(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,12aS)-N-(2,4-difluorobenzyl)-7-benzylhydroxy-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(1206102-11-5)
• EPA Substance Registry System: (4R,12aS)-N-(2,4-difluorobenzyl)-7-benzylhydroxy-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(1206102-11-5)

Safety Data

• Hazardous Substances Data: 1206102-11-5(Hazardous Substances Data)

Usage

Uses

(4R,12aS)-N-[(2,4-Difluorophenyl)methyl]-3,4,6,8,12,12a-hexahydro-4-methyl-6,8-dioxo-7-(phenylmethoxy)-2H-pyrido[1'',2'':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide is a Dolutegravir (D528800) intermediate and an antiviral agent. Dolutegravir is a second generation HIV-1 integrase strand transfer inhibitor.

Upstream product

• 1206102-05-7 2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one 
• 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 
• 72235-52-0 2,4-Difluoro-benzylamine 
• 1229006-25-0 methyl 3-(benzyloxy)-5-(2,4-difluorobenzylcarbamoyl)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2-carboxylate 
• 1206102-08-0 methyl 1-(2,2-dihydroxyethyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate 
• 1206102-07-9 1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid methyl ester 
• 1206102-06-8 1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid 
• 119736-16-2 3-(benzyloxy)-1-((tert-butoxycarbonyl)amino)-4-oxo-1,4-dihydropyridine-2-carboxylic acid ethyl ester 
• 1229006-11-4 C₂₀H₁₆O₃ 
• 1206102-04-6 2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one 
• 500371-01-7 3-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde 
• 61049-69-2 3-O-benzylmaltol 
• 100-39-0 benzyl bromide 

Downstream Products

• 1051375-16-6 dolutegravir 
• 1051375-19-9 (4R,12aS)-N-(2,4-difluorobenzyl)-7-hydroxy-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 sodium salt 
• 1339879-88-7 C₃₂H₃₃F₂N₃O₇ 
• 1339879-96-7 C₂₅H₂₅N₃O₅S 
• 1339877-65-4 C₂₀H₂₇N₃O₅ 
• 1339879-93-4 C₂₇H₃₃N₃O₅ 
• 1339879-91-2 (4R,12aS)-3,4,6,8,12,12a-hexahydro-4-methyl-6,8-dioxo-7-(phenylmethoxy)-2H-pyrido [1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxylic acid 

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.

Identification and Control of Critical Process Impurities: An Improved Process for the Preparation of Dolutegravir Sodium

A four-stage manufacturing route for the preparation of dolutegravir sodium (1) was assessed and optimized leading to a higher yielding, simpler and scalable process. Key improvements in the process include the development of mild workup procedure by selective derivatization of a difficult to remove a process impurity using tert-butyldimethylsilyl chloride. Metal-based hydrogenation-free O-debenzylation is optimized, and the critical isomeric impurity formed was identified and eliminated from the process by the establishment of a proper control strategy.

DOLUTEGRAVIR SALTS

Dolutegravir potassium salt and solid state forms thereof are provided, as well as methods of making and interconverting these forms. The Dolutegravir potassium forms, and pharmaceutical compositions containing them, may be used to treat subjects in need