GSK1349572 sodiuM salt

Base Information

• Chemical Name: GSK1349572 sodiuM salt
• CAS No.: 1051375-19-9
• Molecular Formula: C20H18F2N3O5. Na
• Molecular Weight: 441.367
• Mol file: 1051375-19-9.mol

Synonyms: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-7-hydroxy-4-methyl-6,8-dioxo-, sodium salt; Dolutegravir sodium

Chemical Property of GSK1349572 sodiuM salt

Chemical Property:

• PSA: 103.70000
• LogP: 2.11980
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated)

Purity/Quality:

99% ^*data from raw suppliers

Dolutegravir Sodium Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Dolutegravir sodium (Tivicay), developed and marketed by GlaxoSmithKline, was approved by the FDA in August 2013 as a novel integrase inhibitor for the treatment of HIV infection. Dolutegravir was fast-tracked by the FDA in February 2012, and joins an important class of drugs known as Integrase Strand Transfer inhibitors (INSTi’s). INSTi’s are characterized by their two-metal-chelating scaffolds, which are known to chelate Mg2+ cofactors in the enzyme active site, l interrupting function of HIV-1 integrase, which is essential for replication of viral DNA into host chromatin.Other drugs in this class, raltegravir and elvitegravir, are known to require either high dosages or PK boosting agents, respectively, with raltegravir also exhibiting substantial loss of potency in several major HIV-1 integrase mutation pathways. Dolutegravir was pursued with the goal of developing a novel INSTi with a once-daily, low-dosage treatment with improved resistance profile and without the need for the use of a PK boosting agent. Dolutegravir sodium has been approved for treating a broad population of HIV-infected patients, including adults undergoing their first treatment as well as those who have been treated with other integrase transfer strand inhibiting agents.

Technology Process of GSK1349572 sodiuM salt

There total 69 articles about GSK1349572 sodiuM salt which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

dolutegravir (1051375-16-6,1309560-49-3) → (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 (1051375-19-9)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 20 - 80 ℃; Product distribution / selectivity;

Reference yield: 98.9%

(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 (1206102-11-5) → (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 (1051375-19-9)

Guidance literature:

(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; With propylene glycol; palladium 10% on activated carbon; hydrogen; at 50 ℃;

With sodium t-butanolate; at 30 - 70 ℃; Temperature;

Reference yield: 90.0%

(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 (1335210-35-9) → (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 (1051375-19-9)

Guidance literature:

With methanol; sodium hydroxide; In butan-1-ol; at 100 ℃; Flow reactor; Large scale;

upstream raw materials:

dolutegravir

methyl 2-[(dimethylamino)methylene]-4-methoxy-3-oxobutanoate

methyl 2-(((2,2-dimethoxyethyl)amino)methylene)-4-methoxy-3-oxobutanoate

(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

Refernces

• 1、 -. "NOVEL CRYSTALLINE POLYMORPHS OF SODIUM (4R,12AS)-9-{[(2,4-DIFLUOROPHENYL) METHYL]CARBAMOYL}-4-METHYL-6,8-DIOXO-3,4,6,8,12,12A-HEXAHYDRO-2H-PYRIDO [1',2':4,5]PYRAZINO[2,1-B][1,3]OXAZIN-7-OLATE AND PROCESS FOR PREPARATION THEREOF". Page/Page column 19. . Retrieved 2020/08/22.
• 2、 -. "NEW POLYMORPHS OF DOLUTEGRAVIR SODIUM". Page/Page column 31; 32; 33; 34. . Retrieved 2019/04/10.