1-(2,2-diMethoxyethyl)-5-Methoxy-6-(Methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid Chemical Properties

Boiling point:

474.1±45.0 °C(Predicted)

Density 

1.36±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform, DMSO (Slightly), Methanol (Slightly)

pka

5.56±0.40(Predicted)

form 

Solid

color 

White to Light Yellow

1-(2,2-diMethoxyethyl)-5-Methoxy-6-(Methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid Usage And Synthesis

Uses

Dolutegravir intermediate-1 (1-(2,2-diMethoxyethyl)-5-Methoxy-6-(Methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid) is used as an intermediate in the synthesis of GSK1265744 (I), a potent HIV integrase inhibitor.

Synthesis

N, N-Dimethylformamide dimethyl acetal was added to methyl 4-methoxy-3-oxobutanoate, and the mixture was kept for 2 h at 25-30°C. The resulting methyl2-(dimethylaminomethylidene)-4-methoxy-3-oxobutanoate was dissolved in methanol, 2-amino acetaldehyde dimethyl acetal was added, and the mixture was stirred at20-30°C for 2 h. The solvent was removed under reduced pressure, the residue was diluted with methanol, and dimethyl oxalate was added at 25-30°C. The mixture was cooled to 0-5°C, 30 wt % sodium methoxide in methanol was slowly added, and the mixture was slowly heated to 40°C, stirred for 14 h at that temperature, and concentrated under reduced pressure. The residue was diluted with dichloromethane and poured into cold (0-5°C)2 N aqueous HCl. The organic phase was separated, the aqueous layer was extracted with dichloromethane (2× ), and the combined organic layers were washed with demineralized water and concentrated under reduced pressure at 40-45 °C to obtain intermediate. The product was dissolved in methanol, the solution was cooled to 0-5°C, and lithium hydroxide monohydrate was added. The mixture was stirred at 0-5°C for 3 h, quenched with 2 N aqueous HCl, and extracted with ethyl acetate (3×). Finally, the product 1-(2,2-diMethoxyethyl)-5-Methoxy-6-(Methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid can be obtained through further purification.

1-(2,2-diMethoxyethyl)-5-Methoxy-6-(Methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid(1335210-23-5)Related Product Information

• (1R,3S)-3-Aminocyclopentanol
• (1S,3R)-3-Aminocyclopentanol
• Salmeterol
• 1-(4-Acetyloxy)-3-((acetyloxy)methyl)phenyl)-2-bromoethanone
• 5-(2R)-2-Oxiranyl-8-benzyloxy-2(1H)-quinolinone
• Bictegravir
• GSK1349572
• 2-BROMO-1-[4-HYDROXY-3-(HYDROXYMETHYL)PHENYL]ETHAN-1-ONE
• O-Methyl Dolutegravir
• 4-Acetoxy-3-acetoxymethylacetophenone
• (6a,11b,16a,17a)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic acid
• (4R,12aS)-7-Methoxy-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-carboxylic acid
• N-(2-Chloropyrimidin-4-YL)-2,3-dimethyl-2H-indazol-6-amine
• N-(2-chloropyriMidin-4-yl)-N,2,3-triMethyl-2H-indazol-6-aMine
• (2R,5S,13aR)-8-methoxy-7,9-dioxo-N-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide
• 2,4,6-TRIFLUOROBENZYL AMINE
• (2R,5S,13aR)-8-methoxy-7,9-dioxo-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxylic acid
• BIS(3,5-DIBROMOSALICYL) FUMARATE