(3S,11aR)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-d]pyrido[1,2-a]pyrazine-8-carboxylic acid

Base Information

• Chemical Name: (3S,11aR)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-d]pyrido[1,2-a]pyrazine-8-carboxylic acid
• CAS No.: 1335210-25-7
• Molecular Formula: C₂₀H₁₉F₂N₃O₅
• Molecular Weight: 419.385
• Mol file: 1335210-25-7.mol

Synonyms:(3S,11aR)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-d]pyrido[1,2-a]pyrazine-8-carboxylic acid;(3S,11aR)-N-(2,4-difluorobenzyl)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-d]pyrido[1,2-a]pyrazine-8-carboxamide

Chemical Property of (3S,11aR)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-d]pyrido[1,2-a]pyrazine-8-carboxylic acid

Chemical Property:

• Boiling Point: 679.1±55.0 °C(Predicted)
• PKA: 10.65±0.40(Predicted)
• Density: 1.48±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

(3S,11AR)-N-(2,4-difluorobenzyl)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,11aR)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-d]pyrido[1,2-a]pyrazine-8-carboxylic acid

There total 15 articles about (3S,11aR)-6-methoxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-d]pyrido[1,2-a]pyrazine-8-carboxylic acid 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: 67.0%

(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 (1335210-24-6) + 2,4-Difluoro-benzylamine (72235-52-0) → (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 (1335210-25-7)

Guidance literature:

With pivaloyl chloride; triethylamine; In dichloromethane; at 0 - 30 ℃;

Reference yield:

1-[2,2-bis(methyloxy)ethyl]-5-(methyloxy)-6-[(methyloxy)carbonyl]-4-oxo-1,4-dihydro-3-pyridinecarboxylic acid (1335210-23-5) → (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 (1335210-25-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid / methanesulfonic acid / acetonitrile / 19.5 h / 58 - 65 °C

1.2: 16.5 h / 64 °C

2.1: 1,1'-carbonyldiimidazole / 1,2-dimethoxyethane / 1 h / 80 °C

2.2: 1 h / 20 °C

With acetic acid; 1,1'-carbonyldiimidazole; methanesulfonic acid; In 1,2-dimethoxyethane; acetonitrile;

Reference yield:

methyl 2-(((2,2-dimethoxyethyl)amino)methylene)-4-methoxy-3-oxobutanoate (1335210-26-8) → (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 (1335210-25-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hydride / methanol / 14 h / -25 - 40 °C

1.2: 1 h / -5 - 5 °C

1.3: -5 °C

2.1: acetic acid / methanesulfonic acid / acetonitrile / 19.5 h / 58 - 65 °C

2.2: 16.5 h / 64 °C

3.1: 1,1'-carbonyldiimidazole / 1,2-dimethoxyethane / 1 h / 80 °C

3.2: 1 h / 20 °C

With lithium hydride; acetic acid; 1,1'-carbonyldiimidazole; methanesulfonic acid; In methanol; 1,2-dimethoxyethane; acetonitrile;

upstream raw materials:

4-methoxyacetoacetic acid methylester

(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

2,4-Difluoro-benzylamine

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

Downstream raw materials:

(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

Refernces

• 1、 -. "CONTINUES FLOW PROCESS FOR THE PREPARATION OF ACTIVE PHARMACEUTICAL INGREDIENTS - POLYCYCLIC CARBAMOYL PYRIDONE DERIVATIVES AND INTERMEDIATES THEREOF". . . Retrieved 2019/09/04.
• 2、 -. "PROCESS FOR PREPARING CARBAMOYLPYRIDONE DERIVATIVES AND INTERMEDIATES". . . Retrieved 2011/10/13.