8-(1-(3,5-difluorophenylamino)ethyl)-N-(2-methoxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

Base Information

• Chemical Name: 8-(1-(3,5-difluorophenylamino)ethyl)-N-(2-methoxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide
• CAS No.: 1296271-07-2
• Molecular Formula: C₂₆H₂₉F₂N₃O₅
• Molecular Weight: 501.53

Synonyms:8-(1-(3,5-difluorophenylamino)ethyl)-N-(2-methoxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

Chemical Property of 8-(1-(3,5-difluorophenylamino)ethyl)-N-(2-methoxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-(1-(3,5-difluorophenylamino)ethyl)-N-(2-methoxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

There total 11 articles about 8-(1-(3,5-difluorophenylamino)ethyl)-N-(2-methoxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide 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: 62.0%

N-methyl-N-(2-methoxyethyl)amine (38256-93-8) + 8-(1-(3,5-difluorophenylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (1296271-55-0,1296271-56-1,1296271-57-2) → 8-(1-(3,5-difluorophenylamino)ethyl)-N-(2-methoxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (1296271-07-2)

Guidance literature:

8-(1-(3,5-difluorophenylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid; With O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 2h; Inert atmosphere;

N-methyl-N-(2-methoxyethyl)amine; In dichloromethane; at 35 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm501629p

Reference yield:

methyl 3-acetyl-5-bromo-4-hydroxybenzoate (160753-84-4) → 8-(1-(3,5-difluorophenylamino)ethyl)-N-(2-methoxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (1296271-07-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: boron trifluoride diethyl etherate / toluene / 18 h / 25 °C / Inert atmosphere

1.2: 12 h / 90 °C / Inert atmosphere

2.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 21 h / 90 °C / Inert atmosphere

2.2: 0.5 h / 45 °C / Inert atmosphere

3.1: sodium tetrahydroborate / dichloromethane; methanol / 0.25 h / -10 °C / Inert atmosphere

4.1: phosphorus tribromide / dichloromethane / 36 h / 0 - 25 °C / Inert atmosphere

5.1: potassium iodide / methanol; chloroform / 48 h / 25 °C / Inert atmosphere

6.1: sodium hydroxide; water / tetrahydrofuran; methanol / 18 h / 25 °C / Inert atmosphere

7.1: O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 25 °C / Inert atmosphere

7.2: 2 h / 35 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; boron trifluoride diethyl etherate; water; phosphorus tribromide; O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; potassium iodide; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; toluene; 2.1: |Stille Cross Coupling / 2.2: |Stille Cross Coupling;

DOI:10.1021/jm501629p

Reference yield:

methyl 3-acetyl-4-hydroxybenzoate (57009-12-8) → 8-(1-(3,5-difluorophenylamino)ethyl)-N-(2-methoxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (1296271-07-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: bromine; pyridine / dichloromethane / 2 h / 0 - 25 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / toluene / 18 h / 25 °C / Inert atmosphere

2.2: 12 h / 90 °C / Inert atmosphere

3.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 21 h / 90 °C / Inert atmosphere

3.2: 0.5 h / 45 °C / Inert atmosphere

4.1: sodium tetrahydroborate / dichloromethane; methanol / 0.25 h / -10 °C / Inert atmosphere

5.1: phosphorus tribromide / dichloromethane / 36 h / 0 - 25 °C / Inert atmosphere

6.1: potassium iodide / methanol; chloroform / 48 h / 25 °C / Inert atmosphere

7.1: sodium hydroxide; water / tetrahydrofuran; methanol / 18 h / 25 °C / Inert atmosphere

8.1: O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 25 °C / Inert atmosphere

8.2: 2 h / 35 °C / Inert atmosphere

With pyridine; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; boron trifluoride diethyl etherate; water; bromine; phosphorus tribromide; O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; potassium iodide; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; toluene; 3.1: |Stille Cross Coupling / 3.2: |Stille Cross Coupling;

DOI:10.1021/jm501629p

upstream raw materials:

methyl 8-(1-bromoethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate

N-methyl-N-(2-methoxyethyl)amine

8-(1-(3,5-difluorophenylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

methyl 3-acetyl-5-bromo-4-hydroxybenzoate

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