8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N-(2-hydroxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

Base Information

• Chemical Name: 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N-(2-hydroxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide
• CAS No.: 1403458-24-1
• Molecular Formula: C₂₇H₂₉F₂N₃O₅
• Molecular Weight: 513.541

Synonyms:8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N-(2-hydroxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

Chemical Property of 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N-(2-hydroxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

Chemical Property:

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Technology Process of 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N-(2-hydroxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

There total 12 articles about 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N-(2-hydroxyethyl)-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: 71.0%

(2-hydroxyethyl)(methyl)amine (109-83-1) + 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (1403458-62-7) → 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N-(2-hydroxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (1403458-24-1)

Guidance literature:

With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 16h;

Reference yield:

methyl 4-hydroxylbenzoate (99-76-3,156291-94-0) → 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N-(2-hydroxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (1403458-24-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: bromine / dichloromethane / 36 h / 0 - 20 °C / Inert atmosphere

2.1: triethylamine / palladium diacetate; 1,1'-bis(diphenylphosphino)ferrocene / ethanol / 70 °C / Inert atmosphere

3.1: bromine; pyridine / dichloromethane / 2 h / 0 - 20 °C

4.1: trifluoroborane diethyl ether / toluene / 20 °C / Inert atmosphere

4.2: 12 h / 90 °C

5.1: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,2-dimethoxyethane; water / 7 h / 80 °C / Inert atmosphere

6.1: hydrogen / 5% rhodium on activated aluminium oxide / methanol / 7 h / 65 °C / 3750.38 Torr

7.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 4 h / 20 °C

8.1: caesium carbonate / Palladium complex / 1,4-dioxane / 23 h / 80 °C / Inert atmosphere

9.1: sodium hydroxide; water / methanol / 6 h / 40 °C

9.2: 0 °C / pH 5

10.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 4-methyl-morpholine / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C

With 4-methyl-morpholine; pyridine; hydrogenchloride; water; hydrogen; bromine; trifluoroborane diethyl ether; sodium carbonate; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; sodium hydroxide; bis-triphenylphosphine-palladium(II) chloride; 1,1'-bis(diphenylphosphino)ferrocene; 5% rhodium on activated aluminium oxide; palladium diacetate; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; toluene;

Reference yield:

methyl 3-acetyl-4-hydroxybenzoate (57009-12-8) → 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N-(2-hydroxyethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (1403458-24-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: bromine; pyridine / dichloromethane / 2 h / 0 - 20 °C

2.1: trifluoroborane diethyl ether / toluene / 20 °C / Inert atmosphere

2.2: 12 h / 90 °C

3.1: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,2-dimethoxyethane; water / 7 h / 80 °C / Inert atmosphere

4.1: hydrogen / 5% rhodium on activated aluminium oxide / methanol / 7 h / 65 °C / 3750.38 Torr

5.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 4 h / 20 °C

6.1: caesium carbonate / Palladium complex / 1,4-dioxane / 23 h / 80 °C / Inert atmosphere

7.1: sodium hydroxide; water / methanol / 6 h / 40 °C

7.2: 0 °C / pH 5

8.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 4-methyl-morpholine / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C

With 4-methyl-morpholine; pyridine; hydrogenchloride; water; hydrogen; bromine; trifluoroborane diethyl ether; sodium carbonate; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; sodium hydroxide; bis-triphenylphosphine-palladium(II) chloride; 5% rhodium on activated aluminium oxide; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; 1,2-dimethoxyethane; dichloromethane; water; toluene;

upstream raw materials:

methyl 4-hydroxylbenzoate

methyl 3-bromo-4-hydroxybenzoate

(2-hydroxyethyl)(methyl)amine

8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

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