8-(1-(3-fluoro-5-methoxyphenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

Base Information

Chemical Name:8-(1-(3-fluoro-5-methoxyphenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide
CAS No.:1296270-70-6
Molecular Formula:C₂₅H₂₈FN₃O₅
Molecular Weight:469.513
Hs Code.:

Synonyms:

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Chemical Property of 8-(1-(3-fluoro-5-methoxyphenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

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Technology Process of 8-(1-(3-fluoro-5-methoxyphenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

There total 12 articles about 8-(1-(3-fluoro-5-methoxyphenylamino)ethyl)-N,N-dimethyl-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: 63.0%

: 2339-58-4
3-fluoro-5-methoxyphenylamine

: 1296271-50-5
8-(1-bromoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

: 1296270-70-6
8-(1-(3-fluoro-5-methoxyphenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

Guidance literature:: In N,N-dimethyl-formamide; at 50 ℃; for 5h; Inert atmosphere;
DOI:10.1021/jm501629p

Reference yield:

: 160753-84-4
methyl 3-acetyl-5-bromo-4-hydroxybenzoate

: 1296270-70-6
8-(1-(3-fluoro-5-methoxyphenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

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: sodium hydroxide; water / methanol / 1.25 h / -15 - 25 °C / Inert atmosphere

5.1: O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / 25 °C / Inert atmosphere

5.2: 0.5 h / Inert atmosphere

6.1: phosphorus tribromide / dichloromethane / 96 h / 25 °C / Inert atmosphere

7.1: N,N-dimethyl-formamide / 5 h / 50 °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; sodium hydroxide; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 2.1: |Stille Cross Coupling / 2.2: |Stille Cross Coupling;
DOI:10.1021/jm501629p

Reference yield:

: 29415-97-2
methyl 3-bromo-4-hydroxybenzoate

: 1296270-70-6
8-(1-(3-fluoro-5-methoxyphenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

Guidance literature:: Multi-step reaction with 10 steps

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

1.2: 2 h / 25 °C

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

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -65 - 0 °C / Inert atmosphere

3.2: 2 h / -65 - 25 °C / Inert atmosphere

4.1: trifluoromethylsulfonic anhydride / 1,2-dichloro-ethane / 18 h / 25 - 50 °C / Inert atmosphere

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

5.2: 0.5 h / 45 °C / Inert atmosphere

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

7.1: sodium hydroxide; water / methanol / 1.25 h / -15 - 25 °C / Inert atmosphere

8.1: O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / 25 °C / Inert atmosphere

8.2: 0.5 h / Inert atmosphere

9.1: phosphorus tribromide / dichloromethane / 96 h / 25 °C / Inert atmosphere

10.1: N,N-dimethyl-formamide / 5 h / 50 °C / Inert atmosphere

With pyridine; bis-triphenylphosphine-palladium(II) chloride; 1,1'-bis-(diphenylphosphino)ferrocene; sodium tetrahydroborate; trifluoromethylsulfonic anhydride; water; bromine; palladium diacetate; phosphorus tribromide; O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: |Heck Reaction / 1.2: |Heck Reaction / 5.1: |Stille Cross Coupling / 5.2: |Stille Cross Coupling;
DOI:10.1021/jm501629p