Diisopropylethylamine → (S)-methyl 3-(methyl(1-phenylethyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403534

Reaktionsgleichung

Reaktionsgleichung von HRID 1403534
Cl[C:2]1[C:3](=[O:16])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.CCN(C(C)C)C(C)C.[CH3:26][NH:27][C@H:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:29]>CS(C)=O>[CH3:26][N:27]([C@H:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:29])[C:2]1[C:3](=[O:16])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2060073(S)-(-)-N,alpha-DimethylbenzylamineHCID 68194304Methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Produkt 1

HCID 70665101(S)-methyl 3-(methyl(1-phenylethyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (300 mg, 1.26 mmol) in DMSO (2 mL) was added DIEA (244 mg, 1.89 mmol), and (S)—N-methyl-1-phenylethanamine (204 mg, 1.51 mmol) with stirring for 3 h at 85° C. in an oil bath. The reaction was then quenched by the addition of water (50 mL). The product was precipitated via the addition of water and collected by filtration to give (S)-methyl 3-(methyl(1-phenylethyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a gray solid (323 mg, 76%).

Aufarbeitung

  1. customThe reaction was then quenched by the addition of water (50 mL)
  2. customThe product was precipitated via the addition of water
  3. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-3702cf14e452483791e5b55a8a460e36
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912188B2

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