Cyclopropylamine → Methyl 3-(cyclopropylamino)-2-phenylquinoxaline-6-carboxylate

HRID 1405527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1405527
Cl[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N: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.[CH:22]1([NH2:25])[CH2:24][CH2:23]1>CS(C)=O>[CH:22]1([NH:25][C:2]2[C:3]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:4][C:5]3[C:10]([N:11]=2)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)[CH2:24][CH2:23]1

Komponenten

4

Edukt 2

HCID 69828CyclopropylamineHCID 77231183Methyl 3-chloro-2-phenylquinoxaline-6-carboxylate

Produkt 1

HCID 67042136Methyl 3-(cyclopropylamino)-2-phenylquinoxaline-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Into a 20-mL sealed tube, was placed methyl 3-chloro-2-phenylquinoxaline-6-carboxylate (200 mg, 0.67 mmol, 1.00 equiv), cyclopropanamine (10 mL), DMSO (1 mL). The resulting solution was stirred overnight at 50° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with H2O. The resulting solids were collected by filtration and applied onto a silica gel column with PE/EA (50:1). This resulted in 182.4 mg (83%) of methyl 3-(cyclopropylamino)-2-phenylquinoxaline-6-carboxylate as a yellow solid.

Aufarbeitung

  1. customInto a 20-mL sealed tube
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. additionThe resulting solution was diluted with H2O
  4. filtrationThe resulting solids were collected by filtration
  5. customThis resulted in 182.4 mg (83%) of methyl 3-(cyclopropylamino)-2-phenylquinoxaline-6-carboxylate as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-a1dcaca4d2734c46ab918500b2c92dcc
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916560B2

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