Pyridine → (S)-methyl 3-(methyl(1-phenylethyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

HRID 1403535

Reaktionsgleichung

Reaktionsgleichung von HRID 1403535
[CH3:1][N:2]([C@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19])[C:3]1[C:4](=[O:17])[NH:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=2.N1C=CC=CC=1.[O:32](S(C(F)(F)F)(=O)=O)[S:33]([C:36]([F:39])([F:38])[F:37])(=O)=[O:34]>ClCCl>[CH3:1][N:2]([C@H:18]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH3:19])[C:3]1[C:4]([O:17][S:33]([C:36]([F:39])([F:38])[F:37])(=[O:34])=[O:32])=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=2

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 70665101(S)-methyl 3-(methyl(1-phenylethyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Produkt 1

HCID 86670575(S)-methyl 3-(methyl(1-phenylethyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-methyl 3-(methyl(1-phenylethyl)amino)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (320 mg, 0.95 mmol) in dichloromethane (30 mL) was added pyridine (313 mg, 3.96 mmol), and Tf2O (559 mg, 1.98 mmol). The resulting solution was stirred overnight at room temperature and then concentrated under vacuum to get a residue, which was purified via silica gel chromatography (1% to 5% ethyl acetate in petroleum ether) to give (S)-methyl 3-(methyl(1-phenylethyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate as a yellow solid (432 mg, crude).

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. customto get a residue, which
  3. customwas purified via silica gel chromatography (1% to 5% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-9e59c543b2b8438f87893d0b1aaece6b
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912188B2

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