Pyridine → (S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

HRID 1403622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1403622
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[C:8]([N:14]3[CH2:18][CH2:17][CH2:16][C@@H:15]3[CH3:19])[C:9](=[O:13])[NH:10]2)=[CH:5][C:4]=1[C:20]([O:22][CH3:23])=[O:21].N1C=CC=CC=1.[O:30](S(C(F)(F)F)(=O)=O)[S:31]([C:34]([F:37])([F:36])[F:35])(=O)=[O:32]>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[C:8]([N:14]3[CH2:18][CH2:17][CH2:16][C@@H:15]3[CH3:19])[C:9]([O:13][S:31]([C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:30])=[N:10]2)=[CH:5][C:4]=1[C:20]([O:22][CH3:23])=[O:21]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 70665330(S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

Produkt 1

HCID 86670579(S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (1.0 g, 3.15 mmol) in dichloromethane (80 ml) was added pyridine (990 mg, 12.52 mmol) and Tf2O (1.69 g, 5.99 mmol), and the reaction was stirred overnight under an atmosphere of nitrogen at room temperature. The reaction mixture was then quenched with water (200 ml), extracted with dichloromethane (3×30 mL), the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford (S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate as red oil (1.20 g, crude), which was used in the next step directly.

Aufarbeitung

  1. customThe reaction mixture was then quenched with water (200 ml)
  2. extractionextracted with dichloromethane (3×30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-05e187199bce40d19712e50bcda0dd6b
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912188B2

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