Sodium Carbonate → HCID 86683268, Verbindung

HRID 1852244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852244
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:4][N:3]=1.FC(F)(F)S(O[CH2:26][CH:27]([F:29])[F:28])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([N:14]2[CH2:19][CH2:18][N:17]([CH2:26][CH:27]([F:29])[F:28])[CH2:16][CH2:15]2)=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 71742714HCID 71742714, Verbindung

Produkt 1

HCID 86683268HCID 86683268, VerbindungAusbeute 16,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-chloro-6-methoxy-4-(piperazin-1-yl)isoquinoline (0.2 g, 0.720 mmol) in DMF (5 ml) was added 2,2-Difluoroethyl trifluoromethanesulfonate (0.154 g, 0.720 mmol) followed by sodium carbonate (0.114 g, 1.080 mmol). The reaction mass was stirred until judged complete. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to get crude compound. The crude compound was purified by silica gel chromatography (10% ethyl acetate in pet ether) to get desired compound (0.04 g, 15.93%) as semi solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 8.18-8.15 (d, J=12 Hz, 1H), 7.93 (s, 1H), 7.45-7.42 (d, J=12 Hz, 1H), 7.37 (s, 1H), 6.36-5.76 (tf, 1H), 3.97 (s, 3H), 3.10 (m, 4H), 2.84 (m, 4H); 19F NMR: δ ppm −118.59 (1F); MS: MS m/z 342.19 (M++1).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto get crude compound
  6. customThe crude compound was purified by silica gel chromatography (10% ethyl acetate in pet ether)

Quellen und Nachweise

ORD-Eintrag
ord-f3fe085a3dca4bc581c59676ffa67b1f
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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