1-Bromo-2-Chloroethane → 3-[7-(2-Chloroethoxy)-1-oxoisoquinolin-2(1H)-yl]-N-cyclopropyl-4-methylbenzamide

HRID 507013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507013
[CH2:1]([NH:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][C:16]([OH:22])=[CH:17][CH:18]=3)[C:13]2=[O:23])[CH:6]=1)[CH3:2].Br[CH2:26][CH2:27][Cl:28].[C:29](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Cl:28][CH2:27][CH2:26][O:22][C:16]1[CH:15]=[C:14]2[C:19]([CH:20]=[CH:21][N:12]([C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=3[CH3:11])[C:4]([NH:3][CH:1]3[CH2:29][CH2:2]3)=[O:24])[C:13]2=[O:23])=[CH:18][CH:17]=1

Komponenten

6

Edukt 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 11674186N-Ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

Produkt 1

HCID 670185703-[7-(2-Chloroethoxy)-1-oxoisoquinolin-2(1H)-yl]-N-cyclopropyl-4-methylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-Ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide (0.65 g), 1-bromo-2-chloroethane (0.8 ml) and potassium carbonate (2.6 g) were stirred in DMF (26 ml) at 50° C. for 23 hours. The reaction mixture was diluted with ethyl acetate and washed with water (×5), brine (×2), dried (magnesium sulfate) and concentrated to give 3-[7-(2-chloroethoxy)-1-oxoisoquinolin-2(1H)-yl]-N-cyclopropyl-4-methylbenzamide as a foam (577 mg); NMR Spectrum: (DMSO d6) 1.17 (t, 3H), 2.16 (s, 3H), 3.34 (m, 2H), 4.05 (t, 2H), 4.45 (m, 2H), 6.80 (d, 1H), 7.30 (d, 1H), 7.53 (m, 2H), 7.74 (d, 1H), 7.82 (m, 2H), 7.94 (d, 1H), 8.51 (t, 1H); Mass Spectrum: M+H+ 385.

Aufarbeitung

  1. washwashed with water (×5), brine (×2)
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d52b6c39bb3c47cea5d16ec064d102a9
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786115B2

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