Sodium Carbonate → N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-ethyl-butyramide

HRID 1927592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927592
[CH2:1]([CH:3]([CH2:20][CH3:21])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[C:9]([F:19])[CH:8]=1)=[O:5])[CH3:2].Br[CH:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:25].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=O>[NH3:6].[CH2:29]([N:26]([CH2:27][CH3:28])[C:24]([CH:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[N:16]1[CH2:15][CH2:14][N:13]([C:10]2[CH:11]=[CH:12][C:7]([NH:6][C:4](=[O:5])[CH:3]([CH2:1][CH3:2])[CH2:20][CH3:21])=[CH:8][C:9]=2[F:19])[CH2:18][CH2:17]1)=[O:25])[CH3:30]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 14897375HCID 14897375, VerbindungHCID 58870794HCID 58870794, Verbindung

Produkt 2

HCID 222AmmoniaHCID 16666511N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-ethyl-butyramideAusbeute 88,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-ethyl-N-(3-fluoro-4-piperazin-1-yl-phenyl)-butyramide (0.030 g, 0.084 mmol), 2-bromo-N,N-diethyl-2-phenyl-acetamide (0.025 g, 0.094 mmol), and Na2CO3 (0.013 g, 0.12 mmol) in DMF (2 mL) was stirred at rt for 18 h. The reaction mixture was diluted with EtOAc (25 mL) and washed with H2O (3×15 mL). The organic layer was dried (Na2SO4) and concentrated. Chromatography of the resulting residue (SiO2; 2 M NH3 in MeOH/DCM) gave the title compound (0.018 g, 38%). MS (ESI): mass calcd. for C28H39FN4O2, 482.31. m/z found, 483.5 [M+H]+. 1H NMR (CDCl3): 7.53-7.45 (m, 3H), 7.38-7.31 (m, 3H), 7.10-7.07 (m, 1H), 6.89-6.84 (m, 1H), 3.50-3.37 (m, 2H), 3.30-3.15 (m, 2H), 3.08 (s, 4H), 2.70 (br s, 4H), 2.05-2.01 (m, 1H), 1.75-1.68 (m, 2H), 1.60-1.52 (m, 2H), 1.09-1.02 (m, 6H), 0.97-0.91 (m, 6H).

Aufarbeitung

  1. washwashed with H2O (3×15 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-60ee2d781f204c6abbda739939fe1448
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183239B2

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