Potassium Carbonate → HCID 16667280, Verbindung

HRID 1927605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927605
Cl.Cl.[CH2:3]([CH:5]([CH2:22][CH3:23])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[C:11]([F:21])[CH:10]=1)=[O:7])[CH3:4].[CH3:24][O:25][C:26](=[O:37])[CH:27](Br)[C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:24][O:25][C:26](=[O:37])[CH:27]([C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1)[N:18]1[CH2:17][CH2:16][N:15]([C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[CH:5]([CH2:3][CH3:4])[CH2:22][CH3:23])=[CH:10][C:11]=2[F:21])[CH2:20][CH2:19]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 4625673Methyl 2-bromo-2-(4'-cyanophenyl)acetateHCID 693036372-ethyl-N-(3-fluoro-4-piperazin-1-yl-phenyl)-butyramide dihydrochloride

Produkt 1

HCID 16667280HCID 16667280, VerbindungAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-ethyl-N-(3-fluoro-4-piperazin-1-yl-phenyl)-butyramide dihydrochloride (0.06 g, 0.16 mmol), bromo-(4-cyano-phenyl)-acetic acid methyl ester (0.05 g, 0.20 mmol), and anhydrous K2CO3 (0.08 g, 0.55 mmol) in DMF (5 mL) was stirred at rt for 20 h. The mixture was diluted with water (100 mL) and extracted with DCM (2×30 mL). The combined organic phases were washed with water, dried (Na2SO4), and concentrated. The residue was purified (SiO2; acetone/DCM) to give the title compound (0.06 g, 79%). MS: mass calcd. for C26H31FN4O3, 466.24. m/z found, 467.4 [M+H]+. 1H NMR (CDCl3): 7.68-7.60 (m, 4H), 7.45 (dd, J=14.0, 2.4, 1H), 7.27 (br s, 1H), 7.13-7.08 (m, 1H), 6.85 (t, J=9.0, 1H), 4.14 (s, 1H), 3.72 (s, 3H), 3.10-3.03 (m, 4H), 2.69-2.56 (m, 4H), 2.04-1.95 (m, 1H), 1.74-1.62 (m, 2H), 1.59-1.48 (m, 2H), 0.92 (t, J=7.4, 6H).

Aufarbeitung

  1. extractionextracted with DCM (2×30 mL)
  2. washThe combined organic phases were washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified (SiO2; acetone/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-b0613245750d4f0c882c1d91c9252f1a
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183239B2

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