Potassium Carbonate → HCID 16667233, Verbindung

HRID 1927603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927603
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:36])[CH:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:24][O:25][C:26](=[O:36])[CH:27]([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)[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 57495616Methyl 2-bromo-2-(3-fluorophenyl)acetateHCID 693036372-ethyl-N-(3-fluoro-4-piperazin-1-yl-phenyl)-butyramide dihydrochloride

Produkt 1

HCID 16667233HCID 16667233, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-ethyl-N-(3-fluoro-4-piperazin-1-yl-phenyl)-butyramide dihydrochloride (0.26 g, 0.70 mmol), bromo-(3-fluoro-phenyl)-acetic acid methyl ester (0.23 g, 0.91 mmol), and anhydrous K2CO3 (0.34 g, 2.45 mmol) in DMF (10 mL) was stirred for 20 h. The mixture was diluted with water (100 mL) and extracted with DCM (2×30 mL). The combined organic layers were washed with water, dried (Na2SO4), and concentrated. The residue was purified (SiO2; acetone/DCM) to give the title compound (0.25 g, 78%). MS: mass calcd. for C25H31F2N3O3, 459.23. m/z found, 460.3 [M+H]+. 1H NMR (CDCl3): 7.48-7.43 (m, 1H), 7.35-7.28 (m, 1H), 7.25-7.20 (m, 2H), 7.17 (br s, 1H), 7.12-7.07 (m, 1H), 7.05-6.99 (m, 1H), 6.86 (t, J=9.0, 1H), 4.07 (s, 1H), 3.71 (s, 3H), 3.11-3.04 (m, 4H), 2.70-2.59 (m, 4H), 2.03-1.95 (m, 1H), 1.75-1.66 (m, 2H), 1.59-1.49 (m, 2H), 0.93 (t, J=7.4, 6H).

Aufarbeitung

  1. extractionextracted with DCM (2×30 mL)
  2. washThe combined organic layers 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-e2485cab2e3b41b49ef22254764f1a3d
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183239B2

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