1-Bromo-3-chloropropane → 5-Amino-4-[3-(3-chloropropylamino)benzoyl]-1-(4-fluorophenyl)pyrazole

HRID 429374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 429374
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1.Br[CH2:24][CH2:25][CH2:26][Cl:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:24][CH2:25][CH2:26][Cl:27])[CH:16]=1

Komponenten

6

Edukt 3

HCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 222628105-Amino4-(3-aminobenzoyl)-1-(4-fluorophenyl)pyrazole

Produkt 1

HCID 222628035-Amino-4-[3-(3-chloropropylamino)benzoyl]-1-(4-fluorophenyl)pyrazoleAusbeute 33,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-amino-4-(3-aminobenzoyl)-1-(4-fluorophenyl)pyrazole (0.5 g, 1.6 mmol), 1-bromo-3-chloropropane (0.26 g, 1.6 mmol) and cesium carbonate (0.52 g, 1.6 mmol) in dimethylformamide (25 ml) was heated at 80° C. After 2 days, the reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (elution gradient: 20% acetone/hexanes) to give 5-amino-4-[3-(3-chloropropylamino)benzoyl]-1-(4-fluorophenyl)pyrazole (0.2 g) as a solid.

Aufarbeitung

  1. washThe organic layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (elution gradient: 20% acetone/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9566262071704cd5bb3bf67d3d3ebe85
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316466B1

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