Potassium Iodide → 5-Amino-1-(4-fluorophenyl)-4-[3-{3-(morpholin-4-yl)propylamino}benzoyl]pyrazole

HRID 1278881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1278881
[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:26])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:22][CH2:23][CH2:24]Cl)[CH:16]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C.[Cl-].[Na+].O>[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:26])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:22][CH2:23][CH2:24][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH:16]=1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 222628035-Amino-4-[3-(3-chloropropylamino)benzoyl]-1-(4-fluorophenyl)pyrazole

Produkt 1

HCID 98885415-Amino-1-(4-fluorophenyl)-4-[3-{3-(morpholin-4-yl)propylamino}benzoyl]pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A mixture of 5-amino-4-[3-(3-chloropropylamino)benzoyl]-1-(4-fluorophenyl)-pyrazole (0.05 g, 0.13 mmol), morpholine (0.1 ml, 1.1 mmol), potassium carbonate (0.1 g) and potassium iodide (0.1 g) in acetonitrile (3 ml) was heated at reflux. After 2 days, the reaction mixture was poured into brine and the product was extracted into ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (elution gradient: 3% MeOH/CH2Cl2) to give 5-amino-1-(4-fluorophenyl)-4-[3-{3-(morpholin-4-yl)propylamino}-benzoyl]pyrazole as a solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux
  3. extractionthe product was extracted into ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (elution gradient: 3% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-aff8f12ad855499585ae9ad325fd2bb4
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06444696B1

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