Ethyl 3-oxo-3-[3-(trifluoromethyl)phenyl]propanoate → 3-(4-methoxyphenyl)-7-(3-(trifluoromethyl)phenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-one

HRID 872107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872107
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[C:5]([NH2:15])[NH:4][N:3]=1.[F:16][C:17]([F:33])([F:32])[C:18]1[CH:19]=[C:20]([C:24](=O)[CH2:25][C:26](OCC)=[O:27])[CH:21]=[CH:22][CH:23]=1>N1C=CC=CC=1>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]2[C:2]([CH3:1])=[N:3][N:4]3[C:24]([C:20]4[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:32])([F:33])[F:16])[CH:19]=4)=[CH:25][C:26](=[O:27])[NH:15][C:5]=23)=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 2063905Ethyl 3-oxo-3-[3-(trifluoromethyl)phenyl]propanoateHCID 178488690HCID 178488690, Verbindung

Produkt 1

HCID 1363938973-(4-methoxyphenyl)-7-(3-(trifluoromethyl)phenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-oneAusbeute 68,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

3-Methyl-4-(4-methoxyphenyl)-1H-pyrazol-5-amine (200 mg) and ethyl 3-(3-(trifluoromethyl)phenyl)-3-oxopropanoate (307 mg) are stirred overnight in a pyridine (10 mL) solvent at 95° C. After cooling to room temperature, the reaction solvent is removed by distillation under reduced pressure. The remainder is extracted with ethyl acetate and water. The extracted organic layer is washed with brine and dehydrated with anhydrous MgSO4. The dehydrated organic layer is distilled under reduced pressure and purified by column chromatography to yield 270 mg of the target compound.

Aufarbeitung

  1. customthe reaction solvent is removed by distillation under reduced pressure
  2. extractionThe remainder is extracted with ethyl acetate and water
  3. washThe extracted organic layer is washed with brine
  4. distillationThe dehydrated organic layer is distilled under reduced pressure
  5. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d7bccee0684041959994b4cf654967f9
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975264B2

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