Ethyl 3-(3-chlorophenyl)-3-oxopropanoate → 3-(4-chlorophenyl)-7-(3-chlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-one

HRID 872084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872084
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[C:5]([NH2:14])[NH:4][N:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([C:22](=O)[CH2:23][C:24](OCC)=[O:25])[CH:19]=[CH:20][CH:21]=1>N1C=CC=CC=1>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]2[C:2]([CH3:1])=[N:3][N:4]3[C:22]([C:18]4[CH:19]=[CH:20][CH:21]=[C:16]([Cl:15])[CH:17]=4)=[CH:23][C:24](=[O:25])[NH:14][C:5]=23)=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 2757831Ethyl 3-(3-chlorophenyl)-3-oxopropanoateHCID 178434635HCID 178434635, Verbindung

Produkt 1

HCID 1363939313-(4-chlorophenyl)-7-(3-chlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-oneAusbeute 41,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

3-Methyl-4-(4-chlorophenyl)-1H-pyrazol-5-amine (578 mg) and ethyl 3-(3-chlorophenyl)-3-oxopropanoate (728 mg) are stirred overnight in a pyridine (30 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 concentrated and then 424 mg of the target compound is yielded by column chromatography. 1H NMR (CDCl3, 300 MHz) δ 9.90 (br, 1H), 7.88 (m, 1H), 7.75 (m, 1H), 7.53 (m, 1H), 7.33 (m, 5H), 3.99 (br, 1H), 2.23 (s, 3H).

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. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1b0b960c08154c4ba7d433be0f3979fe
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975264B2

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