Ammonia → (2S)-2-{2-[4-(3-pyridyl)phthalazin-1(2H)-on-2-yl]isonicotinoylamino}-3-(3,4-dimethoxyphenyl)-1-propanol

HRID 1739433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1739433
Br[C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][N:24]=1)[C:5]([NH:7][C@@H:8]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)[CH2:9][OH:10])=[O:6].C(=O)([O-])[O-].[K+].[K+].[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40](=[O:47])[NH:39][N:38]=2)[CH:32]=1.N>CN(C)C=O.[Cu]I>[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40](=[O:47])[N:39]([C:2]3[CH:3]=[C:4]([CH:22]=[CH:23][N:24]=3)[C:5]([NH:7][C@@H:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)[CH2:9][OH:10])=[O:6])[N:38]=2)[CH:32]=1

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 100138394-(3-pyridyl)phthalazin-1(2H)-oneHCID 57095136(2S)-2-(2-bromoisonicotinoylamino)-3-(3,4-dimethoxyphenyl)-1-propanol

Produkt 1

HCID 18393034(2S)-2-{2-[4-(3-pyridyl)phthalazin-1(2H)-on-2-yl]isonicotinoylamino}-3-(3,4-dimethoxyphenyl)-1-propanolAusbeute 20,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of (2S)-2-(2-bromoisonicotinoylamino)-3-(3,4-dimethoxyphenyl)-1-propanol (1.2 g) in dimethylformamide (40 ml) are added potassium carbonate (0.88 g) and copper (I) iodide (0.61 g) at room temperature under nitrogen atmosphere. The mixture is heated with stirring at 120° C. for 30 minutes. To the reaction mixture is added 4-(3-pyridyl)phthalazin-1(2H)-one (1.42 g), and the mixture is heated with stirring at 130° C. for two hours. The reaction mixture is cooled to room temperature, and thereto is added aqueous ammonia. The mixture is extracted with chloroform, and the extract is washed, dried and concentrated. The residue is purified by silica gel chromatography (solvent; chloroform:acetone=1:1) to give (2S)-2-{2-[4-(3-pyridyl)phthalazin-1(2H)-on-2-yl]isonicotinoylamino}-3-(3,4-dimethoxyphenyl)-1-propanol (330 mg).

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperaturethe mixture is heated
  3. stirringwith stirring at 130° C. for two hours
  4. temperatureThe reaction mixture is cooled to room temperature
  5. extractionThe mixture is extracted with chloroform
  6. washthe extract is washed
  7. customdried
  8. concentrationconcentrated
  9. customThe residue is purified by silica gel chromatography (solvent; chloroform:acetone=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-803573f5a19c4a8b9c667cbdf9d553b1
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05965730

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