1-(3-Aminopropyl)-4-methylpiperazine → 4-(3-Chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid [3-(4-methylpiperazine-yl)-propyl] amide

HRID 24607

Reaktionsgleichung

Reaktionsgleichung von HRID 24607
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([OH:16])=O)=[C:12]([CH3:17])[NH:11][C:10](=[O:18])[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[NH2:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[CH3:29][N:26]1[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][CH2:20][NH:19][C:14]([C:13]2[CH:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[NH:9][C:10](=[O:18])[NH:11][C:12]=2[CH3:17])=[O:16])[CH2:24][CH2:25]1

Komponenten

5

Edukt 3

HCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 225701824-(3-Chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid

Produkt 1

HCID 207589024-(3-Chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid [3-(4-methylpiperazine-yl)-propyl] amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

225 mg (0.844 mmol) of 4-(3-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid and 159 mg (1.01 mmol) of 1-(aminopropyl)-4-methylpiperazine were dissolved in 10 ml of DMF. 243 mg (1.27 mmol) of WSC hydrochloride was added to the obtained solution under cooling with ice, and they were stirred at room temperature overnight. After the concentration under reduced pressure, the reaction mixture was diluted with ethyl acetate and then washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (dichloromethane/methanol=50/1 to 10/1) to obtain the title compound.

Aufarbeitung

  1. temperatureunder cooling with ice, and they
  2. concentrationAfter the concentration under reduced pressure
  3. additionthe reaction mixture was diluted with ethyl acetate
  4. washwashed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by the silica gel chromatography (dichloromethane/methanol=50/1 to 10/1)

Quellen und Nachweise

ORD-Eintrag
ord-43a26fce5115473aaedeff801c5e72dd
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855716B2

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