3-Phenylpropylamine → 6-(2-Chloroethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3-phenylpropyl)amide

HRID 24603

Reaktionsgleichung

Reaktionsgleichung von HRID 24603
[Cl:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[NH:11][C:10](=[O:12])[NH:9][CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[C:7]=1[C:20]([OH:22])=O.[C:23]1([CH2:29][CH2:30][CH2:31][NH2:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN=C=NCCCN(C)C.Cl>ClCCl>[C:23]1([CH2:29][CH2:30][CH2:31][NH:32][C:20]([C:7]2[CH:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[NH:9][C:10](=[O:12])[NH:11][C:6]=2[CH2:5][O:4][CH2:3][CH2:2][Cl:1])=[O:22])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 162593-PhenylpropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 225701406-(2-Chloroethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid

Produkt 1

HCID 207588826-(2-Chloroethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3-phenylpropyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

205 mg (0.594 mmol) of 6-(2-chloroethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid and 96.4 mg (0.713 mmol) of 3-phenylpropylamine were dissolved in 10 ml of dichloromethane. 171 mg (0.891 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 1 N hydrochloric acid, 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 30/1) 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 1 N hydrochloric acid, 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 30/1)

Quellen und Nachweise

ORD-Eintrag
ord-550d22d2b7e842f88e8b9a9e3756aa41
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855716B2

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