Methanol → HCID 178428390, Verbindung

HRID 80268

Reaktionsgleichung

Reaktionsgleichung von HRID 80268
[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH2:16][CH2:15][N:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][C:22]=4[CH3:23])[C:13]3=[O:24])=[CH:8][C:7]=2F)=O)[CH2:3][CH2:2]1.CO.O.[NH2:29][NH2:30]>C(Cl)(Cl)Cl>[CH:1]1([C:4]2[C:6]3[C:7](=[CH:8][C:9]([N:12]4[CH2:16][CH2:15][N:14]([C:17]5[CH:18]=[N:19][CH:20]=[CH:21][C:22]=5[CH3:23])[C:13]4=[O:24])=[CH:10][CH:11]=3)[NH:30][N:29]=2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 596361401-(4-Cyclopropanecarbonyl-3-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

Produkt 1

HCID 178428390HCID 178428390, VerbindungAusbeute 31,97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

1-(4-Cyclopropanecarbonyl-3-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-198b: 175 mg, 0.516 mmol) in hydrazine hydrate solution (10 mL) was taken in a reaction flask. The flask was refluxed at 120° C. overnight. The reaction was monitored by TLC (5% MeOH in CHCl3). The reaction mixture was cooled to room temperature and partitioned between ice water and chloroform. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (4% MeOH in CHCl3), followed by hexane and ether wash, afforded 55 mg of the product (31.97% yield).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ice water and chloroform
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (4% MeOH in CHCl3)
  6. washwash

Quellen und Nachweise

ORD-Eintrag
ord-52b43b766cd04e2fbaf990891c972147
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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