Dimethylformamide → N1-Cyclopropyl-5-[(2-{[4-(4-hydroxypiperidino)butanoyl]amino}-4-pyridyl)oxy]-1H-1-indolecarboxamide

HRID 1433458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433458
[CH:1]1([NH:4][C:5](=O)[O:6]C2C=CC=CC=2)[CH2:3][CH2:2]1.[OH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][C:24]([NH:26][C:27]2[CH:32]=[C:31]([O:33][C:34]3[CH:35]=[C:36]4[C:40](=[CH:41][CH:42]=3)[NH:39][CH:38]=[CH:37]4)[CH:30]=[CH:29][N:28]=2)=[O:25])[CH2:17][CH2:16]1.[H-].[Na+].CN(C)C=O>O>[CH:1]1([NH:4][C:5]([N:39]2[C:40]3[C:36](=[CH:35][C:34]([O:33][C:31]4[CH:30]=[CH:29][N:28]=[C:27]([NH:26][C:24](=[O:25])[CH2:23][CH2:22][CH2:21][N:18]5[CH2:17][CH2:16][CH:15]([OH:14])[CH2:20][CH2:19]5)[CH:32]=4)=[CH:42][CH:41]=3)[CH:37]=[CH:38]2)=[O:6])[CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 13648483Phenyl cyclopropylcarbamateHCID 672022485-[(2-{[4-(4-Hydroxypiperidino)butanoyl]amino}-4-pyridyl)oxy]indole

Produkt 1

HCID 58931039N1-Cyclopropyl-5-[(2-{[4-(4-hydroxypiperidino)butanoyl]amino}-4-pyridyl)oxy]-1H-1-indolecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Phenyl N-cyclopropylcarbamate (120 mg) was added to a solution of 260 mg of 5-[(2-{[4-(4-hydroxypiperidino)butanoyl]amino}-4-pyridyl)oxy]indole, 53 mg of sodium hydride (60% in oil) and 5 ml of dimethylformamide while stirring at room temperature. After stirring for 10 minutes, water was added and extraction was performed with ethyl acetate. NH type silica gel was added to the ethyl acetate layer, the solvent was distilled off under reduced pressure and the reaction product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with NH type silica gel, and purification was performed by column chromatography (chloroform:methanol=30:1). The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate and washed twice with 1N aqueous sodium hydroxide. After drying over sodium sulfate, the solvent was distilled off under reduced pressure to obtain 20 mg of the target substance as a white powder.

Aufarbeitung

  1. stirringAfter stirring for 10 minutes
  2. extractionextraction
  3. additionNH type silica gel was added to the ethyl acetate layer
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe silica gel was charged into a dry column
  6. custompacked with NH type silica gel, and purification
  7. distillationThe solvent was distilled off under reduced pressure
  8. dissolutionthe residue was dissolved in ethyl acetate
  9. washwashed twice with 1N aqueous sodium hydroxide
  10. dry with materialAfter drying over sodium sulfate
  11. distillationthe solvent was distilled off under reduced pressure
  12. customto obtain 20 mg of the target substance as a white powder

Quellen und Nachweise

ORD-Eintrag
ord-1e7a6b3458cc4e55a5de71a6adb62816
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612092B2

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