Ethanolamine → HCID 9976768, Verbindung

HRID 1866219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1866219
C(CN)O.C(=O)([O-])[O-].[K+].[K+].[F:11][C:12]1[C:20]([F:21])=[C:19]2[C:15]([C:16]([NH:30]C(=O)CCC)=[N:17][N:18]2[CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=[CH:14][C:13]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C)C=O>[F:11][C:12]1[C:20]([F:21])=[C:19]2[C:15]([C:16]([NH2:30])=[N:17][N:18]2[CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=[CH:14][C:13]=1[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Komponenten

5

Edukt 3

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 10026554HCID 10026554, Verbindung

Produkt 1

HCID 9976768HCID 9976768, VerbindungAusbeute 23,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.1 cm3 of ethanolamine and then 1.50 g of potassium carbonate are added to 1.6 g of N-[6,7-difluoro-5-phenyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]-butanamide described above, in 50 cm3 of dimethylformamide, and the mixture is refluxed for one week. The reaction medium is concentrated to dryness under reduced pressure and taken up in 150 cm3 of ethyl acetate and 75 cm3 of water. The organic phase is separated out after settling of the phases and washed successively with twice 75 cm3 of water and 50 cm3 of brine. The organic phase is dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa; 50° C.). The crude oil obtained is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 4 cm), eluting with a cyclohexane/ethyl acetate mixture (80/20 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.). After drying (90 Pa; 45° C.), 0.32 g of 6,7-difluoro-5-phenyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazole-3-amine is obtained.

Aufarbeitung

  1. temperaturethe mixture is refluxed for one week
  2. concentrationThe reaction medium is concentrated to dryness under reduced pressure
  3. customThe organic phase is separated out
  4. washwashed successively with twice 75 cm3 of water and 50 cm3 of brine
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa; 50° C.)
  8. customThe crude oil obtained
  9. customis purified by chromatography under an argon pressure of 50 kPa
  10. washon a column of silica gel (particle size 40-60 μm; diameter 4 cm), eluting with a cyclohexane/ethyl acetate mixture (80/20 by volume)
  11. additionThe fractions containing the expected product
  12. customevaporated under reduced pressure (2 kPa; 50° C.)
  13. customAfter drying (90 Pa; 45° C.)

Quellen und Nachweise

ORD-Eintrag
ord-5c4dfc4796c446e2b7711b551a888611
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629374B2

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