1H-1,2,4-Triazole → 1-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

HRID 245428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245428
C(=O)([O-])[O-].[K+].[K+].[Si:7]([O:24][CH2:25][C:26]1[C:27]([N:38]2[CH2:43][C@H:42]([CH3:44])[O:41][C@H:40]([CH3:45])[CH2:39]2)=[C:28]([F:37])[C:29]([F:36])=[C:30]([C:32](=[O:35])[CH2:33]Cl)[CH:31]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH:46]1[CH:50]=[N:49][CH:48]=[N:47]1>C(#N)C>[Si:7]([O:24][CH2:25][C:26]1[C:27]([N:38]2[CH2:43][C@H:42]([CH3:44])[O:41][C@H:40]([CH3:45])[CH2:39]2)=[C:28]([F:37])[C:29]([F:36])=[C:30]([C:32](=[O:35])[CH2:33][N:46]2[CH:50]=[N:49][CH:48]=[N:47]2)[CH:31]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 866580761-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2-chloroethanone2×

Produkt 1

HCID 866580811-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Potassium carbonate (1208 mg, 8.74 mmol) was added to a mixture of 1-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2-chloroethanone (Intermediate 127, 500 mg, 0.87 mmol) and 1H-1,2,4-triazole (66.4 mg, 0.96 mmol) dissolved in 15 ml of Acetonitrile. The mixture was stirred at room temperature for 3 hours. Potassium carbonate was filtered from the mixture, and the filtrate was diluted with water and extracted with ethyl acetate (2×100 mL). The organic phases were combined, dried (Na2SO4), and concentrated. The crude residue (482 mg, 91%) contained mainly desired title compound and was used in the next step without further purification.

Aufarbeitung

  1. filtrationPotassium carbonate was filtered from the mixture
  2. additionthe filtrate was diluted with water
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customwas used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-5e0c718e2aaf410a974386d2c7640b25
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658641B2

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