Potassium Carbonate → racemic 5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-4-(hydroxymethyl)-1,3-oxazolidin-2-one

HRID 595333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595333
FC(F)(F)C([O:5][CH2:6][CH:7]1[CH:11]([CH2:12][N:13]2[CH:17]=[C:16]([C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([NH:25][C:26]4[N:31]=[C:30]([CH:32]([F:34])[F:33])[CH:29]=[CH:28][N:27]=4)[CH:19]=3)[CH:15]=[N:14]2)[O:10][C:9](=[O:35])[NH:8]1)=O.C(=O)([O-])[O-].[K+].[K+]>CO.O>[F:34][CH:32]([F:33])[C:30]1[CH:29]=[CH:28][N:27]=[C:26]([NH:25][C:20]2[CH:19]=[C:18]([C:16]3[CH:15]=[N:14][N:13]([CH2:12][CH:11]4[O:10][C:9](=[O:35])[NH:8][CH:7]4[CH2:6][OH:5])[CH:17]=3)[CH:23]=[C:22]([CH3:24])[CH:21]=2)[N:31]=1

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 118208619(5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-2-oxo-1,3-oxazolidin-4-yl)methyl trifluoroacetate

Produkt 1

HCID 118208809racemic 5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-4-(hydroxymethyl)-1,3-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of (5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-2-oxo-1,3-oxazolidin-4-yl)methyl trifluoroacetate (80 mg, 0.15 mmol) and potassium carbonate (80 mg, 0.58 mmol) in methanol (3 mL) was stirred at 25° C. for 30 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by prep-TLC (ethyl acetate) to give racemic 5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-4-(hydroxymethyl)-1,3-oxazolidin-2-one. MS ESI calc'd. for C20H21F2N6O3 [M+H]+ 431. found 431.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product residue
  6. customThe crude product residue was purified by prep-TLC (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d6559652d59d427d866bc0c3650a9b6d
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242984B2

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