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Potassium Carbonate → N-{4-bromo-5-methyl-2-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]phenyl}acetamide

HRID 69106
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 69106
Cl.[O:2]1[CH2:7][CH2:6][CH:5]([NH:8][NH2:9])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[Br:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20]([NH:24][C:25](=[O:27])[CH3:26])=[C:19]([C:28](=O)/[CH:29]=[CH:30]/N(C)C)[CH:18]=1.O.C(OCC)(=O)C>C(O)C>[Br:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20]([NH:24][C:25](=[O:27])[CH3:26])=[C:19]([C:28]2[N:8]([CH:5]3[CH2:6][CH2:7][O:2][CH2:3][CH2:4]3)[N:9]=[CH:30][CH:29]=2)[CH:18]=1
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Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 17773358(Oxan-4-yl)hydrazine hydrochlorideHCID 22728543Water ethylacetateHCID 86694309N-{4-bromo-2-[(2E)-3-(dimethylamino)prop-2-enoyl]-5-methylphenyl}acetamide

Produkt 1

HCID 66696267N-{4-bromo-5-methyl-2-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]phenyl}acetamideAusbeute 56,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 3.37 g of tetrahydro-2H-pyran-4-ylhydrazine hydrochloride in 120 mL of ethanol was added 3.82 g of powdery potassium carbonate, followed by stirring at room temperature for 30 minutes. To a mixture was added 6 g of N-{4-bromo-2-[(2E)-3-(dimethylamino)prop-2-enoyl]-5-methylphenyl}acetamide, followed by stirring at 80° C. for 16 hours and cooling to room temperature. The mixture was poured into a mixture of water/ethyl acetate, and the aqueous layer was separated. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 3.96 g of N-{4-bromo-5-methyl-2-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]phenyl}acetamide.

Aufarbeitung

  1. stirringby stirring at 80° C. for 16 hours
  2. temperaturecooling to room temperature
  3. customthe aqueous layer was separated
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-47f6aa8a15494a88af32a108a5e08c8f
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08822448B2

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