Trimethylsilylacetylene → 1-(4-Chlorophenyl)-N-[3-ethynyl-4-(4-morpholinopiperidin-1-yl)phenyl]-5-methylpyrazole-4-carboxamide

HRID 1744643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744643
Br[C:2]1[CH:3]=[C:4]([NH:20][C:21]([C:23]2[CH:24]=[N:25][N:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[C:27]=2[CH3:28])=[O:22])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1.C[Si]([C:40]#[CH:41])(C)C>N1CCCCC1>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([N:26]2[C:27]([CH3:28])=[C:23]([C:21]([NH:20][C:4]3[CH:5]=[CH:6][C:7]([N:8]4[CH2:13][CH2:12][CH:11]([N:14]5[CH2:19][CH2:18][O:17][CH2:16][CH2:15]5)[CH2:10][CH2:9]4)=[C:2]([C:40]#[CH:41])[CH:3]=3)=[O:22])[CH:24]=[N:25]2)=[CH:30][CH:31]=1

Komponenten

4

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 22227912HCID 22227912, Verbindung

Produkt 1

HCID 222279551-(4-Chlorophenyl)-N-[3-ethynyl-4-(4-morpholinopiperidin-1-yl)phenyl]-5-methylpyrazole-4-carboxamideAusbeute 3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8082PiperidineLösungsmittel

Versuchsvorschrift

A suspension of N-[3-bromo-4-(4-morpholinopiperidin-1-yl)phenyl]-1-(4-chlorophenyl)-5-methylpyrazole-4-carboxamide (1 g), bistriphenylphosphinepalladium dichloride (0.38 g), cuprous iodide (0.06 g), trimethylsilylacetylene (0.53 g) and piperidine (50 ml) was refluxed under heating for 15 h. The solvent was evaporated and the residue was purified by silica gel column chromatography (mobile phase: ethyl acetate/hexane). The resulting residue was dissolved in methanol (10 ml) and potassium carbonate (170 mg) was added. The mixture was stirred at room temperature for 1 h. After the reaction, potassium carbonate was filtered off. The filtrate was purified by silica gel column chromatography (mobile phase: chloroform/methanol) and recrystallized from a mixed solvent of chloroform-diisopropyl ether to give the title compound (27 mg), melting point: 203–205° C.

Aufarbeitung

  1. temperaturewas refluxed
  2. temperatureunder heating for 15 h
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography (mobile phase: ethyl acetate/hexane)
  5. dissolutionThe resulting residue was dissolved in methanol (10 ml)
  6. additionpotassium carbonate (170 mg) was added
  7. customAfter the reaction, potassium carbonate
  8. filtrationwas filtered off
  9. customThe filtrate was purified by silica gel column chromatography (mobile phase: chloroform/methanol)
  10. customrecrystallized from a mixed solvent of chloroform-diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-15aab6ffd61e4a128093d67afcee3576
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015218B1

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