Potassium Hydroxide → HCID 44817769, Verbindung

HRID 885879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 885879
C([O:5][C:6](=[O:17])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][N:10]=1)(C)(C)C.[OH-].[K+].[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:28]=[C:29]([C:33](=[O:35])[CH3:34])[CH:30]=[CH:31][CH:32]=2)[CH2:23][CH2:22]1>CCO>[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:28]=[C:29]([C:33](=[O:35])/[CH:34]=[CH:15]/[C:12]3[CH:13]=[CH:14][C:9](/[CH:8]=[CH:7]/[C:6]([OH:5])=[O:17])=[N:10][CH:11]=3)[CH:30]=[CH:31][CH:32]=2)[CH2:23][CH2:22]1

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 108464921-[3-(4-Methyl-piperazin-1-YL)-phenyl]-ethanoneHCID 44819897tert-Butyl (E)-3-(5-formyl-pyridin-2-yl)-acrylate

Produkt 1

HCID 44817769HCID 44817769, VerbindungAusbeute 53,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of (E)-3-(5-formyl-pyridin-2-yl)-acrylic acid tert-butyl ester (described in Example 11 STEP A-D, 190 mg, 0.81 mmol), KOH 1.7 M (0.716 ml, 1.22 mmol) and 1-[3-(4-methyl-piperazin-1-yl)-phenyl]-ethanone (177 mg, 0.812 mmol) in EtOH (8 ml) was stirred at 0° C. for 4 h. The resulting slurry was partitioned between water and AcOEt and the organic phase was dried over Na2SO4 and evaporated in vacuo. The crude reaction mixture was purified by column chromatography (eluent: DCM/MeOH/NH4OH 98:2:0.2). The collected fractions were evaporated and the resulting powder was dissolved in DCM (10 ml) and TFA (1 ml). The solution was stirred at room temperature for 72 h. The solvent was then removed and the residue was triturated in Et2O to give 164 mg (E)-3-(5-{(E)-3-[3-(4-methyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-pyridin-2-yl)-acrylic acid as its bis-trifluoroacetate salt.

Aufarbeitung

  1. customThe resulting slurry was partitioned between water and AcOEt
  2. dry with materialthe organic phase was dried over Na2SO4
  3. customevaporated in vacuo
  4. customThe crude reaction mixture
  5. customwas purified by column chromatography (eluent: DCM/MeOH/NH4OH 98:2:0.2)
  6. customThe collected fractions were evaporated
  7. dissolutionthe resulting powder was dissolved in DCM (10 ml)
  8. stirringThe solution was stirred at room temperature for 72 h
  9. customThe solvent was then removed
  10. customthe residue was triturated in Et2O

Quellen und Nachweise

ORD-Eintrag
ord-f1cc4b57551c418681e8a1aa28dc6b6b
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242175B2

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