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1-Methylpiperazine → 3-Pyridinecarboxamide,n-[4-(2-furanyl)-5-(4-morpholinyl)-2-thiazolyl]-6-(4-methyl-1-piperazinyl)-

HRID 337407
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 337407
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[S:12][C:13]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[C:14]([C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[O:9])=[CH:4][N:3]=1.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>O1CCOCC1>[O:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[C:14]1[N:15]=[C:11]([NH:10][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:31]3[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]3)=[N:3][CH:4]=2)=[O:9])[S:12][C:13]=1[N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1
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Komponenten

4

Edukt 2

HCID 531671-MethylpiperazineHCID 231444172-Chloro-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]pyridine-5-carboxamide

Produkt 1

HCID 231441133-Pyridinecarboxamide,n-[4-(2-furanyl)-5-(4-morpholinyl)-2-thiazolyl]-6-(4-methyl-1-piperazinyl)-Ausbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Compound 32 (391 mg, 1.00 mmol) was dissolved in 1,4-dioxane (10 mL), and 1-methylpiperazine (0.56 mL, 5.00 mmol) was added thereto, followed by stirring under heating and reflux for 10 hours. The reaction mixture was concentrated under reduced pressure, a saturated aqueous solution of sodium chloride was added to the resulting residue, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=10:1:1) to afford the entitled Compound 35 (454 mg, 100%).

Aufarbeitung

  1. temperatureunder heating
  2. temperaturereflux for 10 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiona saturated aqueous solution of sodium chloride was added to the resulting residue
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled away under reduced pressure
  9. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol:28% aqueous ammonia=10:1:1)

Quellen und Nachweise

ORD-Eintrag
ord-59606d7934d24b828c053aa8547d0b75
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08889718B2

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