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Methanol → HCID 57940632, Verbindung

HRID 1437309
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1437309
C[Si]([N+:5]#[C-:6])(C)C.[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([N:15]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:18][C:17]([C:26]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]3)=[O:27])=[N:16]2)=[CH:11][CH:10]=1.C[OH:35]>O1CCOCC1>[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([N:15]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:18][C:17]([C:26]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][N:29]3[C:6]([NH2:5])=[O:35])=[O:27])=[N:16]2)=[CH:11][CH:10]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 887MethanolHCID 11674985HCID 11674985, VerbindungHCID 22648882Isocyano(trimethyl)silane

Produkt 1

HCID 57940632HCID 57940632, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Trimethylsilyl isocyanide (0.920 mL) was added to 1-[1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)pyrazole-3-carbonyl]hexahydropyridazine (0.397 g) obtained in Example 162 in 1,4-dioxane (3 mL) at room temperature, followed by stirring at an external temperature of 110° C. in a sealed tube for 4 days. Subsequently, the mixture was cooled in air. After methanol was added to the reaction mixture, the reaction solvent was removed under reduced pressure. The residue was partitioned between saturated aqueous solution of sodium hydrogencarbonate and a mixture solvent of chloroform-methanol (20:1). The organic layer was washed with saturated brine, and then dried over sodium sulfate anhydrate. The mixture was subjected to filtration, and the solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give the title compound as a solid (0.122 g, 25%).

Aufarbeitung

  1. temperatureSubsequently, the mixture was cooled in air
  2. customthe reaction solvent was removed under reduced pressure
  3. customThe residue was partitioned between saturated aqueous solution of sodium hydrogencarbonate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate anhydrate
  6. filtrationThe mixture was subjected to filtration
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified through silica gel column chromatography (chloroform-methanol)

Quellen und Nachweise

ORD-Eintrag
ord-2eacf359db1f49d48b10dfeeca5b897b
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07622471B2

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