Triethylamine → 5-Cyano-N-[4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]furan-2-carboxamide

HRID 1967837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1967837
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:19][C:20]([CH:22]2[CH:26]=[CH:25][C:24](=NO)[O:23]2)=[O:21])[S:9][C:10]=1[C:11]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12].[CH2:29]([N:31](CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.C(=O)([O-])O.[Na+]>ClCCl>[C:29]([C:24]1[O:23][C:22]([C:20]([NH:19][C:8]2[S:9][C:10]([C:11]([CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[O:12])=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[N:7]=2)=[O:21])=[CH:26][CH:25]=1)#[N:31]

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 516892Sodium BicarbonateHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 86612469N-[4-(2-Furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]-5-(hydroxyimino)furan-2-carboxamide

Produkt 1

HCID 231447485-Cyano-N-[4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]furan-2-carboxamideAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Compound 514 (2.08 g, 5.00 mmol) and triethylamine (0.836 mL, 6.00 mmol) were suspended in dichloromethane (20 mL), and 2-chloro-1,3-dimethylimidazolinium chloride (2.03 g, 12.0 mmol) was added thereto at 0° C. This was stirred at 0° C. for 30 minutes, and then triethylamine (0.836 mL, 6.00 mmol) was added thereto, followed by stirring at 0° C. for 5 minutes. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture, followed by extraction with chloroform. The organic layer was 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=49:1), followed by recrystallizing from a mixed solvent (3:1) of ethanol and water to afford the entitled Compound 515 (1.26 g, 63%) as a pale brown solid.

Aufarbeitung

  1. customat 0° C
  2. stirringby stirring at 0° C. for 5 minutes
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=49:1)
  7. customby recrystallizing from a mixed solvent (3:1) of ethanol and water

Quellen und Nachweise

ORD-Eintrag
ord-c829ae42981f4dcab526c9da4e9c2218
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420827B2

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