Salicylaldehyde oxime → HCID 58072349, Verbindung

HRID 1624816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1624816
C(=NO)C1C(=CC=CC=1)O.C([O-])([O-])=O.[Cs+].[Cs+].[NH:17]1[C:21]([C:22]2[C:27](=[O:28])[CH:26]=[CH:25][N:24]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=3)[N:23]=2)=[CH:20][CH:19]=[N:18]1.I[C:40]1[CH:44]=[CH:43][S:42][CH:41]=1>CC#N.CCOC(C)=O.O.[Cu-]=O>[S:42]1[CH:43]=[CH:44][C:40]([N:17]2[C:21]([C:22]3[C:27](=[O:28])[CH:26]=[CH:25][N:24]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:37])([F:36])[F:38])[CH:30]=4)[N:23]=3)=[CH:20][CH:19]=[N:18]2)=[CH:41]1

Komponenten

9

Edukt 4

HCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 663323-IodothiopheneHCID 594361503-(1H-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one

Produkt 1

HCID 58072349HCID 58072349, VerbindungAusbeute 2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178419072HCID 178419072, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a mixture of copper (I) oxide (0.028 g, 0.20 mmol), salicylaldoxime (0.11 g, 0.78 mmol), Cs2CO3 (0.64 g, 2.0 mmol) and 3-(1H-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.30 g, 0.98 mmol) in MeCN (8 mL) was added 3-iodothiophene (0.15 mL, 1.5 mmol), and the mixture was stirred at 90° C. for 2 days and at room temperature for 4 days. The mixture was diluted with AcOEt and water, and filtered. The filtrate was partitioned between AcOEt and water. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel (20/80-100/0 AcOEt/hexane) to give yellow crystals. The crystals were purified by preparative HPLC and recrystallized from AcOEt/hexane to give the title compound (7 mg, 2% yield) as off-white crystals: 1H NMR (300 MHz, CDCl3): δ ppm 6.75 (1H, d, J=7.9 Hz), 7.12 (1H, dd, J=4.5, 1.9 Hz), 7.24 (1H, s), 7.30-7.34 (2H, m), 7.36 (1H, d, J=1.9 Hz), 7.41 (1H, s), 7.50-7.57 (1H, m), 7.59-7.64 (1H, m), 7.78 (1H, d, J=1.9 Hz), 8.23 (1H, d, J=7.9 Hz). LC-MS (ESI) m/z 389 [M+H]+.

Aufarbeitung

  1. filtrationfiltered
  2. customThe filtrate was partitioned between AcOEt and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on silica gel (20/80-100/0 AcOEt/hexane)
  8. customto give yellow crystals
  9. customThe crystals were purified by preparative HPLC
  10. customrecrystallized from AcOEt/hexane

Quellen und Nachweise

ORD-Eintrag
ord-2c0a15752e9e48bfaac0e03dabc6b2a3
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778944B2

Notizen zur Reaktion

Wird geladen…