StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Phosphorus oxychloride → 9-acetyl-2-(4-ethyl-1H-imidazol-1-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

HRID 532952
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 532952
[C:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][N:8]1[C:18](=[O:19])[CH2:17][NH:16][C:15](=O)[CH:14]=[C:9]12)(=[O:3])[CH3:2].O=P(Cl)(Cl)Cl.[CH2:26]([C:28]1[N:29]=[CH:30][NH:31][CH:32]=1)[CH3:27].C([O-])(O)=O.[Na+]>ClCCCl.O>[C:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][N:8]1[C:18](=[O:19])[CH2:17][N:16]=[C:15]([N:31]3[CH:32]=[C:28]([CH2:26][CH3:27])[N:29]=[CH:30]3)[CH:14]=[C:9]12)(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 867113789-Acetyl-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dioneHCID 178437183HCID 178437183, Verbindung

Produkt 1

HCID 867113959-acetyl-2-(4-ethyl-1H-imidazol-1-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-oneAusbeute 128,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

115-1. A mixture of 9-acetyl-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione [example 100-1] (128 mg, 0.47 mmol) in DCE (4 mL) was treated with POCl3 (0.053 mL, 0.57 mmol) and heated to 110° C. for 1 h. The mixture was then allowed to cool to RT and then poured onto cooled H2O. The mixture was extracted with DCM and the combined org. phases were dried over Na2SO4, filtered and concentrated in vacuo. The residue obtained was taken up in DCE (4 mL) and 4-ethyl-1H-imidazole (182 mg, 1.89 mmol) was added. The mixture was heated to 110° C. for 1 h, then allowed to cool to rt and poured onto a saturated aq. solution of NaHCO3. The mixture was extracted with DCM and the combined org. layers were dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (210 mg) that was used as it is in the next step. UPLC-MS: MS 349.2 (M+H+); UPLC rt 0.71 min.

Aufarbeitung

  1. temperatureto cool to RT
  2. additionpoured
  3. extractionThe mixture was extracted with DCM
  4. dry with materialphases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue obtained
  8. temperatureThe mixture was heated to 110° C. for 1 h
  9. temperatureto cool to rt
  10. extractionThe mixture was extracted with DCM
  11. dry with materiallayers were dried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-44b1b85e8443404ca4332bda281206c4
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08853203B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion