Sodium Iodide → HCID 56599147, Verbindung

HRID 1750129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750129
Cl[CH2:2][C:3]#[C:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1.[Na+].[I-].Cl.[Cl:21][C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:21][C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[N:29]1[CH2:34][CH2:33][N:32]([CH2:2][C:3]#[C:4][CH2:5][O:6][C:7]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]3)=[CH:9][CH:8]=2)[CH2:31][CH2:30]1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochlorideHCID 66633798HCID 66633798, Verbindung

Produkt 1

HCID 56599147HCID 56599147, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of intermediate 50 (200 mg, 0.8 mmol) and NaI (240 mg, 1.6 mmol) in CH3CN was heated to reflux for 30 min and then cooled to rt. Intermediate 41 (320 mg, 1.2 mmol) and anhydrous K2CO3 (442 mg, 3.2 mmol) were added to the mixture. The resulting mixture was heated to reflux and stirred for 4 h. Precipitated crystals were filtered off and the filtrate was evaporated under reduced pressure. The residue was extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with DCM/MeOH=50:1) to give 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)but-2-ynyloxy)-3,4-dihydroquinolin-2(1H)-one (compound 27) (280 mg, 79%). 1H NMR (300 MHz, CDCl3): δ 7.85 (s, 1H), 7.20-7.13 (m, 2H), 7.08 (d, J=8.4 Hz, 1H), 6.97 (dd, J=3.0 Hz, 6.6 Hz, 1H), 4.73 (s, 2H), 3.42 (s, 2H), 3.10 (s, 4H), 2.93-2.88 (m, 2H), 2.75 (s, 4H), 2.64-2.59 (m, 2H), 2.06 (s, 1H), 1.70 (s, 2H), 1.29-1.24 (m, 1H). HPLC: 99%, RT 2.403 min. MS (ESI) m/z 444.1 [M+H]+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 30 min
  3. temperatureThe resulting mixture was heated
  4. temperatureto reflux
  5. customPrecipitated crystals
  6. filtrationwere filtered off
  7. customthe filtrate was evaporated under reduced pressure
  8. extractionThe residue was extracted with EtOAc
  9. washThe combined EtOAc layers were washed with brine
  10. dry with materialdried over anhydrous Na2SO4
  11. concentrationconcentrated in vacuo
  12. custompurified by flash chromatography on silica gel column (elution with DCM/MeOH=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-14b477f47db4460e8c85f2395749b78d
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156822B2

Notizen zur Reaktion

Wird geladen…