Sodium Iodide → HCID 56597092, Verbindung

HRID 1750137Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750137
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:27]=[C:26]3[C:22](C=NN3)=[CH:21][CH:20]=2)[CH2:11][CH2:10]1.[Na+].[I-].Cl.Cl[C:32]1C(Cl)=CC=C[C:33]=1[N:39]1[CH2:44]CNCC1.C([O-])([O-])=[O:46].[K+].[K+]>CC#N>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:27]=[C:26]3[C:22]([CH2:32][CH2:33][NH:39][C:44]3=[O:46])=[CH:21][CH:20]=2)[CH2:13][CH2:14]1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochlorideHCID 565979396-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propoxy)-1H-indazole

Produkt 1

HCID 56597092HCID 56597092, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of intermediate 20 (110 mg, 0.39 mmol) and NaI (117 mg, 0.78 mmol) in CH3CN was heated to reflux for 30 min and then cooled to rt. Intermediate 41 (157 mg, 0.59 mmol) and anhydrous K2CO3 (216 mg, 1.56 mmol) were added to the mixture. The resulting mixture was heated to reflux and stirred for 6 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=30:1) to give 7-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propoxy)-3,4-dihydroisoquinolin-1(2H)-one (compound 32) (88 mg, 52%). 1H NMR (300 MHz, CDCl3): δ 7.61 (s, 1H), 7.14-7.11 (m, 3H), 7.03-6.98 (m, 2H), 5.93 (brs, 1H), 4.11 (m, 2H), 3.55 (m, 2H), 3.09-2.94 (m, 6H), 2.65-2.61 (m, 6H), 2.02 (s, 2H). HPLC: 99%, RT 2.612 min. MS (ESI) m/z 434.1 [M+H]+. mp: 162-164° C.

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=30:1)

Quellen und Nachweise

ORD-Eintrag
ord-5864891f8a044c8ca34f406acc116c17
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156822B2

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