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Dichloromethane → N-[(4-chlorophenyl)methyl]-1-(2-methoxyethoxymethyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 1068031
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1068031
ClC1C=CC(C[C:7]2[C:16]([C:17]([NH2:19])=[O:18])=[C:15]([OH:20])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:13]=3)[N:8]=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:36][O:37][CH2:38][CH2:39][O:40][CH2:41]Cl.Cl[CH2:44][Cl:45]>CN(C=O)C>[Cl:45][C:44]1[CH:14]=[CH:13][C:12]([CH2:21][NH:19][C:17]([C:16]2[C:15](=[O:20])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([CH2:21][N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[CH:13]=3)[N:8]([CH2:41][O:40][CH2:39][CH2:38][O:37][CH3:36])[CH:7]=2)=[O:18])=[CH:11][CH:10]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 178513551HCID 178513551, Verbindung

Produkt 1

HCID 16073911N-[(4-chlorophenyl)methyl]-1-(2-methoxyethoxymethyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of N-(4-chlorobenzyl-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (0.21 gm) from Preparation No. 40 and cesium carbonate (0.34 gm) in DMF (2 mL) is treated with 2-methoxyethoxymethyl chloride (0.07 mL). The mixture is tightly capped and heated to 100° C. for 3 hrs. The reaction mixture is allowed to cool to room temperature, diluted with dichloromethane and washed with water. The aqueous phase is extracted with two additional portions of dichloromethane. The combined organic phase is washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 1% to 5% methanol in dichloromethane and then by recrystallization with acetonitrile to afford 0.08 gm of the title compound as a white solid.

Aufarbeitung

  1. customfrom Preparation No
  2. customThe mixture is tightly capped
  3. temperatureto cool to room temperature
  4. washwashed with water
  5. extractionThe aqueous phase is extracted with two additional portions of dichloromethane
  6. washThe combined organic phase is washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product is purified by flash column chromatography
  10. washeluting with 1% to 5% methanol in dichloromethane
  11. customby recrystallization with acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-1f30f98ef84040279c17b872b2a3f157
Quelldatensatz
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06248739B1

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