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

5-chloro-N-methoxy-8-[4-(2-methoxyethyl)piperazin-1-yl]-N-methylquinoline-7-carboxamide → 1-{5-Chloro-8-[4-(2-methoxyethyl)piperazin-1-yl]quinolin-7-yl}ethanone

HRID 1192494
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1192494
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](N(OC)C)=[O:13])[C:9]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][O:26][CH3:27])[CH2:20][CH2:19]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:28][Mg]Br>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:13])[CH3:28])[C:9]([N:18]2[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][O:26][CH3:27])[CH2:22][CH2:23]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 866561755-chloro-N-methoxy-8-[4-(2-methoxyethyl)piperazin-1-yl]-N-methylquinoline-7-carboxamideHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 673016751-{5-Chloro-8-[4-(2-methoxyethyl)piperazin-1-yl]quinolin-7-yl}ethanoneAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of 5-chloro-N-methoxy-8-[4-(2-methoxyethyl)piperazin-1-yl]-N-methylquinoline-7-carboxamide (63 mg, 0.16 mmol) in tetrahydrofuran (0.2 mL) was added 1.40 M methylmagnesium bromide in tetrahydrofuran (0.69 mL, 0.96 mmol). The reaction was stirred at room temperature overnight, quenched with saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The resultant residue was purified on silica gel, eluting with 0 to 10% MeOH in dichloromethane, to give the desired product (22 mg, 39%). LCMS calculated for C18H23ClN3O2(M+H)+: m/z=348.1; found: 348.1.

Aufarbeitung

  1. customquenched with saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe resultant residue was purified on silica gel
  7. washeluting with 0 to 10% MeOH in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-1b564da12add41de9a155ce62f300d1f
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08680108B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion