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

Hydrochloric Acid → HCID 21073767, Verbindung

HRID 1373563
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1373563
C[O:2][C:3]1[CH2:12][C:11]2[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]4[N:33]=[C:32]5[C:27]([CH:28]=[CH:29][C:30](=[O:34])[NH:31]5)=[CH:26][CH:25]=4)[CH2:15][CH2:14]3)=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH:4]=1.Cl>C(O)C.O1CCCC1>[O:2]=[C:3]1[CH2:12][C:11]2[C:10]([N:13]3[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]4[N:33]=[C:32]5[C:27]([CH:28]=[CH:29][C:30](=[O:34])[NH:31]5)=[CH:26][CH:25]=4)[CH2:17][CH2:18]3)=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 210737637-{4-[4-(7-Methoxy-5,8-dihydro-naphthalen-1-yl)-piperazin-1-yl]-butoxy}-1H-[1,8]naphthyridin-2-one

Produkt 1

HCID 21073767HCID 21073767, VerbindungAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

7-{4-[4-(7-Methoxy-5,8-dihydro-naphthalen-1-yl)-piperazin-1-yl]-butoxy}-1H-[1,8]naphthyridin-2-one (360 mg, 0.78 mmol) was dissolved in a mixture of ethanol (6 mL) and tetrahydrofuran (2 mL). To this was added 10% hydrochloric acid (1.5 mL) and the mixture was stirred at room temperature for 15 minutes, then quenched with saturated sodium bicarbonate (10 mL). The mixture was extracted with ethyl acetate (20 mL) and the organic layer was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and evaporated. The crude solid was purified by column chromatography (6:94 triethylamine/ethyl acetate) to yield the title compound (263 mg, 75%) as a white foam. 1H NMR (400 MHz, CDCl3) δ 9.15 (s, 1H), 7.76 (d, 1H), 7.60 (d, 1H), 7.20 (t, 1H), 7.00–6.95 (m, 2H), 6.60 (d, 1H), 6.50 (d, 1H), 4.40 (t, 2H), 3.60 (s, 2H), 3.04 (t, 2H), 2.90–2.80 (m, 4H), 2.80–2.40 (m, 8H), 1.90–1.60 (m, 4H), MS ES+ 447.05 (M+H)+ (Exact mass: 446.23).

Aufarbeitung

  1. customquenched with saturated sodium bicarbonate (10 mL)
  2. extractionThe mixture was extracted with ethyl acetate (20 mL)
  3. washthe organic layer was washed with brine (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude solid was purified by column chromatography (6:94 triethylamine/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e8f53c8d865647d7a8dc0416666c7d53
Quelldatensatz
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07160888B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion