Sodium hydride → 6-[2-[2-[4-(Diphenylmethyl)piperazino] ethoxy]ethoxy]-7-isopropyl[1,2,4]triazolo[1,5-b]pyridazine

HRID 1067518

Reaktionsgleichung

Reaktionsgleichung von HRID 1067518
[H-].[Na+].[C:3]1([CH:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][OH:21])[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:29]1[C:30]([CH:38]([CH3:40])[CH3:39])=[CH:31][C:32]2[N:33]([N:35]=[CH:36][N:37]=2)[N:34]=1>O1CCCC1>[C:22]1([CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][C:29]3[C:30]([CH:38]([CH3:40])[CH3:39])=[CH:31][C:32]4[N:33]([N:35]=[CH:36][N:37]=4)[N:34]=3)[CH2:14][CH2:15]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 71135DecloxizineHCID 229892276-Chloro-7-isopropyl[1,2,4]triazolo[1,5-b]pyridazine

Produkt 1

HCID 229892836-[2-[2-[4-(Diphenylmethyl)piperazino] ethoxy]ethoxy]-7-isopropyl[1,2,4]triazolo[1,5-b]pyridazineAusbeute 50,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

160 mg of 60% sodium hydride in oil was suspended in 20 ml of tetrahydrofuran; 1.20 g of 4-(diphenylmethyl)-1-[2-(2-hydroxyethoxy)ethyl]piperazine was added, followed by heating and refluxing for 1 hour. After cooling, 610 mg of 6-chloro-7-isopropyl[1,2,4]triazolo[1,5-b]pyridazine was added, followed by heating and refluxing for 1 hour. After cooling, ice water was added, followed by extraction with ethyl acetate; the extract was washed with saturated saline and dried with magnesium sulfate. After the dry product was concentrated under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol (10:1). The desired fraction was collected; the crystal precipitated was collected by filtration, washed with ethyl ether and dried to yield 790 mg of the title compound.

Aufarbeitung

  1. temperatureby heating
  2. temperaturerefluxing for 1 hour
  3. temperatureAfter cooling
  4. temperatureby heating
  5. temperaturerefluxing for 1 hour
  6. temperatureAfter cooling
  7. extractionfollowed by extraction with ethyl acetate
  8. washthe extract was washed with saturated saline
  9. dry with materialdried with magnesium sulfate
  10. concentrationAfter the dry product was concentrated under reduced pressure
  11. washeluted with ethyl acetate:methanol (10:1)
  12. customThe desired fraction was collected
  13. customthe crystal precipitated
  14. filtrationwas collected by filtration
  15. washwashed with ethyl ether
  16. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ef8602045b2f469eaa20233b91283dd4
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248740B1

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