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

HRID 1067512

Reaktionsgleichung

Reaktionsgleichung von HRID 1067512
[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:28][C:29]1[CH:30]=[CH:31][C:32]2[N:33]([N:35]=[CH:36][N:37]=2)[N:34]=1>O1CCCC1>[ClH:28].[ClH:28].[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[CH:30]=[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 112406116-Chloro-(1,2,4)triazolo(1,5-b)pyridazine

Produkt 1

HCID 229894146-[2-[2-[4-(Diphenylmethyl)piperazino]ethoxy] ethoxy][1,2,4]triazolo[1,5-b]pyridazine dihydrochlorideAusbeute 157 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

100 mg of 60% sodium hydride in oil was suspended in 20 ml of tetrahydrofuran; 470 mg of 4-(diphenylmethyl)-1-[2-(2-hydroxyethoxy)ethyl]piperazine was added, followed by heating and refluxing for 1 hour. After cooling, 200 mg of 6-chloro[1,2,4]triazolo[1,5-b]pyridazine was added, followed by heating and refluxing for 4.5 hours. 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 dichloromethane-ethyl acetate-methanol (10:10:1). The desired fraction was collected and dissolved in 5 ml of ethyl acetate; 0.83 ml of a 4 N hydrogen chloride solution in ethyl acetate was added; the crystal precipitated was collected by filtration, washed with ethyl ether and dried to yield 0.54 g of the title compound.

Aufarbeitung

  1. temperatureby heating
  2. temperaturerefluxing for 1 hour
  3. temperatureAfter cooling
  4. temperatureby heating
  5. temperaturerefluxing for 4.5 hours
  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 dichloromethane-ethyl acetate-methanol (10:10:1)
  12. customThe desired fraction was collected
  13. dissolutiondissolved in 5 ml of ethyl acetate
  14. addition0.83 ml of a 4 N hydrogen chloride solution in ethyl acetate was added
  15. customthe crystal precipitated
  16. filtrationwas collected by filtration
  17. washwashed with ethyl ether
  18. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d09406e9a40245e086862f96d16a6045
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248740B1

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