Sodium hydride → Isopropyl [6-[3-[4-(diphenylmethoxy) piperidino]propoxy][1,2,4]triazolo[1,5-b]pyridazin-2-yl]carboxylate

HRID 1067570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1067570
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][OH:18])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:28]1[CH:29]=[CH:30][C:31]2[N:32]([N:34]=[C:35]([C:37]([O:39][CH:40]([CH3:42])[CH3:41])=[O:38])[N:36]=2)[N:33]=1>CN(C)C=O>[C:19]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:28]3[CH:29]=[CH:30][C:31]4[N:32]([N:34]=[C:35]([C:37]([O:39][CH:40]([CH3:42])[CH3:41])=[O:38])[N:36]=4)[N:33]=3)[CH2:11][CH2:10]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 22989245Isopropyl 6-chloro[1,2,4]triazolo[1,5-b]pyridazine-2-carboxylateHCID 229892644-(Diphenylmethoxy)piperidinepropanol

Produkt 1

HCID 53847838Isopropyl [6-[3-[4-(diphenylmethoxy) piperidino]propoxy][1,2,4]triazolo[1,5-b]pyridazin-2-yl]carboxylateAusbeute 43,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

653 mg of 4-(diphenylmethoxy)-1-piperidinepropanol was dissolved in 10 ml of N,N-dimethylformamide; 88 mg of a 60% dispersion of sodium hydride in mineral oil was added, followed by stirring at room temperature under reduced pressure for 1.5 hours. To the reaction mixture, 483 mg of isopropyl (6-chloro[1,2,4]triazolo[1,5-b]pyridazin-2-yl)carboxylate was added under ice cooling conditions, followed by stirring at constant temperature for 3.5 hours. Ice water was added, followed by extraction with ethyl acetate-tetrahydrofuran (1:1); the extract was washed with saturated saline and dried with magnesium sulfate. 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 and concentrated; the crystal precipitated was washed with ethyl ether, collected by filtration and dried to yield 462 mg of the title compound.

Aufarbeitung

  1. stirringby stirring at constant temperature for 3.5 hours
  2. extractionfollowed by extraction with ethyl acetate-tetrahydrofuran (1:1)
  3. washthe extract was washed with saturated saline
  4. dry with materialdried with magnesium sulfate
  5. concentrationThe dry product was concentrated under reduced pressure
  6. washeluted with ethyl acetate:methanol (10:1)
  7. customThe desired fraction was collected
  8. concentrationconcentrated
  9. customthe crystal precipitated
  10. washwas washed with ethyl ether
  11. filtrationcollected by filtration
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b4869a49d6f04a6a9d9daaa4cf34be92
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248740B1

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