Ethyl 6-chloro-α,α-dimethylimidazo[1,2-b]pyridazine-2-acetate → Ethyl 2-[6-[3-[4-(Diphenylmethoxy)piperidino]-2-hydroxypropylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate Difumarate

HRID 1067521

Reaktionsgleichung

Reaktionsgleichung von HRID 1067521
[C:1]1([CH:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH:16]([OH:19])[CH2:17][NH2:18])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:27]1[CH:28]=[CH:29][C:30]2[N:31]([CH:33]=[C:34]([C:36]([CH3:43])([CH3:42])[C:37]([O:39][CH2:40][CH3:41])=[O:38])[N:35]=2)[N:32]=1.[C:44]([O:47]CC)(=[O:46])[CH3:45].O1CCCC1>>[C:37]([OH:39])(=[O:38])/[CH:36]=[CH:45]/[C:44]([OH:47])=[O:46].[C:37]([OH:39])(=[O:38])/[CH:36]=[CH:45]/[C:44]([OH:47])=[O:46].[C:20]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][CH:16]([OH:19])[CH2:17][NH:18][C:27]3[CH:28]=[CH:29][C:30]4[N:31]([CH:33]=[C:34]([C:36]([CH3:42])([CH3:43])[C:37]([O:39][CH2:40][CH3:41])=[O:38])[N:35]=4)[N:32]=3)[CH2:11][CH2:10]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

4

Edukt 3

HCID 11043751Ethyl 6-chloro-α,α-dimethylimidazo[1,2-b]pyridazine-2-acetateHCID 21939870Tetrahydrofuran ethyl acetateHCID 229892803-[4-(Diphenylmethoxy)piperidino]-2-hydroxypropylamine

Produkt 1

HCID 69842735Ethyl 2-[6-[3-[4-(Diphenylmethoxy)piperidino]-2-hydroxypropylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate Difumarate

Versuchsvorschrift

0.511 g of 3-[4-(diphenylmethoxy)piperidino]-2-hydroxypropylamine and 0.268 g of ethyl 2-[6-chloroimidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate were stirred at 190-200° C. for 3 hours. After cooling, ethyl acetate-tetrahydrofuran (2:1) was added; the mixture was washed with aqueous sodium bicarbonate and 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:triethylamine (90:10:1). The desired fraction was collected, dissolved in 5 ml of ethyl acetate; a solution of 82 mg of fumaric acid in 5 ml of methanol was added, followed by concentration. Ethyl ether was added to the residue; the resulting powder was collected by filtration, washed with ethyl ether and dried to yield 0.223 g of the title compound.

Aufarbeitung

  1. temperatureAfter cooling
  2. washthe mixture was washed with aqueous sodium bicarbonate and saturated saline
  3. dry with materialdried with magnesium sulfate
  4. concentrationThe dry product was concentrated under reduced pressure
  5. washeluted with ethyl acetate:methanol:triethylamine (90:10:1)
  6. customThe desired fraction was collected
  7. dissolutiondissolved in 5 ml of ethyl acetate
  8. additiona solution of 82 mg of fumaric acid in 5 ml of methanol was added
  9. concentrationfollowed by concentration
  10. additionEthyl ether was added to the residue
  11. filtrationthe resulting powder was collected by filtration
  12. washwashed with ethyl ether
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8188c6f761d04a45a10c0a0ad446a597
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248740B1

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