Sodium Bicarbonate → Ethyl 2-[3-chloro-6-[3-[4-(diphenylmethoxy)piperidino]propylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate dihydrochloride

HRID 1169072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1169072
[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][NH2:18])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:25][C:26]1[N:30]2[N:31]=[C:32](Cl)[CH:33]=[CH:34][C:29]2=[N:28][C:27]=1[C:36]([CH3:43])([CH3:42])[C:37]([O:39][CH2:40][CH3:41])=[O:38].C(=O)(O)[O-].[Na+]>>[ClH:25].[ClH:25].[Cl:25][C:26]1[N:30]2[N:31]=[C:32]([NH:18][CH2:17][CH2:16][CH2:15][N:12]3[CH2:13][CH2:14][CH:9]([O:8][CH:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:10][CH2:11]3)[CH:33]=[CH:34][C:29]2=[N:28][C:27]=1[C:36]([CH3:42])([CH3:43])[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Komponenten

4

Edukt 3

HCID 516892Sodium BicarbonateHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamineHCID 22989216Ethyl 2-(3,6-dichloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropionate

Produkt 1

HCID 22989228Ethyl 2-[3-chloro-6-[3-[4-(diphenylmethoxy)piperidino]propylamino]imidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate dihydrochlorideAusbeute 152,8 %

Versuchsvorschrift

2.56 g of 4-(diphenylmethoxy)-1-piperidinepropanamine and 1.19 g of ethyl 2-[3,6-dichloroimidazo[1,2-b]pyridazin-2-yl]-2-methylpropionate were stirred at 160° for 3 hours. After cooling, aqueous sodium bicarbonate was added, followed by extraction with ethyl acetate; the extract was washed with saturated saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol:triethylamine (50:5:1). The desired fraction was collected and dissolved in 5 ml of ethyl acetate; 0.80 ml of a 4 N hydrogen chloride solution in ethyl acetate was added, followed by concentration. The residue was powdered by the addition of ether and dried to yield 1.33 g of the title compound.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract was washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with ethyl acetate:methanol:triethylamine (50:5:1)
  7. customThe desired fraction was collected
  8. dissolutiondissolved in 5 ml of ethyl acetate
  9. addition0.80 ml of a 4 N hydrogen chloride solution in ethyl acetate was added
  10. concentrationfollowed by concentration
  11. additionThe residue was powdered by the addition of ether
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8aadff28a6f04ea789a9573372874aa9
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06627630B1

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