4-(1-Pyrrolidinyl)piperidine → 2-Phenyl-3-pyrid-4-yl-6-(4-pyrrolidin-1-ylpiperid-1-yl)imidazo[1,2-b]pyridazine

HRID 1803903

Reaktionsgleichung

Reaktionsgleichung von HRID 1803903
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[N:7]=1.[N:23]1([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH2:27][CH2:26][CH2:25][CH2:24]1>C(O)C>[C:11]1([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([N:31]4[CH2:32][CH2:33][CH:28]([N:23]5[CH2:27][CH2:26][CH2:25][CH2:24]5)[CH2:29][CH2:30]4)=[N:7][N:6]3[C:8]=2[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

4

Edukt 2

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 594069546-Chloro-2-phenyl-3-pyrid-4-ylimidazo[1,2-b]pyridazine

Produkt 1

HCID 594069552-Phenyl-3-pyrid-4-yl-6-(4-pyrrolidin-1-ylpiperid-1-yl)imidazo[1,2-b]pyridazineAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
155 °C

Versuchsvorschrift

A mixture of 4.03 g (13.1 mmol) of 6-chloro-2-phenyl-3-pyrid-4-ylimidazo[1,2-b]pyridazine and 4.4 g (29 mmol) of 4-pyrrolidin-1-ylpiperidine in 50 mL of ethanol is heated at 155° C. for 4 hours. After cooling, the solvent is evaporated off under reduced pressure and the residue is chromatographed on silica gel, eluting with a mixture of dichloromethane and methanol (93:7). The product is then recrystallized from 40 mL of methanol to give 1.5 g of yellow crystals after drying under reduced pressure.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe solvent is evaporated off under reduced pressure
  3. customthe residue is chromatographed on silica gel
  4. washeluting with a mixture of dichloromethane and methanol (93:7)
  5. customThe product is then recrystallized from 40 mL of methanol

Quellen und Nachweise

ORD-Eintrag
ord-d74563b07826453e8a6b0f5a747daba8
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354405B2

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