Potassium Carbonate → HCID 131730771, Verbindung

HRID 80895

Reaktionsgleichung

Reaktionsgleichung von HRID 80895
[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.Cl.Cl.[NH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[ClH:1].[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([C:5]2[N:4]=[N:3][C:2]([N:23]3[CH2:24][CH2:25][CH2:26][CH:21]([NH2:20])[CH2:22]3)=[CH:7][CH:6]=2)=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 12449554Pyridazine, 3-chloro-6-[4-(trifluoromethyl)phenyl]-HCID 16211870Piperidin-3-amine dihydrochloride

Produkt 1

HCID 131730771HCID 131730771, VerbindungAusbeute 27,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

3-Chloro-6-(4-trifluoromethylphenyl)pyridazine (0.2 g, 0.77 mmol), 3-aminopiperidine dihydrochloride (0.27 g, 1.54 mmol) and potassium carbonate (0.53 g, 3.87 mmol) were mixed in acetone (4 mL) in a 20 mL microwave vessel. The reaction mixture was heated in a microwave oven for 2 h at 120° C. The reaction mixture was filtered and the precipitate was washed with MeOH. The combined organic phases were evaporated. The crude oil was purified on a silicagel column (0.04-0.063 mesh) using dichloromethane/MeOH (9:1) as eluent. This afforded 110 mg of a oil that was dissolved in MeOH and acidified with concentrated HCl (5 mL). The mixture was evaporated and the residue was dissolved in MeOH (1 mL) and ether (100 mL) was added with stirring. The mixture was evaporated to give 76 mg (25%) of the title compound as a yellow solid.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washthe precipitate was washed with MeOH
  3. customThe combined organic phases were evaporated
  4. customThe crude oil was purified on a silicagel column (0.04-0.063 mesh)
  5. dissolutionThis afforded 110 mg of a oil that was dissolved in MeOH
  6. customThe mixture was evaporated
  7. dissolutionthe residue was dissolved in MeOH (1 mL)
  8. additionether (100 mL) was added
  9. customThe mixture was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-fee32dfc11fb4f769ef6a6273104e86b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846677B2

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