Potassium Carbonate → 6-[4-Methyl-4-(2-trifluoromethylphenoxy)piperidin-1-YL]pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide

HRID 552167

Reaktionsgleichung

Reaktionsgleichung von HRID 552167
[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12](Cl)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1.[CH3:16][C:17]1([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:20]3[CH2:19][CH2:18][C:17]([CH3:16])([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:31])([F:32])[F:33])[CH2:22][CH2:21]3)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 655615656-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamideHCID 671715074-Methyl-4-(2-trifluoromethylphenoxy)piperidine

Produkt 1

HCID 115396356-[4-Methyl-4-(2-trifluoromethylphenoxy)piperidin-1-YL]pyridazine-3-carboxylic acid (2-cyclopropylethyl)amideAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.020 g, 0.090 mmol) in dioxane (5 mL) was added 4-methyl-4-(2-trifluoromethylphenoxy)piperidine (0.015 g, 0.060 mmol), potassium carbonate (0.033 g, 0.240 mmol) and tetrabutyl ammonium bromide (0.002 g, 0.001 mmol). The resulting mixture was stirred at reflux for 48 hours, filtered and then concentrated in vacuo. The crude product was purified by column chromatography to yield the title compound in 20% yield (0.005 g). 1H NMR (300 MHz, CDCl3) δ 8.02-7.96 (m, 2H), 7.60-7.57 (m, 1H), 7.48-7.40 (m, 1H), 7.14-7.12 (d, J=8.0 Hz, 1H), 7.06-6.99 (m, 2H), 4.25-4.21 (m, 2H), 3.65-3.51 (m, 4H), 2.35-2.31 (m, 2H), 1.85-1.74 (m, 2H), 1.53-1.46 (dd, J=6.6 and 7.0 Hz, 2H), 1.20 (s, 3H), 0.77-0.69 (m, 1H), 0.48-0.42 (m, 2H), 0.11-0.05 (m, 2H). MS (ES+) m/z 449.4 (M+1).

Aufarbeitung

  1. temperatureat reflux for 48 hours
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ecdf6e9ce59441179dbb6b993c0550da
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951805B2

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