p-Toluenesulfonic acid → 4-(1H-Imidazol-1-yl)-2-(6-piperidin-1-ylpyrimidin-4-yl)-1,2-dihydro-3H-pyrazol-3-one

HRID 1753824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1753824
C(O[C:4](=[O:15])[C:5]([N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)=[CH:6][N:7](C)C)C.[NH:16]([C:18]1[CH:23]=[C:22]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[N:21]=[CH:20][N:19]=1)N.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)(=O)C>[N:10]1([C:5]2[C:4](=[O:15])[N:16]([C:18]3[CH:23]=[C:22]([N:24]4[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]4)[N:21]=[CH:20][N:19]=3)[NH:7][CH:6]=2)[CH:14]=[CH:13][N:12]=[CH:11]1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 441403054-Hydrazinyl-6-(piperidin-1-yl)pyrimidineHCID 66726242Ethyl 3-(N,N-dimethylamino)-2-(1H-imidazol-1-yl)acrylate

Produkt 1

HCID 596036554-(1H-Imidazol-1-yl)-2-(6-piperidin-1-ylpyrimidin-4-yl)-1,2-dihydro-3H-pyrazol-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5.5 g (26.3 mmol) of the compound from Example 42A and 6.1 g (31.5 mmol) of the compound from Example 8A are dissolved in 55 ml ethyl acetate and 1.2 g (10.5 mmol) p-toluenesulfonic acid are added. The mixture is heated to the reflux and is stirred at this temperature for 16 h. After cooling to RT, the precipitate is filtered off and washed with ethyl acetate. The solid is dissolved in 50 ml water and the solution is adjusted to pH 7 with 1 N hydrochloric acid. The precipitate is filtered off, washed with water and diisopropyl ether and finally dried over phosphorus pentoxide.

Aufarbeitung

  1. temperatureThe mixture is heated to the
  2. temperaturereflux
  3. filtrationthe precipitate is filtered off
  4. washwashed with ethyl acetate
  5. dissolutionThe solid is dissolved in 50 ml water
  6. filtrationThe precipitate is filtered off
  7. washwashed with water and diisopropyl ether
  8. dry with materialfinally dried over phosphorus pentoxide

Quellen und Nachweise

ORD-Eintrag
ord-ff1426cd92e84ca8883edc7c09cecee7
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09168249B2

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