Potassium Carbonate → 1-[1-(4-Chlorophenyl)-5-isopropylpyrazol-4-yl]-3-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]pyrrolidin-2-one

HRID 522332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 522332
Br[CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[N:9][N:10]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[C:11]=2[CH:12]([CH3:14])[CH3:13])[C:3]1=[O:22].[CH3:23][C:24]1[NH:25][CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:28]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([N:10]2[C:11]([CH:12]([CH3:14])[CH3:13])=[C:7]([N:4]3[CH2:5][CH2:6][CH:2]([N:25]4[CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:28]=[C:24]4[CH3:23])[C:3]3=[O:22])[CH:8]=[N:9]2)=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 867230453-Bromo-1-[1-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-oneHCID 178432834HCID 178432834, Verbindung

Produkt 1

HCID 762829761-[1-(4-Chlorophenyl)-5-isopropylpyrazol-4-yl]-3-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]pyrrolidin-2-oneAusbeute 26,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 3-bromo-1-[1-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one (0.110 g, 0.29 mmol), 2-methyl-4-(trifluoromethyl)-1H-imidazole (0.080 g, 0.53 mmol) and K2CO3 (0.080 g, 0.58 mmol) in DMF (1.8 mL) was stirred at 65° C. for 2 hrs. The mixture was then cooled to room temperature, quenched with water (30 mL), extracted with EtOAc (50 mL), and purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to yield the title compound (0.035 g, TFA salt, 21%). 1H NMR (TFA salt) (400 MHz, CDCl3) δ 7.58 (s, 1H), 7.49 (m, 2H), 7.35 (m, 2H), 7.27 (s, 1H), 5.03 (dd, J=10.4, 8.8 Hz, 1H), 3.89 (m, 1H), 3.81 (m, 1H), 3.04 (heptet, J=6.8 Hz, 1H), 2.88 (m, 1H), 2.58 (s, 3H), 2.40 (m, 1H), 1.23 (m, 6H); MS: (ES) m/z calculated for C21H21ClF3N5O [M+H]+452.1. found 452.1.

Aufarbeitung

  1. temperatureThe mixture was then cooled to room temperature
  2. customquenched with water (30 mL)
  3. extractionextracted with EtOAc (50 mL)
  4. custompurified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-97e2ace9eb1b4a389bcc915d654d40ce
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328116B2

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