Dimethylamine → HCID 57743004, Verbindung

HRID 1896386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896386
Cl[C:2]1[S:3][C:4]([CH2:7][N:8]2[CH2:12][CH:11]([C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=3[F:21])[CH2:10][C:9]2=[O:22])=[CH:5][N:6]=1.[CH3:23][NH:24][CH3:25].O[Li].O>C1COCC1.O>[CH3:23][N:24]([CH3:25])[C:2]1[S:3][C:4]([CH2:7][N:8]2[CH2:12][CH:11]([C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=3[F:21])[CH2:10][C:9]2=[O:22])=[CH:5][N:6]=1

Komponenten

6

Edukt 3

HCID 674Dimethylamine2×HCID 168937Lithium hydroxide, monohydrateHCID 57742995HCID 57742995, Verbindung

Produkt 1

HCID 57743004HCID 57743004, VerbindungAusbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a sealed tube fitted with a magnetic stirrer, 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-(2,3,5-trifluorophenyl)pyrrolidin-2-one 250 (0.3 g, 0.87 mmol) is dissolved in a mixture of THF (4 ml) and H2O (0.1 ml). Dimethylamine (0.85 ml, 1.7 mmol) and LiOH.H2O (0.043 g, 1 mmol) are added and the mixture is stirred at room temperature for 12 h and heated at 50° C. overnight. Dimethylamine (3×3.4 mmol, then 1×5.1 mmol) is added after 24 h, 48 h, 72 h and 96 h heating. THF is evaporated, the residue is dissolved in water and CH2Cl2, the pH of the aqueous phase is brought to 9 and the aqueous phase is extrated with CH2Cl2. The combined organic phases are dried over MgSO4, filtered and concentrated. The crude product is purified by chromatography on silicagel and recrystallized from diisopropylether to afford 0.1 g of 1-{[2-(dimethylamino)-1,3-thiazol-5-yl]methyl}-4-(2,3,5-trifluorophenyl)pyrrolidin-2-one 251.

Aufarbeitung

  1. customIn a sealed tube fitted with a magnetic stirrer
  2. temperatureheated at 50° C. overnight
  3. temperatureheating
  4. customTHF is evaporated
  5. dissolutionthe residue is dissolved in water
  6. dry with materialThe combined organic phases are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified by chromatography on silicagel
  10. customrecrystallized from diisopropylether

Quellen und Nachweise

ORD-Eintrag
ord-1e1e548f427948cab6b10c06db9344c6
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518943B2

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