Water → 5-(4-Chlorophenyl)-2-(prop-2-yn-1-yl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714614
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][C@H:15]([OH:20])[C:16]([F:19])([F:18])[F:17])[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.Br[CH2:22][C:23]#[CH:24].C(=O)([O-])[O-].[Cs+].[Cs+].O>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][C@H:15]([OH:20])[C:16]([F:18])([F:19])[F:17])[C:10](=[O:13])[N:11]([CH2:24][C:23]#[CH:22])[N:12]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 595368365-(4-Chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Produkt 1

HCID 866909105-(4-Chlorophenyl)-2-(prop-2-yn-1-yl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1110 mg (3.61 mmol) of the compound from Example 5A were dissolved in 30 ml of acetonitrile, and 451 mg (3.79 mmol) of 3-bromo-1-propyne and 2.35 g (7.22 mmol) of cesium carbonate were added. The mixture was heated under reflux for 1 h. For work-up, the reaction mixture was allowed to cool to RT, and about 30 ml of water were added. The mixture was extracted twice with in each case 30 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1, then 3:1). This gave 203 mg (16% of theory) of the title compound.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 h
  3. extractionThe mixture was extracted twice with in each case 30 ml of ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by chromatography on silica gel (mobile phase

Quellen und Nachweise

ORD-Eintrag
ord-45fad6a5db424d82abd68e26872d8c63
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187466B2

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