Diisopropylethylamine → 7-Fluoro-2-(3-hydroxyazetidin-1-yl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17418

Reaktionsgleichung

Reaktionsgleichung von HRID 17418
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[F:11])[N:6]=1.C(N(C(C)C)CC)(C)C.[CH2:30]1[NH:33][CH2:32][CH:31]1[OH:34].Cl>C(Cl)Cl>[F:11][C:10]1[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]([CH3:18])[C:7]([C:19]#[N:20])=[C:5]2[C:4]=1[O:3][C:2]([N:33]1[CH2:30][CH:31]([OH:34])[CH2:32]1)=[N:6]2

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 685853627-Fluoro-2-(3-hydroxyazetidin-1-yl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (100 mg, 0.35 mmol) was dissolved in methylene chloride (2 ml), then diisopropylethylamine (237 μl, 1.39 mmol) and 3-hydroxy-1-azetidine hydrochloride (76 mg, 0.70 mmol) were added, followed by heating under reflux in a sealed tube under nitrogen atmosphere for 6 hours. After cooling, dilution with methylene chloride and washing with water and saturated brine, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resisting residue was recrystallized and purified with n-hexane/ethyl acetate to obtain the entitled compound (123 mg, quant) as a yellow white solid.

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux in a sealed tube under nitrogen atmosphere for 6 hours
  3. temperatureAfter cooling
  4. washdilution with methylene chloride and washing with water and saturated brine
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customThe resisting residue was recrystallized
  8. custompurified with n-hexane/ethyl acetate
  9. customto obtain the entitled compound (123 mg, quant) as a yellow white solid

Quellen und Nachweise

ORD-Eintrag
ord-644a1969a68a477b87021288bfd2da9a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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