Sodium Hydroxide → 4-[5-(2-chlorophenyl)-4-(4-{[2-(trimethylsilyl)-ethoxy]methyl}-4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-amine

HRID 537057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 537057
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([C:13]2[C:18]([CH3:19])=[CH:17][N:16]=[C:15]([NH:20]C(=O)C)[CH:14]=2)=[N:10][C:9]=1[C:24]1[N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH:27]=[N:26][N:25]=1.[OH-].[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([C:13]2[C:18]([CH3:19])=[CH:17][N:16]=[C:15]([NH2:20])[CH:14]=2)=[N:10][C:9]=1[C:24]1[N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:34])([CH3:36])[CH3:35])[CH:27]=[N:26][N:25]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 66749586N-{4-[5-(2-chlorophenyl)-4-(4-{[2-(trimethylsilyl)ethoxy]methyl}-4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide

Produkt 1

HCID 667495874-[5-(2-chlorophenyl)-4-(4-{[2-(trimethylsilyl)-ethoxy]methyl}-4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-amineAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of N-{4-[5-(2-chlorophenyl)-4-(4-{[2-(trimethylsilyl)ethoxy]methyl}-4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (0.42 g, 0.80 mmol), EtOH (25 mL) and aqueous NaOH (1M, 3 mL) was allowed to stir at reflux for 5 h. The reaction mixture was concentrated and the residue was washed with hexane. Diethyl ether was added and the mixture was filtered. The filtrate was concentrated to give 4-[5-(2-chlorophenyl)-4-(4-{[2-(trimethylsilyl)-ethoxy]methyl}-4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-amine (0.24 g, 62%) which was used in the next step without purification. LCMS (AA): m/z=483 (M+H).

Aufarbeitung

  1. temperatureat reflux for 5 h
  2. concentrationThe reaction mixture was concentrated
  3. washthe residue was washed with hexane
  4. additionDiethyl ether was added
  5. filtrationthe mixture was filtered
  6. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-77fa98794c1f41dcbf7b4b37843cfc6e
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859768B2

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