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 537057Notes

Reaction equation

HRID 537057 reaction equation
[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

Participants

4

Reactant 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

Product 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-amineYield 62.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-77fa98794c1f41dcbf7b4b37843cfc6e
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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