1H-1,2,4-Triazole → HCID 22859137, compound

HRID 2397012Notes

Reaction equation

HRID 2397012 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].[H][H].[N:10]1([CH2:15][C@@:16]([C:25]2[CH:30]=[CH:29][C:28](F)=[CH:27][C:26]=2[F:32])([OH:24])[C@H:17]([N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)[CH3:18])[CH:14]=[N:13][CH:12]=[N:11]1>CN(C)C=O>[N:10]1([CH2:15][C@@:16]([C:25]2[CH:30]=[CH:29][C:28]([N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)=[CH:27][C:26]=2[F:32])([OH:24])[C@H:17]([N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)[CH3:18])[CH:14]=[N:13][CH:12]=[N:11]1

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 53712382HCID 53712382, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22859137HCID 22859137, compoundYield 5,734.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1H-1,2,4-Triazole (0.3 mg) was added portionwise to a stirred dispersion of 60% sodium hydride in oil (0.16 g) in dimethylformamide (15 ml) under ice-cooling in a stream of nitrogen, followed by further stirring for 15 minutes. When the evolution of hydrogen (ceased), (2R,3R)-1,3-bis (1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-2-butanol (0.64 g) was added to the mixture. The mixture was stirred for 3 hours at 150° C. After cooling, the reaction mixture was added into ice-water and extracted with ethyl acetate. The extract was washed with water and saturated saline and dried. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (silica gel 30 g, eluent: ethyl acetate/acetone/methanol=5:4:1) to give the title compound (Compound 11, 92 mg) as colorless needles.

Workup

  1. temperaturecooling in a stream of nitrogen
  2. stirringThe mixture was stirred for 3 hours at 150° C
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and saturated saline
  6. customdried
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (silica gel 30 g, eluent: ethyl acetate/acetone/methanol=5:4:1)

Sources & evidence

ORD record
ord-8c02918aa4ee4fb3a16859e7ea052877
Source dataset
uspto-grants-1996_02
Patent number
US05495024

Reaction notes

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