Water → HCID 67262449, compound

HRID 389134Notes

Reaction equation

HRID 389134 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([OH:28])[CH:6]=[CH:7][C:8]=1[C:9]1[N:13]([CH3:14])[C:12]([C:15]([CH3:27])([O:17][C:18]2[C:23]([F:24])=[CH:22][C:21]([F:25])=[CH:20][C:19]=2[F:26])[CH3:16])=[N:11][N:10]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][C:37]([NH2:39])=[O:38].O>CN(C=O)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[C:9]1[N:13]([CH3:14])[C:12]([C:15]([CH3:16])([O:17][C:18]2[C:23]([F:24])=[CH:22][C:21]([F:25])=[CH:20][C:19]=2[F:26])[CH3:27])=[N:11][N:10]=1)[O:28][CH2:36][C:37]([NH2:39])=[O:38]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 136352702HCID 136352702, compound

Product 1

HCID 67262449HCID 67262449, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3-chloro-4-{4-methyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazol-3-yl}phenol monohydrochloride (40 mg) was suspended in DMF (2 ml), potassium carbonate (64 mg) and 2-bromoacetamide (26 mg) were added thereto, followed by stirring at 60° C. for 30 minutes. The reaction solution was cooled to room temperature, water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine in this order and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:1 to 100:5). The resulting residue was dissolved in ethyl acetate, 4M hydrogen chloride-ethyl acetate (1 ml) was added thereto and the solvent was evaporated under reduced pressure. The residue was washed with ethyl acetate to obtain 2-(3-chloro-4-{4-methyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazol-3-yl}phenoxy}acetamide monohydrochloride (17 mg), as a white solid.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:1 to 100:5)
  7. dissolutionThe resulting residue was dissolved in ethyl acetate
  8. addition4M hydrogen chloride-ethyl acetate (1 ml) was added
  9. customthe solvent was evaporated under reduced pressure
  10. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-e14513b9f5804b739f13555999c9a611
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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