Benzyl Chloride → HCID 178434975, compound

HRID 2120860Notes

Reaction equation

HRID 2120860 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[CH:14]=[C:15]([NH2:18])[NH:16][N:17]=1.C(N(CC)CC)C.[CH2:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[O:34]1CCOCC1>O>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[CH:14]=[C:15]([NH:18][C:26](=[O:34])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:16][N:17]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 178434976HCID 178434976, compound

Product 1

HCID 178434975HCID 178434975, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

3-(5-Methyl-3-phenyl-isoxazol-4-yl)-3-oxo-propionitrile (0.391 g, 1.73 mmol) in Ethanol (3 mL) was treated with hydrazine (0.168 mL, 3.46 mmol) and heated to reflux. Evaporation in vacuum gave 5-(5-Methyl-3-phenyl-isoxazol-4-yl)-2H-pyrazol-3-ylamine used without purification. To the resulting amine (0.039 g, 0.16 mmol) in dioxane was added triethyl amine followed by benzyl chloride (0.019 mL, 0.16 mmol). The reaction was stirred at 10° C. for 1 hr and 2 hr at ambient temperature. The solution was diluted with water extracted with ethyl acetate, washed with saturated NaHCO3, Brine, dried over MgSO4 and concentrated in vacuum. HPLC purification afforded 1.4 mg of title compound.

Workup

  1. customused without purification
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated NaHCO3, Brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuum
  6. customHPLC purification

Sources & evidence

ORD record
ord-4248333b348d40e293b82403f7fe07a5
Source dataset
uspto-grants-2004_02
Patent number
US06693108B2

Reaction notes

Loading…