Hydrazine → HCID 178434976, compound

HRID 1375636Notes

Reaction equation

HRID 1375636 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](=O)[CH2:14][C:15]#[N:16].[NH2:18][NH2:19]>C(O)C>[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]([NH2:16])[NH:18][N:19]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 234356403-(5-Methyl-3-phenyl-isoxazol-4-yl)-3-oxo-propionitrile

Product 1

HCID 178434976HCID 178434976, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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. temperatureheated to reflux
  2. customEvaporation in vacuum

Sources & evidence

ORD record
ord-fefe7a6a70d4482696482a0a4032e18a
Source dataset
uspto-grants-2007_01
Patent number
US07169798B2

Reaction notes

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