4-Ethoxyaniline → HCID 178466725, compound

HRID 2220136Notes

Reaction equation

HRID 2220136 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[C:5]([C:11]#[N:12])=[C:4]([OH:13])[C:3]=1[CH3:14].[CH3:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=1>CC(O)C.C(OCC)(=O)C>[CH2:16]([O:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:2]2[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[C:5]([C:11]#[N:12])=[C:4]([OH:13])[C:3]=2[CH3:14])=[CH:22][CH:23]=1)[CH3:15]

Participants

5

Reactant 2

HCID 90764-EthoxyanilineHCID 178431609HCID 178431609, compound

Product 1

HCID 178466725HCID 178466725, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude product (9.25 mg) of 7-chloro-5-hydroxy-6-methylpyrazolo[1,5-a]pyridine-4-carbonitrile (13) was dissolved in 2-propanol (2.2 mL). To this solution, p-phenetidine (289 μL) was added and the mixture was stirred under reflux with heating for 3 days. After cooled to room temperature, the reaction solution was diluted with ethyl acetate. This solution was washed with a mixture of brine and 1 mol/L hydrochloric acid (1:1) and then with a mixture of brine and saturated aqueous sodium hydrogen carbonate solution (9:1) and dried over sodium sulfate. After the solvent was removed under reduced pressure, the residue was purified with silica-gel column chromatography (hexane/ethyl acetate=1/1) to obtain the title compound (21) (77.8 mg, Yield 56%).

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 3 days
  3. washThis solution was washed with a mixture of brine and 1 mol/L hydrochloric acid (1:1)
  4. additionwith a mixture of brine and saturated aqueous sodium hydrogen carbonate solution (9:1)
  5. dry with materialdried over sodium sulfate
  6. customAfter the solvent was removed under reduced pressure
  7. customthe residue was purified with silica-gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-44afef575bc84a53a9bb71ea207d1a7b
Source dataset
uspto-grants-2008_08
Patent number
US07417053B2

Reaction notes

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