Sodium Hydroxide → sodium 2-(5-amino-3-phenyl-4-(phenylethynyl)-1H-pyrazol-1-yl)acetate

HRID 1615730Notes

Reaction equation

HRID 1615730 reaction equation
C([NH:4][C:5]1[N:9]([CH2:10][C:11]([O:13]CC)=[O:12])[N:8]=[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]=1[C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=O)C.[OH-].[Na+:31]>C(O)C>[NH2:4][C:5]1[N:9]([CH2:10][C:11]([O-:13])=[O:12])[N:8]=[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]=1[C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Na+:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70983078ethyl 2-(5-acetamido-3-phenyl-4-(phenylethynyl)-1H-pyrazol-1-yl)acetate

Product 1

HCID 70982572sodium 2-(5-amino-3-phenyl-4-(phenylethynyl)-1H-pyrazol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 2-[5-acetamido-3-phenyl-4-(2-phenylethynyl)pyrazol-1-yl]acetate (13 g, 34 mmol), ethanol (150 mL) and 25% aq. NaOH solution (150 mL) was stirred and heated to 80° C. for 8 h and cooled to room temperature. Upon cooling, a precipitate formed. The precipitate was filtered and washed with cooled mixture of ethyl acetate/water (1:1). The solid was further triturated with diethyl ether, filtered and dried to provide 9.8 g of the title compound.

Workup

  1. temperaturecooled to room temperature
  2. temperatureUpon cooling
  3. customa precipitate formed
  4. filtrationThe precipitate was filtered
  5. washwashed
  6. temperaturewith cooled
  7. additionmixture of ethyl acetate/water (1:1)
  8. customThe solid was further triturated with diethyl ether
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-50da356e6a79408091d15014a6e7b89d
Source dataset
uspto-grants-2014_07
Patent number
US08765762B2

Reaction notes

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