Sodium Hydroxide → HCID 86717293, compound

HRID 588593Notes

Reaction equation

HRID 588593 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:17]=[N:18][CH:19]=[CH:20][CH:21]=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+]>C(O)C>[NH2:4][C:5]1[N:9]([CH2:10][C:11]([OH:13])=[O:12])[N:8]=[C:7]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[C:6]=1[C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86717294HCID 86717294, compound

Product 1

HCID 86717293HCID 86717293, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of ethyl 2-[5-acetamido-4-(2-phenylethynyl)-3-(3-pyridyl)pyrazol-1-yl]acetate (410 mg, 1.1 mmol) in ethanol (10 mL) was added 25% NaOH aqueous solution (6.5 mL). The reaction mixture was stirred at 85° C. for 6 h. The reaction mixture was cooled down to room temperature and ethanol was evaporated in vacuo. The resulting aqueous suspension was filtered and the solid was washed with acetonitrile and dried, yielding 235 mg of 2-[5-amino-4-(2-phenylethynyl)-3-(3-pyridyl)pyrazol-1-yl]acetic acid.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. customethanol was evaporated in vacuo
  3. filtrationThe resulting aqueous suspension was filtered
  4. washthe solid was washed with acetonitrile
  5. customdried

Sources & evidence

ORD record
ord-9685bbcd37084ad9845b34ab6484571c
Source dataset
uspto-grants-2016_01
Patent number
US09227976B2

Reaction notes

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