Sodium Hydroxide → 4-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-benzoic Acid

HRID 551876Notes

Reaction equation

HRID 551876 reaction equation
C([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]3[N:14]([CH:19]=[CH:20][N:21]=3)[CH:15]=[C:16]([Br:18])[N:17]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+]>C(O)C>[Br:18][C:16]1[N:17]=[C:12]([NH:11][C:8]2[CH:7]=[CH:6][C:5]([C:4]([OH:22])=[O:3])=[CH:10][CH:9]=2)[C:13]2[N:14]([CH:19]=[CH:20][N:21]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 597547334-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-benzoic acid ethyl ester

Product 1

HCID 597546904-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-benzoic AcidYield 86.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-benzoic acid ethyl ester (10.0 g; 27.7 mmol) is dissolved in 200 mL ethanol (200 proof) and 100 mL 1 N NaOH is added. The reaction is refluxed for 2 hours and then cooled to rt. The resulting solid is filtered and collected, then slurried up in 0.1 N HCl (75 mL) and extracted with CH2Cl2 (2×75 mL). The pooled CH2Cl2 layers is washed with brine, then dried over anhydrous sodium sulfate and concentrated in vacuo to provide 4-(6-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-benzoic acid as a white solid (8 g).

Workup

  1. temperatureThe reaction is refluxed for 2 hours
  2. filtrationThe resulting solid is filtered
  3. customcollected
  4. extractionextracted with CH2Cl2 (2×75 mL)
  5. washThe pooled CH2Cl2 layers is washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e28e02d421b04cb7bf7e97ce092c7db0
Source dataset
uspto-grants-2011_05
Patent number
US07947835B2

Reaction notes

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