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

HRID 751586Notes

Reaction equation

HRID 751586 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 Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-benzoic acid ethyl ester (30 mmol), 1N aqueous sodium hydroxide (50 mL), and ethanol (80 mL) is heated at reflux for 1.5 hr. The mixture is cooled and the ethanol removed in vacuo. The residue is diluted with iN sodium hydroxide (30 mL) and washed with ethyl acetate (2×100 mL). The aqueous layer is brought to pH 6 with 3N HCl, and the mixture filtered to give 4-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-benzoic acid (7) as a light orange solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1.5 hr
  3. temperatureThe mixture is cooled
  4. customthe ethanol removed in vacuo
  5. additionThe residue is diluted with iN sodium hydroxide (30 mL)
  6. washwashed with ethyl acetate (2×100 mL)
  7. filtrationthe mixture filtered

Sources & evidence

ORD record
ord-aafcf933638d441885cef703caded5f7
Source dataset
uspto-grants-2008_07
Patent number
US07405295B2

Reaction notes

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