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Hydrochloric Acid → 5-(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid

HRID 2382741
Notes
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Reaction equation

HRID 2382741 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([CH3:32])[C:12]=1[C:13](=[O:31])[NH:14][C:15]1[C:20]([Br:21])=[CH:19][N:18]2[CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=[C:17]2[CH:16]=1)=[O:7])C.O.Cl>C1COCC1.CO>[Br:21][C:20]1[C:15]([NH:14][C:13]([C:12]2[N:11]([CH3:32])[N:10]=[CH:9][C:8]=2[C:6]([OH:7])=[O:5])=[O:31])=[CH:16][C:17]2[N:18]([CH:22]=[C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:24]=2)[CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 670422785-(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 670416185-(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents

2
HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaOH (3N, 0.65 ml) was added to a solution of 5-(6-bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (460 mg, 0.98 mmol) in a mixture of THF (5 ml) and methanol (5 ml), and the reaction mixture was stirred at r.t. overnight. An additional amount of NaOH (3N, 0.65 ml) and water (2 ml) were added and the mixture was heated to reflux (1 h). After cooling to r.t., HCl (conc., ˜0.7 ml) was added to the cooled mixture, and the brown suspension was stirred at r.t. (15 min). The suspension was then filtered, and the precipitated title compound (150 mg, 35%) was washed with a small amount of water, dried under vacuum, and used in the next step without further purification. MS (m/e)=440.3 [M+H+].

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux (1 h)
  3. temperatureAfter cooling to r.t.
  4. stirringthe brown suspension was stirred at r.t. (15 min)
  5. filtrationThe suspension was then filtered
  6. customthe precipitated title compound (150 mg, 35%)
  7. washwas washed with a small amount of water
  8. customdried under vacuum
  9. customused in the next step without further purification

Sources & evidence

ORD record
ord-85dc7ca6634a4c189b8efd506f6fe397
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08263584B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes