Potassium Hydroxide → HCID 67041914, compound

HRID 2382733Notes

Reaction equation

HRID 2382733 reaction equation
[OH-].[K+].C([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([CH2:31][CH3:32])[C:12]=1[C:13](=[O:30])[NH:14][C:15]1[CH:20]=[CH:19][N:18]2[CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:23]=[C:17]2[CH:16]=1)=[O:7])C>C(O)C>[CH2:31]([N:11]1[C:12]([C:13](=[O:30])[NH:14][C:15]2[CH:20]=[CH:19][N:18]3[CH:21]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:23]=[C:17]3[CH:16]=2)=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=[N:10]1)[CH3:32]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 51034366HCID 51034366, compound

Product 1

HCID 67041914HCID 67041914, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

KOH (70 mg) was added to a solution of 1-ethyl-5-(2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester (Example 12, 215 mg, 0.53 mmol) in ethanol (6 ml), and the mixture was heated to reflux until HPLC control indicated the consumption of the starting material (2 h). Upon cooling, HCl (conc.) was added dropwise, until the pH reached ˜2 (few drops). The suspension was stirred at r.t. (30 min.) and then filtered. The precipitate was washed with little ethanol and dried under vacuum. The thus obtained title compound (160 mg, 80%) was used in the next step without further purification. MS (m/e)=376.4 [M+H+].

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux until HPLC control
  3. customthe consumption of the starting material (2 h)
  4. temperatureUpon cooling
  5. additionHCl (conc.) was added dropwise, until the pH
  6. filtrationfiltered
  7. washThe precipitate was washed with little ethanol
  8. customdried under vacuum

Sources & evidence

ORD record
ord-687cc8208cce488bab4f1d05bda4c322
Source dataset
uspto-grants-2012_09
Patent number
US08263584B2

Reaction notes

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