Hydrochloric Acid → 1-Methyl-5-(2-phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid

HRID 1958323Notes

Reaction equation

HRID 1958323 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([CH3:31])[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[N:16]=1)=[O:7])C.O.Cl>C1COCC1.C(O)C>[CH3:31][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[N:16]=2)=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=[N:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 673883431-Methyl-5-(2-phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 673918501-Methyl-5-(2-phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

NaOH (3N, 6.9 ml) was added to a solution of 1-methyl-5-(2-phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid ethyl ester (2.70 g, 6.9 mmol) in THF/ethanol=1:1 (40 ml), an the mixture was stirred at RT overnight. Water (10 ml) and HCl (conc., approx. 3 ml) were added to the cooled (0° C.) mixture, until the mixture had a pH of 3. The suspension was stirred for 15 min, and filtered. The precipitate was washed with a small amount of water, and dried under vacuum. The thus obtained product (910 mg, 36%) was used in the next step without further purification. MS (m/e)=361.3 [M−H+].

Workup

  1. temperaturecooled (0° C.) mixture
  2. stirringThe suspension was stirred for 15 min
  3. filtrationfiltered
  4. washThe precipitate was washed with a small amount of water
  5. customdried under vacuum
  6. customThe thus obtained product (910 mg, 36%) was used in the next step without further purification

Sources & evidence

ORD record
ord-20129a3db88f4d8180efb42157c22d70
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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