Hydrochloric Acid → 1-Methyl-4-(2-phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-3-carboxylic acid

HRID 1958334Notes

Reaction equation

HRID 1958334 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]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)=[CH:11][N:10]([CH3:31])[N:9]=1)=[O:7])C.O.Cl>C1COCC1.CO>[CH3:31][N:10]1[CH:11]=[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])=[N:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 673923291-Methyl-4-(2-phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 673917831-Methyl-4-(2-phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-3-carboxylic acidYield 45%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaOH (3N, 1.5 ml) was added to a solution of 1-methyl-4-(2-phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-3-carboxylic acid ethyl ester (390 mg, 1.5 mmol) in a mixture of THF (5 ml) and methanol (5 ml), and the mixture was stirred for 3 h at RT. Water (10 ml) was added, and the mixture was acidified (pH=3) by addition of HCl. The mixture was stirred for 30 min and filtered. The obtained precipitate was washed with a small amount of water, and was dried under vacuum. The thus obtained title compound (240 mg, 45%) was pure enough to be used in the next step. MS (m/e)=363.3 [M+H+].

Workup

  1. stirringThe mixture was stirred for 30 min
  2. filtrationfiltered
  3. washThe obtained precipitate was washed with a small amount of water
  4. customwas dried under vacuum

Sources & evidence

ORD record
ord-c0c38847da11419cb2d6c55328cbbf0d
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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