Sodium Hydroxide → (5-{4-[(3,4-Dichlorobenzoyl)amino]benzyl}imidazo[1,2-c]pyrimidin-8-yl)acetic acid

HRID 2353326Notes

Reaction equation

HRID 2353326 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[Cl:32])[C:5]([NH:7][C:8]1[CH:28]=[CH:27][C:11]([CH2:12][C:13]2[N:18]3[CH:19]=[CH:20][N:21]=[C:17]3[C:16]([CH2:22][C:23]([O:25]C)=[O:24])=[CH:15][N:14]=2)=[CH:10][CH:9]=1)=[O:6].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[Cl:32])[C:5]([NH:7][C:8]1[CH:28]=[CH:27][C:11]([CH2:12][C:13]2[N:18]3[CH:19]=[CH:20][N:21]=[C:17]3[C:16]([CH2:22][C:23]([OH:25])=[O:24])=[CH:15][N:14]=2)=[CH:10][CH:9]=1)=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57542077Methyl (5-{4-[(3,4-dichloro-benzoyl)amino]benzyl}imidazo[1,2-c]pyrimidin-8-yl)acetate

Product 1

HCID 11568722(5-{4-[(3,4-Dichlorobenzoyl)amino]benzyl}imidazo[1,2-c]pyrimidin-8-yl)acetic acidYield 75.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl (5-{4-[(3,4-dichlorobenzoyl)amino]benzyl}imidazo[1,2-c]pyrimidin-8-yl)-acetate (25 mg, 0.05 mmol) in methanol (1 mL) was added 1M NaOH aqueous solution (0.2 mL) at room temperature, and the mixture was stirred for 1 hour. After the removal of methanol under reduced pressure, water was added to the residue. The solution was washed with diethyl ether and neutralized by aqueous hydrochloric acid. The resulting precipitates were collected by filtration and dried under reduced pressure to give (5-{4-[(3,4-dichlorobenzoyl)amino]benzyl}imidazo[1,2-c]pyrimidin-8-yl)acetic acid (17.2 mg, 71%) as slightly yellow solid.

Workup

  1. customAfter the removal of methanol under reduced pressure, water
  2. additionwas added to the residue
  3. washThe solution was washed with diethyl ether
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-cd78c5a6e18146f78442449df114b27e
Source dataset
uspto-grants-2010_07
Patent number
US07750014B2

Reaction notes

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