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

HRID 2353319Notes

Reaction equation

HRID 2353319 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:32]=[CH:31][C:6]([C:7]([NH:9][C:10]2[CH:30]=[CH:29][C:13]([CH2:14][C:15]3[N:20]4[CH:21]=[CH:22][N:23]=[C:19]4[C:18]([CH2:24][C:25]([O:27]C)=[O:26])=[CH:17][N:16]=3)=[CH:12][CH:11]=2)=[O:8])=[CH:5][CH:4]=1.[OH-].[Na+]>CO>[F:34][C:2]([F:1])([F:33])[C:3]1[CH:32]=[CH:31][C:6]([C:7]([NH:9][C:10]2[CH:30]=[CH:29][C:13]([CH2:14][C:15]3[N:20]4[CH:21]=[CH:22][N:23]=[C:19]4[C:18]([CH2:24][C:25]([OH:27])=[O:26])=[CH:17][N:16]=3)=[CH:12][CH:11]=2)=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57542084Methyl [5-(4-{[4-(trifluoromethyl)benzoyl]amino}benzyl)imidazo[1,2-c]pyrimidin-8-yl]acetate

Product 1

HCID 11539743[5-(4-{[4-(Trifluoromethyl)-benzoyl]amino}benzyl)imidazo[1,2-c]pyrimidin-8-yl]acetic acidYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl [5-(4-{[4-(trifluoromethyl)benzoyl]amino}benzyl)imidazo[1,2-c]-pyrimidin-8-yl]acetate (20 mg, 0.04 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-{[4-(trifluoromethyl)-benzoyl]amino}benzyl)imidazo[1,2-c]pyrimidin-8-yl]acetic acid (14.2 mg, 73%) as slightly brown 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-5beed82eff0441869fa77bbbbe1d0a0c
Source dataset
uspto-grants-2010_07
Patent number
US07750014B2

Reaction notes

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