Citric Acid → HCID 57526883, compound

HRID 1452522Notes

Reaction equation

HRID 1452522 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][CH:29]=[CH:28][C:4]=1[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13](S(C)=O)[N:12]=2)[N:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:7]1=[O:27])#[N:2].[H-].[Na+].C(O)(=O)[CH2:35][C:36](CC(O)=O)([C:38](O)=O)[OH:37]>C(O)(C)C>[C:1]([C:3]1[CH:31]=[CH:30][CH:29]=[CH:28][C:4]=1[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([O:37][CH:36]([CH3:38])[CH3:35])[N:12]=2)[N:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:7]1=[O:27])#[N:2]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 23020390HCID 23020390, compound

Product 1

HCID 57526883HCID 57526883, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In 5 ml of isopropanol was suspended 100 mg of 1-(2-cyano-benzyl)-3-(4-fluorophenyl)-4-(2-methylsulfinylpyrimidin-4-yl)-4-imidazolin-2-one (Compound of Reference example 6(2) or Reference example 7(2)), 26.3 mg of sodium hydride was added to the mixture and the resulting mixture was stirred at room temperature for 5 hours. To the reaction mixture were successively added an aqueous citric acid solution and an aqueous sodium bicarbonate solution, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed, dried and concentrated, and the residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to give 68 mg of the title compound as powder.

Workup

  1. additionwas added to the mixture
  2. extractionan aqueous sodium bicarbonate solution, and the resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-4eee954f2ca04bc3b5d59d31f74db402
Source dataset
uspto-grants-2009_01
Patent number
US07473695B2

Reaction notes

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