Trifluoroacetic acid → 1-{4-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-5-methylimidazolidin-2-one

HRID 2411777Notes

Reaction equation

HRID 2411777 reaction equation
[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]([CH3:28])[CH2:26][N:25](CC5C=CC(OC)=CC=5)[C:24]4=[O:38])=[CH:19][CH:18]=3)=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[C:3]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([N:23]4[CH:27]([CH3:28])[CH2:26][NH:25][C:24]4=[O:38])=[CH:21][CH:22]=3)=[O:16])[CH2:13][CH2:14]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 712522003-{4-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-1-(4-methoxybenzyl)-4-methylimidazolidin-2-one

Product 1

HCID 712528351-{4-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-5-methylimidazolidin-2-oneYield 106.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-1-(4-methoxybenzyl)-4-methylimidazolidin-2-one (105 mg) described in Example 420 was dissolved in dichloromethane (1 mL), trifluoroacetic acid (2 mL) was added, and the mixture was stirred at room temperature overnight. The solvent was evaporated from the reaction mixture, 5% aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with chloroform/methanol (10/1). The organic layer was dried over sodium sulfate, and the solvent was evaporated. The obtained residue was suspension washing with IPE to give the title compound (86 mg).

Workup

  1. customThe solvent was evaporated from the reaction mixture, 5% aqueous sodium hydrogen carbonate solution
  2. additionwas added
  3. extractionthe mixture was extracted with chloroform/methanol (10/1)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated
  6. washwashing with IPE

Sources & evidence

ORD record
ord-e8a930c054cd48afa19bcd633beb4d82
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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