Trifluoroacetic acid → HCID 22337014, compound

HRID 585514Notes

Reaction equation

HRID 585514 reaction equation
C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.[NH2:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH:18](O)[N:19]([CH2:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34]#[N:35])[CH:30]=[CH:31][CH:32]=1)[C:20]2=[O:25]>ClCCl>[NH2:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH2:18][N:19]([CH2:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34]#[N:35])[CH:30]=[CH:31][CH:32]=1)[C:20]2=[O:25]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 22337029HCID 22337029, compound

Product 1

HCID 22337014HCID 22337014, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, initially 8 ml (50 mmol) of triethylsilane and then dropwise, 20 ml (260 mmol) of TFA are added to a suspension of 5.87 g (20 mmol, purity about 90%) of 2-{3-[(4-amino-3-hydroxy-1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetonitrile in 200 ml dichloromethane. The mixture is stirred at room temperature for 4 h and then concentrated and dried under high vacuum. The residue is taken up in dichloromethane and the mixture is washed with sat. sodium bicarbonate solution and sat. sodium chloride solution, dried over magnesium sulfate and concentrated to about 50 ml. About 100 ml of ether are added to the crystal slurry, which is then stirred for about 2 h and filtered. Yield: 4.36 g (78.7% of theory);

Workup

  1. concentrationconcentrated
  2. customdried under high vacuum
  3. washthe mixture is washed with sat. sodium bicarbonate solution and sat. sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to about 50 ml
  6. additionAbout 100 ml of ether are added to the crystal slurry, which
  7. stirringis then stirred for about 2 h
  8. filtrationfiltered

Sources & evidence

ORD record
ord-24f03be43eff4cf487f4b3fcbe7c91ac
Source dataset
uspto-grants-2005_08
Patent number
US06933295B2

Reaction notes

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