Trifluoroacetic acid → HCID 69377399, compound

HRID 502996Notes

Reaction equation

HRID 502996 reaction equation
F[C:2](F)(F)[C:3](O)=O.C(O[C:13](=O)[NH:14][C:15]([C:18]1[N:22]([CH3:23])[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])=[N:20][N:19]=1)([CH3:17])[CH3:16])(C)(C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:21]1[N:22]([CH3:23])[C:18]([C:15]([N:14]2[CH2:2][C:3]3[C:26](=[CH:25][CH:24]=[CH:29][CH:28]=3)[CH2:13]2)([CH3:16])[CH3:17])=[N:19][N:20]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 131728286HCID 131728286, compound

Product 1

HCID 69377399HCID 69377399, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Trifluoroacetic acid (2 ml) was added to a chloroform (4 ml) solution of tert-Butyl-{1-[5-(2-chlorophenyl)-4-methyl-4H-1,2,4-triazol-3-yl]-1-methylethyl}carbamate (500 mg), followed by stirring at room temperature for 2 hours. The reaction solution and chloroform were added to an aqueous saturated sodium hydrogen carbonate solution and then the organic layer was separated. Furthermore, the organic layer washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered and then the solvent was removed by evaporation under reduced pressure. Potassium carbonate (394 mg) and 1,2-bis(bromomethyl)benzene (376 mg) were added to a DMF (10 ml) solution of the resulting residue, followed by stirring at 60° C. for 14 hours. Distilled water and chloroform were added to the reaction solution and then the organic layer was separated. Furthermore, the organic layer washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting crude product was purified by flash chromatography (chloroform:methanol=25:1) to obtain 35 mg of 2-{1-[5-(2-chlorophenyl)-4-methyl-4H-1,2,4-triazol-3-yl]-1-methylethyl} isoindoline (colorless solid).

Workup

  1. customthe organic layer was separated
  2. washFurthermore, the organic layer washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed by evaporation under reduced pressure
  6. additionPotassium carbonate (394 mg) and 1,2-bis(bromomethyl)benzene (376 mg) were added to a DMF (10 ml) solution of the resulting residue
  7. stirringby stirring at 60° C. for 14 hours
  8. additionDistilled water and chloroform were added to the reaction solution
  9. customthe organic layer was separated
  10. washFurthermore, the organic layer washed with an aqueous saturated sodium chloride solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. customthe solvent was removed by evaporation under reduced pressure
  14. customThe resulting crude product was purified by flash chromatography (chloroform:methanol=25:1)

Sources & evidence

ORD record
ord-cfd7f186d537472f925f9c2b23ffb0c1
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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