Trifluoroacetic acid → HCID 56952644, compound

HRID 1844513Notes

Reaction equation

HRID 1844513 reaction equation
[CH3:1][N:2]([C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[CH:19][N:18]=2)=[C:12]([CH3:36])[CH:11]=1)C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:36][C:12]1[CH:11]=[C:10]([NH:2][CH3:1])[CH:15]=[CH:14][C:13]=1[O:16][C:17]1[N:18]=[CH:19][C:20]([NH:23][C:24](=[O:35])[C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86698879HCID 86698879, compound

Product 1

HCID 56952644HCID 56952644, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl methyl{3-methyl-4-[(5-{[4-(trifluoromethyl)benzoyl]amino}pyridin-2-yl)oxy]phenyl}carbamate (0.60 g) in CH2Cl2 (1 mL) was added TFA (3.32 mL) in three portion at 0° C. After stirring at 0° C. for 30 min, the mixture was evaporated under reduced pressure and the residue was dissolved in AcOEt. Ice cold 2 M NaOH (10 mL) was added, the mixture was extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. After addition of Et2O (20 mL), the solution was stirred vigorously. The resulting precipitate was collected and the precipitate was recrystallized from Et2O/AcOEt/Hexane to afford the title compound (0.44 g) as a white powder.

Workup

  1. customthe mixture was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in AcOEt
  3. additionIce cold 2 M NaOH (10 mL) was added
  4. extractionthe mixture was extracted with AcOEt
  5. washThe organic layer was washed with water and saturated aqueous NaCl
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. additionAfter addition of Et2O (20 mL)
  9. stirringthe solution was stirred vigorously
  10. customThe resulting precipitate was collected
  11. customthe precipitate was recrystallized from Et2O/AcOEt/Hexane

Sources & evidence

ORD record
ord-eb6ba5a16f2b45f1abd2b6f869f586be
Source dataset
uspto-grants-2015_02
Patent number
US08946437B2

Reaction notes

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