HCID 66980605, compound → HCID 56952352, compound

HRID 1844512Notes

Reaction equation

HRID 1844512 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:31](C)[C:32](=O)OC(C)(C)C)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:30])[C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)=[CH:11][N:10]=1>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[C:4]([NH:31][CH3:32])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[N:10]=[CH:11][C:12]([NH:15][C:16](=[O:30])[C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:21][CH:22]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 66980605HCID 66980605, compound

Product 1

HCID 56952352HCID 56952352, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl [3-fluoro-4-({5-[(4-phenoxybenzoyl)amino]pyridin-2-yl}oxy)phenyl]-methylcarbamate (0.53 g) was dissolved in TFA (4 mL) and stirred at room temperature for 5 min. The mixture was evaporated under reduced pressure and the residue was dissolved in AcOEt. Ice cold 5 M NaOH was added to adjust the pH to 12, and the mixture was extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was dissolved in Et2O, and the solution was stirred for 1 day. The resulting precipitate was collected and washed with Et2O to give the title compound as a white powder (0.29 g).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in AcOEt
  3. additionIce cold 5 M NaOH 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 MgSO4
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue was dissolved in Et2O
  9. stirringthe solution was stirred for 1 day
  10. customThe resulting precipitate was collected
  11. washwashed with Et2O

Sources & evidence

ORD record
ord-9ae12593ce7842b881a95673555de1b1
Source dataset
uspto-grants-2015_02
Patent number
US08946437B2

Reaction notes

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