Trifluoroacetic anhydride → HCID 58244070, compound

HRID 389146Notes

Reaction equation

HRID 389146 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][C:17]([CH3:35])([C:19]2[N:23]([CH3:24])[C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])=[N:21][N:20]=2)[CH3:18])=[C:6]([C:8]2[O:9][CH:10]=[C:11]([C:13](O)=O)[N:12]=2)[CH:7]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C1CCN2C(=[N:55]CCC2)CC1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>C(N(CC)CC)C.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][C:17]([CH3:18])([C:19]2[N:23]([CH3:24])[C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:32])[F:33])=[N:21][N:20]=2)[CH3:35])=[C:6]([C:8]2[O:9][CH:10]=[C:11]([C:13]#[N:55])[N:12]=2)[CH:7]=1

Participants

8

Reactant 5

HCID 9845Trifluoroacetic anhydride2×HCID 67749Trifluoromethanesulfonic anhydrideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 58243487HCID 58243487, compound

Product 1

HCID 58244070HCID 58244070, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Procedure

2-[5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)phenyl]-1,3-oxazole-4-carboxylic acid (375 mg) was mixed with dichloromethane (10 ml), and triethylamine (0.52 ml) was added, followed by ice-cooling and addition of trifluoromethanesulfonic anhydride (0.316 ml). After stirring at room temperature overnight, it was further stirred at 40° C. for 3 hours. DBU (0.222 ml) was added to the reaction solution, followed by stirring for one hour. Trifluoroacetic anhydride was added to the reaction solution, followed by stirring at 40° C. for 3 hours, and trifluoroacetic anhydride (0.158 ml) and triethylamine (0.52 ml) were added thereto, followed by stirring at 40° C. for one hour. The reaction solution was cooled to room temperature and saturated aqueous sodium bicarbonate was added thereto, followed by extraction with chloroform. The organic layer was washed with water and then saturated brine in this order, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=200:1), and the resulting residue was washed with diisopropylether to obtain, as a beige solid, 2-[5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)phenyl]-1,3-oxazole-4-carbonitrile (190 mg).

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringit was further stirred at 40° C. for 3 hours
  4. stirringby stirring for one hour
  5. stirringby stirring at 40° C. for 3 hours
  6. stirringby stirring at 40° C. for one hour
  7. temperatureThe reaction solution was cooled to room temperature
  8. extractionfollowed by extraction with chloroform
  9. washThe organic layer was washed with water
  10. dry with materialsaturated brine in this order, dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (chloroform:methanol=200:1)
  13. washthe resulting residue was washed with diisopropylether

Sources & evidence

ORD record
ord-ec3baf205196474a824433a34859dee5
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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