Triethylamine → HCID 59389277, compound

HRID 2357897Notes

Reaction equation

HRID 2357897 reaction equation
[CH2:1]([C:3]1[CH:13]=[C:6]2[C:7]([OH:12])=[CH:8][C:9]([F:11])=[CH:10][N:5]2[N:4]=1)[CH3:2].C(N(CC)CC)C.[F:21][C:22]([F:28])([F:27])[S:23](O)(=[O:25])=[O:24]>ClCCl>[CH2:1]([C:3]1[CH:13]=[C:6]2[C:7]([O:12][S:23]([C:22]([F:28])([F:27])[F:21])(=[O:25])=[O:24])=[CH:8][C:9]([F:11])=[CH:10][N:5]2[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 59389363HCID 59389363, compound

Product 1

HCID 59389277HCID 59389277, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Example 46 (2.88 g) was dissolved in dichloromethane (100 mL). To this solution, triethylamine (4.51 mL) was added, followed by addition of anhydrous trifluoromethanesulfonic acid (2.97 mL) at 0° C. The mixture was stirred at room temperature for 1 hour. Subsequently, the reaction was terminated by adding water and the mixture was extracted three times with ethylacetate. The organic layer was washed with saturated brine and dried over sodium sulfate. Evaporation of the solvent under reduced pressure and purification by silica gel column chromatography (hexane:ethyl acetate=20:1) afforded the title compound as a yellow oil (4.25).

Workup

  1. customSubsequently, the reaction was terminated
  2. additionby adding water
  3. extractionthe mixture was extracted three times with ethylacetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvent
  7. customunder reduced pressure and purification by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-48ea273286dc45ba9cae276d2851ebb9
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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