Trifluoroacetic acid → HCID 58388029, compound

HRID 2079983Notes

Reaction equation

HRID 2079983 reaction equation
FC(F)(F)C(O)=O.C([O:15][C:16]1[CH:35]=[CH:34][C:19]([CH2:20][NH:21][C:22]([C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[N:30]=[CH:29][CH:28]=[CH:27]3)=[O:23])=[CH:18][CH:17]=1)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1(SC)C=CC=CC=1>[OH:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][NH:21][C:22]([C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[N:30]=[CH:29][CH:28]=[CH:27]3)=[O:23])=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58387946HCID 58387946, compound

Product 1

HCID 58388029HCID 58388029, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 7520ThioanisoleCatalyst

Procedure

Trifluoroacetic acid (5 mL) and thioanisole (3 drops) were added to quinoline-6-carboxylic acid 4-benzyloxybenzylamide (2.67 g, 7.25 mmol) synthesized in Example E-8, the solution was stirred at room temperature for 14 hours, followed by stirring at 50° C. for 4 hours, lastly, and the solution was stirred at 70° C. for 3 hours. The reaction solution was allowed to room temperature, then, was neutralized with an aqueous solution of saturated sodium bicarbonate, extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (ethyl acetate), and the title compound (433 mg, 22%) was obtained as a colorless solid.

Workup

  1. stirringby stirring at 50° C. for 4 hours
  2. stirringlastly, and the solution was stirred at 70° C. for 3 hours
  3. customwas allowed to room temperature
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by NH silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-9de1f7441d0e4b7789297580a47a7c9b
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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