HCID 23537502, compound → HCID 178488643, compound

HRID 1792631Notes

Reaction equation

HRID 1792631 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]4[C:20]([C:43]([F:46])([F:45])[F:44])=[N:21][N:22](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:23]=4)[CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]4[C:20]([C:43]([F:45])([F:44])[F:46])=[N:21][NH:22][CH:23]=4)[CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 23537502HCID 23537502, compound

Product 1

HCID 178488643HCID 178488643, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 210 mg 4-(6-methoxypyridin-3-yl)-6-(3-trifluoromethyl-1-trityl-1H-pyrazol-4-yl) quinoline obtained in Example 1063 and 10 mL trifluoroacetic acid was stirred at room temperature for 1 hour. The trifluoroacetic acid was evaporated, and an aqueous saturated sodiumbicarbonate solution was added to the residue which was then extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give 110 mg of the title compound as a colorless solid.

Workup

  1. customThe trifluoroacetic acid was evaporated
  2. additionan aqueous saturated sodiumbicarbonate solution was added to the residue which
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5598c05e55684dffb547e8df1b32f1b8
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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