Trifluoroacetic acid → 4-[3-Oxo-7-(3-phenyl-prop-1-ynyl)-2H-isoquinolin-2-ylmethyl]benzoic Acid

HRID 488774Notes

Reaction equation

HRID 488774 reaction equation
C([O:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:23](=[O:24])[CH:22]=[C:21]3[C:16]([CH:17]=[C:18]([C:25]#[C:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:19]=[CH:20]3)=[CH:15]2)=[CH:9][CH:8]=1)(C)(C)C.FC(F)(F)C(O)=O>>[O:24]=[C:23]1[CH:22]=[C:21]2[C:16]([CH:17]=[C:18]([C:25]#[C:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:19]=[CH:20]2)=[CH:15][N:14]1[CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([OH:34])=[O:5])=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 99334174-[3-Oxo-7-(3-phenyl-prop-1-ynyl)-2H-isoquinolin-2-ylmethyl]benzoic Acid tert-butyl Ester

Product 1

HCID 100691404-[3-Oxo-7-(3-phenyl-prop-1-ynyl)-2H-isoquinolin-2-ylmethyl]benzoic Acid

Procedure

A solution of 4-[3-oxo-7-(3-phenyl-prop-1-ynyl)-2H-isoquinolin-2-ylmethyl]benzoic acid tert-butyl ester [0.20 g, 0.44 mmol, Example 1A, Step (2)] is treated with trifluoroacetic acid (5 mL) and the reaction mixture stirred at room temperature for 30 minutes. The solution is evaporated to dryness, the residue is dissolved in ethyl acetate, washed with water, brine, dried over MgSO4 and evaporated to dryness. The brown solid is triturated with acetonitrile, the solid collected by filtration, and washed with acetonitrile. The solid is then dissolved in hot ethyl acetate, evaporated onto silica gel, and purified on a 2.5×10 cm silica gel column eluted with hexanes/ethyl acetate 1:1, followed by ethyl acetate. Drying will afford the purified product.

Workup

  1. customThe solution is evaporated to dryness
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe brown solid is triturated with acetonitrile
  7. filtrationthe solid collected by filtration
  8. washwashed with acetonitrile
  9. dissolutionThe solid is then dissolved in hot ethyl acetate
  10. customevaporated onto silica gel
  11. custompurified on a 2.5×10 cm silica gel column
  12. washeluted with hexanes/ethyl acetate 1:1
  13. customDrying will
  14. customafford the purified product

Sources & evidence

ORD record
ord-57bdeb1eb66c446b90f90539b12bb190
Source dataset
uspto-grants-2005_12
Patent number
US06974822B2

Reaction notes

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