Trifluoroacetic acid → 4-[7-(3-Imidazol-1-ylprop-1-ynyl)-3-oxo-2H-isoquinolin-2-ylmethyl]benzoic Acid

HRID 488787Notes

Reaction equation

HRID 488787 reaction equation
C([O:5][C:6](=[O:33])[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][N:28]4[CH:32]=[CH:31][N: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>>[N:28]1([CH2:27][C:26]#[C:25][C:18]2[CH:19]=[CH:20][C:21]3[C:16]([CH:17]=2)=[CH:15][N:14]([CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:33])=[O:5])=[CH:8][CH:9]=2)[C:23](=[O:24])[CH:22]=3)[CH:32]=[CH:31][N:30]=[CH:29]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 104783554-[7-(3-Imidazol-1-ylprop-1-ynyl)-3-oxo-2H-isoquinolin-2-ylmethyl]benzoic Acid tert-butyl Ester

Product 1

HCID 104076004-[7-(3-Imidazol-1-ylprop-1-ynyl)-3-oxo-2H-isoquinolin-2-ylmethyl]benzoic Acid

Procedure

A solution of 4-[7-(3-imidazol-1-ylprop-1-ynyl)-3-oxo-2H-isoquinolin-2-ylmethyl]benzoic acid tert-butyl ester (0.38 g, 0.86 mmol, Example 13A) is treated with trifluoroacetic acid (6 mL) and stirred at room temperature for 30 minutes. The reaction mixture is evaporated to dryness, triturated with ethyl acetate, the solid is collected by filtration, washed with water, washed with ethyl acetate, and dried under house vacuum. This will afford the desired product.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. customtriturated with ethyl acetate
  3. filtrationthe solid is collected by filtration
  4. washwashed with water
  5. washwashed with ethyl acetate
  6. customdried under house vacuum

Sources & evidence

ORD record
ord-dc691778348542bb8cbfcc3ea7488fcf
Source dataset
uspto-grants-2005_12
Patent number
US06974822B2

Reaction notes

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