4-[3-Oxo-7-(3-[1,2,3]triazol-1-ylprop-1-ynyl)-2H-6-azaisoquinolin-2-ylmethyl]benzoic acid tert-butyl ester → 4-[3-Oxo-7-(3-[1,2,3]triazol-1-ylprop-1-ynyl)-2H-6-azaisoquinolin-2-ylmethyl]benzoic acid

HRID 488789Notes

Reaction equation

HRID 488789 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]=[N:29]4)[N: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][N:28]3[CH:32]=[CH:31][N:30]=[N:29]3)[N:19]=[CH:20]2)=[CH:15][N:14]1[CH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]([OH:33])=[O:5])=[CH:12][CH:11]=1

Participants

3

Reactant 1

HCID 697332714-[3-Oxo-7-(3-[1,2,3]triazol-1-ylprop-1-ynyl)-2H-6-azaisoquinolin-2-ylmethyl]benzoic acid tert-butyl ester

Product 1

HCID 222682364-[3-Oxo-7-(3-[1,2,3]triazol-1-ylprop-1-ynyl)-2H-6-azaisoquinolin-2-ylmethyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-[3-oxo-7-(3-[1,2,3]triazol-1-ylprop-1-ynyl)-2H-6-azaisoquinolin-2-ylmethyl]benzoic acid tert-butyl ester (0.29 g, 0.66 mmol, Example 14A) is treated with trifluoroacetic acid (10 mL) and stirred at room temperature for 40 minutes. The reaction mixture is evaporated to dryness, triturated with ethyl acetate, the solid collect 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 collect by filtration
  4. washwashed with water
  5. washwashed with ethyl acetate
  6. customdried under house vacuum

Sources & evidence

ORD record
ord-1fd0a09435054f63a0a97de8e74a9286
Source dataset
uspto-grants-2005_12
Patent number
US06974822B2

Reaction notes

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