4-[1-oxo-7-(3-[1,2,4]Triazol-1-ylprop-1-ynyl)-1H-3,5,8-triazaisoquinolin-2-ylmethyl]benzoic Acid tert-Butyl Ester → 4-[1-oxo-7-(3-[1,2,4]Triazol-1-ylprop-1-ynyl)-1H-3,5,8-triazaisoquinolin-2-ylmethyl]benzoic Acid

HRID 489190Notes

Reaction equation

HRID 489190 reaction equation
C([O:5][C:6](=[O:33])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[N:23]=[CH:22][C:21]3[C:16](=[N:17][C:18]([C:24]#[C:25][CH2:26][N:27]4[CH:31]=[N:30][CH:29]=[N:28]4)=[CH:19][N:20]=3)[C:15]2=[O:32])=[CH:9][CH:8]=1)(C)(C)C>FC(F)(F)C(O)=O>[O:32]=[C:15]1[C:16]2[C:21](=[N:20][CH:19]=[C:18]([C:24]#[C:25][CH2:26][N:27]3[CH:31]=[N:30][CH:29]=[N:28]3)[N:17]=2)[CH:22]=[N:23][N:14]1[CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([OH:33])=[O:5])=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 104111454-[1-oxo-7-(3-[1,2,4]Triazol-1-ylprop-1-ynyl)-1H-3,5,8-triazaisoquinolin-2-ylmethyl]benzoic Acid tert-Butyl Ester

Product 1

HCID 222652984-[1-oxo-7-(3-[1,2,4]Triazol-1-ylprop-1-ynyl)-1H-3,5,8-triazaisoquinolin-2-ylmethyl]benzoic Acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-[1-oxo-7-(3-[1,2,4]triazol-1-ylprop-1-ynyl)-1H-3,5,8-triazaisoquinolin-2-ylmethyl]benzoic acid tert-butyl ester (0.46 g, 1.04 mmol, Example 15A) 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 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-2cc3e9b88c184c3c9dd6dbd5d9b44078
Source dataset
uspto-grants-2005_12
Patent number
US06977261B2

Reaction notes

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