4-[1-oxo-7-(3-[1,2,3]Triazol-1-ylprop-1-ynyl)-1H-6-azaisoquinolin-2-ylmethyl]benzoic Acid tert-Butyl Ester → 4-[1-oxo-7-(3-[1,2,3]Triazol-1-ylprop-1-ynyl)-1H-6-azaisoquinolin-2-ylmethyl]benzoic Acid

HRID 489188Notes

Reaction equation

HRID 489188 reaction equation
C([O:5][C:6](=[O:33])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][C:18]([C:24]#[C:25][CH2:26][N:27]4[CH:31]=[CH:30][N:29]=[N:28]4)=[N:19][CH: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](=[CH:20][N:19]=[C:18]([C:24]#[C:25][CH2:26][N:27]3[CH:31]=[CH:30][N:29]=[N:28]3)[CH:17]=2)[CH:22]=[CH:23][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 102527494-[1-oxo-7-(3-[1,2,3]Triazol-1-ylprop-1-ynyl)-1H-6-azaisoquinolin-2-ylmethyl]benzoic Acid tert-Butyl Ester

Product 1

HCID 100001484-[1-oxo-7-(3-[1,2,3]Triazol-1-ylprop-1-ynyl)-1H-6-azaisoquinolin-2-ylmethyl]benzoic Acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-[1-oxo-7-(3-[1,2,3]triazol-1-ylprop-1-ynyl)-1H-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-b69f7e96baf54a54ad75a4f15dc9c629
Source dataset
uspto-grants-2005_12
Patent number
US06977261B2

Reaction notes

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