Trifluoroacetic acid → HCID 10318468, compound

HRID 489176Notes

Reaction equation

HRID 489176 reaction equation
C([O:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[N:23]=[CH:22][C:21]3[C:16](=[CH:17][C:18]([C:24]#[C:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:19][CH:20]=3)[C:15]2=[O:33])=[CH:9][CH:8]=1)(C)(C)C.FC(F)(F)C(O)=O>>[O:33]=[C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[C:18]([C:24]#[C:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:17]=2)[CH:22]=[N:23][N:14]1[CH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]([OH:34])=[O:5])=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 9911605HCID 9911605, compound

Product 1

HCID 10318468HCID 10318468, compound

Procedure

A solution of 4-[1-oxo-7-(3-phenyl-prop-1-ynyl)-1H-3-azaisoquinolin-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-a1a89d28b70c4b4c85b67143d798fdab
Source dataset
uspto-grants-2005_12
Patent number
US06977261B2

Reaction notes

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