Trifluoroacetic acid → HCID 66958538, compound

HRID 1984346Notes

Reaction equation

HRID 1984346 reaction equation
[CH3:1][N:2]1[C:14]([CH2:15][CH:16]([CH3:18])[CH3:17])=[C:13]2[C:4]([C:5]([NH2:19])=[N:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=32)=[N:3]1.[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23]>C(Cl)(Cl)Cl.[Pt](=O)=O>[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23].[CH3:1][N:2]1[C:14]([CH2:15][CH:16]([CH3:17])[CH3:18])=[C:13]2[C:4]([C:5]([NH2:19])=[N:6][C:7]3[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=32)=[N:3]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 669586022-Methyl-1-(2-methylpropyl)-2H-pyrazolo[3,4-c]quinolin-4-amine

Product 1

HCID 66958538HCID 66958538, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 2-methyl-1-(2-methylpropyl)-2H-pyrazolo[3,4-c]quinolin-4-amine (0.6 g, 2 mmol), prepared as described in Example 3, in trifluoroacetic acid (10 mL) was treated with platinum (IV) oxide (0.5 g) and shaken under hydrogen pressure (50 psi, 3.4×105 Pa) for 24 hours. The reaction mixture was diluted with chloroform (20 mL) and filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure and dissolved in chloroform (50 mL). The solution was adjusted to pH 12 with the addition of ammonium hydroxide and stirred for 20 minutes. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was recrystallized from acetonitrile to provide 0.3 g of 2-methyl-1-(2-methylpropyl)-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amine trifluoroacetate as a white powder, mp 204-206° C.

Workup

  1. filtrationfiltered through a layer of CELITE filter agent
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. dissolutiondissolved in chloroform (50 mL)
  4. additionThe solution was adjusted to pH 12 with the addition of ammonium hydroxide
  5. stirringstirred for 20 minutes
  6. customThe organic layer was separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b065699d68f24ad29797c910a33974f5
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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