Trifluoroacetic acid → HCID 66958538, compound

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

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.