2H-Pyrazolo[3,4-c]quinolin-4-amine, 1-(2-methylpropyl)-2-propyl- → 1-(2-methylpropyl)-2-propyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amine

HRID 1360464Notes

Reaction equation

HRID 1360464 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][C:4]1[N:5]([CH2:18][CH2:19][CH3:20])[N:6]=[C:7]2[C:16]=1[C:15]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:9]=[C:8]2[NH2:17]>FC(F)(F)C(O)=O.C(Cl)(Cl)Cl.CO.[Pt](=O)=O>[CH3:1][CH:2]([CH3:21])[CH2:3][C:4]1[N:5]([CH2:18][CH2:19][CH3:20])[N:6]=[C:7]2[C:16]=1[C:15]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=1[N:9]=[C:8]2[NH2:17]

Participants

6

Reactant 1

HCID 112775352H-Pyrazolo[3,4-c]quinolin-4-amine, 1-(2-methylpropyl)-2-propyl-

Product 1

HCID 577175751-(2-methylpropyl)-2-propyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amineYield 64%

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-(2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine (0.8 g, 3 mmol), prepared as described in Example 1, 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 on a Parr apparatus. The reaction mixture was diluted with chloroform (20 mL) and methanol (10 mL) and filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure. The residue was suspended in 6 M aqueous hydrochloric acid (5 mL), stirred for 30 minutes, and treated with 50% aqueous sodium hydroxide to adjust the mixture to pH 13. A precipitate formed and was isolated by filtration, washed with water, and dried. The crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-35% CMA in chloroform) to yield 0.55 g of 1-(2-methylpropyl)-2-propyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amine as an off-white powder, mp 167-168° C.

Workup

  1. filtrationfiltered through a layer of CELITE filter agent
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. stirringstirred for 30 minutes
  4. additiontreated with 50% aqueous sodium hydroxide
  5. customA precipitate formed
  6. customwas isolated by filtration
  7. washwashed with water
  8. customdried
  9. customThe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-35% CMA in chloroform)

Sources & evidence

ORD record
ord-cc84b88624434bf5ba84fcae7cd14628
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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