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

HRID 2283883Notes

Reaction equation

HRID 2283883 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH2:20][CH3:21])[N:8]=[C:9]2[C:18]=1[C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:11]=[C:10]2[NH2:19]>[Pt](=O)=O.FC(F)(F)C(O)=O>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH2:20][CH3:21])[N:8]=[C:9]2[C:18]=1[C:17]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=1[N:11]=[C:10]2[NH2:19]

Participants

4

Reactant 1

HCID 577175141-(4-chlorobutyl)-2-ethyl-2H-pyrazolo[3,4-c]quinolin-4-amine

Product 1

HCID 669581721-(4-chlorobutyl)-2-ethyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amineYield 57.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1-(4-chlorobutyl)-2-ethyl-2H-pyrazolo[3,4-c]quinolin-4-amine (3 g, prepared as described in Example 19), platinum (IV) oxide (3 g), and trifluoroacetic acid (50 mL) was placed under hydrogen pressure (50 psi, 3.4×105 Pa) on a Parr shaker for 2 days. The reaction mixture was filtered through a layer of CELITE filter agent and the filter cake was rinsed with dichloromethane. The filtrate was concentrated under reduced pressure. The residue was made basic (p H 14) by the addition of 50% sodium hydroxide and then extracted with chloroform. The extract was dried over sodium sulfate and then purified by chromatography on a HORIZON HPFC system (eluting with chloroform/CMA in a gradient from 100:0 to 70:30) to provide 1.75 g of 1-(4-chlorobutyl)-2-ethyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amine as a light yellow solid.

Workup

  1. customfor 2 days
  2. filtrationThe reaction mixture was filtered through a layer of CELITE filter agent
  3. washthe filter cake was rinsed with dichloromethane
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionby the addition of 50% sodium hydroxide
  6. extractionextracted with chloroform
  7. dry with materialThe extract was dried over sodium sulfate
  8. custompurified by chromatography on a HORIZON HPFC system (
  9. washeluting with chloroform/CMA in a gradient from 100:0 to 70:30)

Sources & evidence

ORD record
ord-d0fa1500b9464e0fa684edef4b2472aa
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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