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

HRID 2283885Notes

Reaction equation

HRID 2283885 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:8]([CH3:21])[N:9]=[C:10]2[C:19]=1[C:18]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:12]=[C:11]2[NH2:20].FC(F)(F)C(O)=O>[Pt](=O)=O>[Cl:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:8]([CH3:21])[N:9]=[C:10]2[C:19]=1[C:18]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=1[N:12]=[C:11]2[NH2:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 669591321-(4-chlorobutyl)-2-methyl-2H-pyrazolo[3,4-c]quinolin-4-amine hydrochloride

Product 1

HCID 669586211-(4-chlorobutyl)-2-methyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amineYield 79.3%

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

A mixture of 1-(4-chlorobutyl)-2-methyl-2H-pyrazolo[3,4-c]quinolin-4-amine hydrochloride (2.8 g, prepared as described in Examples 454-488), platinum (IV) oxide (2.1 g), and trifluoroacetic acid (43 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 methanol. The filtrate was concentrated under reduced pressure. The residue was diluted with water (10 mL), made basic (pH 14) by the addition of 50% sodium hydroxide and then extracted with dichloromethane. The extract was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a HORIZON HPFC system (40+M cartridge eluting with chloroform/CMA in a gradient from 100:0 to 80:20) to provide 2.0 g of 1-(4-chlorobutyl)-2-methyl-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 methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionThe residue was diluted with water (10 mL)
  6. additionby the addition of 50% sodium hydroxide
  7. extractionextracted with dichloromethane
  8. dry with materialThe extract was dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by chromatography on a HORIZON HPFC system (40+M cartridge
  11. washeluting with chloroform/CMA in a gradient from 100:0 to 80:20)

Sources & evidence

ORD record
ord-3afbf26d45f74c3880a7e1332cdb6633
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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