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

HRID 2283845Notes

Reaction equation

HRID 2283845 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH3:20])[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].FC(F)(F)C(O)=O>[Pt]=O>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH3:20])[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 2

HCID 6422Trifluoroacetic acidHCID 577175021-(4-chlorobutyl)-2-methyl-2H-pyrazolo[3,4-c]quinolin-4-amine

Product 1

HCID 669586211-(4-chlorobutyl)-2-methyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amineYield 79.4%

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

A mixture of 1-(4-chlorobutyl)-2-methyl-2H-pyrazolo[3,4-c]quinoline-4-amine (2.8 g, 8.6 mmol, prepared as described in Part F of Examples 454-488), platinum oxide, and trifluoroacetic acid was shaken under hydrogen pressure on a Parr apparatus 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), the pH was adjusted to pH 12 with 50% sodium hydroxide, and the mixture was extracted with dichloromethane. The extracts were dried over sodium sulfate and concentrated under reduce pressure. The residue was purified by chromatography on a HORIZON HPFC system (40+M cartridge eluting with a gradient of 0 to 20% CMA in chloroform) to provide 2.0 g of 1-(4-chlorobutyl)-2-methyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinoline-4-amine as a yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through a layer of CELITE filter agent
  2. washthe filter cake was rinsed with methanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionThe residue was diluted with water (10 mL)
  5. extractionthe mixture was extracted with dichloromethane
  6. dry with materialThe extracts were dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on a HORIZON HPFC system (40+M cartridge
  9. washeluting with a gradient of 0 to 20% CMA in chloroform)

Sources & evidence

ORD record
ord-ea21425c7ea4462688e9744d85a5abfc
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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