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

HRID 1360522

Reaktionsgleichung

Reaktionsgleichung von HRID 1360522
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 669586211-(4-chlorobutyl)-2-methyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amineAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 82844Platinum oxide (PtO)Katalysator

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b6a3ad4fa4e9459b95c110cc18630be5
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879849B2

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