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

HRID 1360522

반응식

HRID 1360522 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 82844Platinum oxide (PtO)촉매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b6a3ad4fa4e9459b95c110cc18630be5
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879849B2

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