4-Heptanone → [7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl](1-propylbutyl)amine

HRID 2113793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2113793
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2=[C:16]([NH2:20])[N:17]([CH3:19])[N:18]=[C:11]12.[CH3:21][CH2:22][CH2:23][C:24](=O)[CH2:25][CH2:26][CH3:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2=[C:16]([NH:20][CH:24]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:22][CH3:21])[N:17]([CH3:19])[N:18]=[C:11]12

Komponenten

5

Edukt 3

HCID 312464-Heptanone2×HCID 5049666Sodium triacetoxyborohydride2×HCID 221362787-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine

Produkt 1

HCID 22136272[7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl](1-propylbutyl)amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

7-(2-Chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine (5-45; 45.7 mg) and 4-heptanone (24 μL) were dissolved and stirred in 3 mL of dichloroethane. After 15 min, 44.5 mg of sodium triacetoxyborohydride was added. The reaction mixture was stirred at 60° C. during the day and at room temperature over night during 3 d. During this period, an additional 109 μL of 4-heptanone and an additional 104 mg of sodium triacetoxyborohydride were added to drive the reaction to completion. The reaction mixture was then partitioned between ethyl acetate and water. The ethyl acetate was dried with magnesium sulfate and evaporated. The crude product was chromatographed on silica gel eluting with an acetone/hexane gradient to provide 11 mg of crystalline [7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl](1-propylbutyl)amine (5-6): ms (MH+)=389.

Aufarbeitung

  1. waitDuring this period
  2. customthe reaction to completion
  3. customThe reaction mixture was then partitioned between ethyl acetate and water
  4. dry with materialThe ethyl acetate was dried with magnesium sulfate
  5. customevaporated
  6. customThe crude product was chromatographed on silica gel eluting with an acetone/hexane gradient

Quellen und Nachweise

ORD-Eintrag
ord-b2d9520e622d4452b03569f78341784b
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07432283B2

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