Citric Acid → N-[7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]propionamide

HRID 2113794

Reaktionsgleichung

Reaktionsgleichung von HRID 2113794
[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.C(N(CC)CC)C.[C:28](Cl)(=[O:31])[CH2:29][CH3:30].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[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][C:28](=[O:31])[CH2:29][CH3:30])[N:17]([CH3:19])[N:18]=[C:11]12

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 221362787-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine

Produkt 1

HCID 22136285N-[7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine (5-45; 0.51 g) and triethylamine (0.27 mL) in dichloromethane (40 mL) cooled to 0° C. was added dropwise over 25 minutes a solution of propionyl chloride (0.17 mL) in dichloromethane (10 mL). The resulting mixture was stirred for an additional 1 h at 0° C., followed by 14 h at room temperature. The reaction mixture was stirred with an aqueous 5% citric acid solution (40 mL) for 10 minutes. The layers were separated, and the aqueous layer was further extracted with dichloromethane (50 mL). The combined organic extracts were dried over anhydrous sodium sulfate, decanted from the desiccating agent and concentrated in vacuo. The resulting residue was purified by silica gel chromatography using a dichloromethane/methanol gradient to afford N-[7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]propionamide (7-6; 0.49 g) as an off white solid: ms (MH+)=347.

Aufarbeitung

  1. waitfollowed by 14 h at room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with dichloromethane (50 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. customdecanted from the desiccating agent
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-326e8be4b5534630b4ad9660aacfb6ba
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07432283B2

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