Benzyl Alcohol → 4-(Benzyloxy)-N,3-dimethyl-N-phenyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

HRID 497955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 497955
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[C:17]([C:18]([N:20]([CH3:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])=[CH:16][N:15]=[C:14]2[N:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[N:29]=[C:30]([CH3:31])[C:13]=12>CN(C)C=O>[CH2:1]([O:8][C:12]1[C:17]([C:18]([N:20]([CH3:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:19])=[CH:16][N:15]=[C:14]2[N:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[N:29]=[C:30]([CH3:31])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 223202774-Chloro-N,3-dimethyl-N-phenyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

Produkt 1

HCID 223201084-(Benzyloxy)-N,3-dimethyl-N-phenyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of benzyl alcohol (0.40 g, 3.7 mmol) in N,N-dimethylformamide (10 mL), sodium hydride (0.16 g, 40 mmol, 60% oil) was added at room temperature, and the resulting mixture was stirred at the same temperature for 30 minutes. To the solution, a solution of 4-chloro-N,3-dimethyl-N-phenyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide (1.0 g, 2.8 mmol) in N,N-dimethylformamide (10 mL) solution was added at room temperature, and stirred at 100° C. for 11.5 hours. The mixture was concentrated under reduced pressure, and the residue was poured into water. Organic matter was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Purification of the resulting residue by silica gel chromatography (hexane:chloroform:ethyl acetate=2:1:1 to 1:1:1 to 1:2:2) gave the title compound (0.99 g, 80% yield).

Aufarbeitung

  1. stirringstirred at 100° C. for 11.5 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionthe residue was poured into water
  4. extractionOrganic matter was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customPurification of the resulting residue by silica gel chromatography (hexane:chloroform:ethyl acetate=2:1:1 to 1:1:1 to 1:2:2)

Quellen und Nachweise

ORD-Eintrag
ord-cd05fcc741aa4ebb9bf785ec09390e63
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949648B2

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