Water → Ethyl 4-[(4-methoxybenzenesulfonyl)pyridin-3-ylmethylamino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 1266320

Reaktionsgleichung

Reaktionsgleichung von HRID 1266320
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[H-].[Na+].Cl[C:23]1[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][N:26]=[C:25]2[N:34]([CH3:38])[N:35]=[C:36]([CH3:37])[C:24]=12.O>CN1CCCC1=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C:23]2[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][N:26]=[C:25]3[N:34]([CH3:38])[N:35]=[C:36]([CH3:37])[C:24]=23)(=[O:10])=[O:11])=[CH:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 8097404-methoxy-N-(pyridin-3-ylmethyl)benzenesulfonamideHCID 2736380ethyl 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Produkt 1

HCID 12044790Ethyl 4-[(4-methoxybenzenesulfonyl)pyridin-3-ylmethylamino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylateAusbeute 57,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Versuchsvorschrift

To a solution of 1.39 g (5 mmol) of (4-methoxybenzenesulfonyl)(3-pyridinylmethyl) amine in 4 ml of anhydrous 1-methyl-2-pyrrolidinone was added 0.2 g (5 mmol) of sodium hydride (60% in oil) and the mixture stirred at room temperature until gas evolution ceased. To this mixture was added 1.15 g (4.54 mmol) of ethyl 4-chloro-1,3-dimethylpyrazolo[3,4-b]pyridine-5-carboxylate and 2 ml of anhydrous 1-methyl-2-pyrrolidinone. The mixture was stirred in a sealed tube under nitrogen in an oil bath at 90° C. for 3 days. The mixture was cooled, poured into water and extracted with ethyl acetate. The extract was washed with H2O, brine and dried (Na2SO4). The solution was filtered through a thin pad of hydrous magnesuim silicate and the filter pad washed with ethyl acetate. The filtrate was concentrated to dryness under vacuum to give 1.3 g of solid. Chromatography on silica gel with ethyl acetate as solvent gave 0.35 g of product as a solid, mp 152-154° C.

Aufarbeitung

  1. stirringThe mixture was stirred in a sealed tube under nitrogen in an oil bath at 90° C. for 3 days
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationThe solution was filtered through a thin pad of hydrous magnesuim silicate
  7. washthe filter pad washed with ethyl acetate
  8. concentrationThe filtrate was concentrated to dryness under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1d02624010eb47a3a6b42aaddf4c3358
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06548524B2

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