Hydrogen Peroxide → 2-(Ethylamino)-4-{3-isopropyl-4-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzamide

HRID 1625251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1625251
[CH2:1]([NH:3][C:4]1[CH:11]=[C:10]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][C:20]([N:21]4[CH:25]=[C:24]([C:26]5[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=5)[N:23]=[CH:22]4)=[C:15]3[C:14]([CH:32]([CH3:34])[CH3:33])=[N:13]2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])[CH3:2].[OH:35]O.[OH-].[Na+].O>CS(C)=O>[CH2:1]([NH:3][C:4]1[CH:11]=[C:10]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][C:20]([N:21]4[CH:25]=[C:24]([C:26]5[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=5)[N:23]=[CH:22]4)=[C:15]3[C:14]([CH:32]([CH3:33])[CH3:34])=[N:13]2)[CH:9]=[CH:8][C:5]=1[C:6]([NH2:7])=[O:35])[CH3:2]

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 675006162-(ethylamino)-4-{3-isopropyl-4-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile

Produkt 1

HCID 675025942-(Ethylamino)-4-{3-isopropyl-4-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Compound (100b) (1.00 g), copper iodide (0.248 g), cesium carbonate (2.12 g), and 4-bromo-2-(ethylamino)benzonitrile (0.932 g) were suspended in 1,4-dioxane (10 mL), and N,N′-dimethylethylenediamine (0.560 mL) was added to the suspension, followed by stirring at 150° C. for 20 hr. The reaction solution was distributed between chloroform and water. The organic layer was washed with a 2 N aqueous sodium hydroxide solution and dried over magnesium sulfate, and then the solvent was distilled away. The residue was purified by neutral silica gel column chromatography (chloroform/methanol) to obtain 2-(ethylamino)-4-{3-isopropyl-4-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile (1.13 g, 77%) as a white solid. 2-(Ethylamino)-4-{3-isopropyl-4-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile (0.700 g) was dissolved in DMSO (10 mL), and a 30% hydrogen peroxide solution (0.310 mL) and a 4 N aqueous sodium hydroxide solution (1.16 mL) were added to the resulting solution, followed by stirring at room temperature for 10 min. Water was added to the reaction solution, and the precipitate was collected by filtration and was dried under reduced pressure to obtain compound (109) (0.655 g, 90%) as a white solid.

Aufarbeitung

  1. filtrationthe precipitate was collected by filtration
  2. customwas dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ef1f9e92de2c4c48b11de777001aa1d7
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08779142B2

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