Ammonium Chloride → 1-(Tetrahydro-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-5-ylamine

HRID 1521735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521735
[Cl-].[NH4+].[N+:3]([C:6]1[CH:7]=[C:8]2[CH:14]=[N:13][N:12]([CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:9]2=[N:10][CH:11]=1)([O-])=O>C(O)C.C1COCC1.O.[Fe]>[O:18]1[CH2:17][CH2:16][CH:15]([N:12]2[C:9]3=[N:10][CH:11]=[C:6]([NH2:3])[CH:7]=[C:8]3[CH:14]=[N:13]2)[CH2:20][CH2:19]1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 672364995-Nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine

Produkt 1

HCID 672370741-(Tetrahydro-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-5-ylamineAusbeute 108,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 18504229Ethanol tetrahydrofuran waterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Iron (2.41 g, 42.3 mmol) and ammonium chloride (2.58 g, 48.4 mmol) are added to a solution of 5-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine (3 g, 12 mmol) in ethanol/THF/H2O (4:2:1, 35 mL). The mixture is heated at 100° C. for 2 h. The iron is removed by filtration through pad of Celite® and the filtrate was evaporated under reduced pressure. The residue is purified by flash column chromatography using a gradient of 70% ethyl acetate/petroleum ether to afford the title compound as an off-white solid (2.85 g, 93%).

Aufarbeitung

  1. customThe iron is removed by filtration through pad of Celite®
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue is purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8b093a8708c844c9b397cd58ede26bc6
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073926B2

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