Dimethyl Sulfoxide → 1-ethyl-8-bromo-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 1586180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1586180
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][C:10]=3[Br:17])[CH3:2].CS(C)=O.[CH:22]1([CH2:28][NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:29][CH2:28][CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][C:10]=3[Br:17])[CH3:2]

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 76688CyclohexanemethylamineHCID 212176931-ethyl-4-chloro-8-bromo-1H-pyrazolo[3,4-b]quinoline

Produkt 1

HCID 212176961-ethyl-8-bromo-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amineAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1-ethyl-4-chloro-8-bromo-1H-pyrazolo[3,4-b]quinoline (2.0 g, 6.44 mmol), DMSO (5 ml) and cyclohexylmethylamine (1.46 g, 12.9 mmol) is heated at 80°-90° C. for 3 hours. The reaction mixture is cooled to room temperature and then is poured into water. The resulting solid is collected by filtration, washed with water and evaporated. The residue is purified by column chromatography on silica gel eluting with CH2Cl2 /ether (9/1) to afford 2.0 g (80%) of 1-ethyl-8-bromo-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as a yellow solid, m.p. 160°-162° C.

Aufarbeitung

  1. temperatureis heated at 80°-90° C. for 3 hours
  2. filtrationThe resulting solid is collected by filtration
  3. washwashed with water
  4. customevaporated
  5. customThe residue is purified by column chromatography on silica gel eluting with CH2Cl2 /ether (9/1)

Quellen und Nachweise

ORD-Eintrag
ord-d76d3cf2bcb344f881c1c13fb32af7e6
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05942520

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