Dimethyl Sulfoxide → 1-ethyl-7-carboxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 1586161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1586161
[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]=[C:11]([C:17]([OH:19])=[O:18])[CH:10]=3)[CH3:2].CS(C)=O.[CH:24]1([CH2:30][NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.O>C(O)(=O)C>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:31][CH2:30][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[C:11]([C:17]([OH:19])=[O:18])[CH:10]=3)[CH3:2]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 76688CyclohexanemethylamineHCID 212177041-ethyl-4-chloro-7-carboxy-1H-pyrazolo[3,4-b]quinoline

Produkt 1

HCID 212177061-ethyl-7-carboxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 1-ethyl-4-chloro-7-carboxy-1H-pyrazolo[3,4-b]quinoline (0.9 g, 3.3 mmol), DMSO (9 ml) and cyclohexanemethyl amine (0.86 ml, 6.6 mmol) is heated at 120°-130° C. for 6 hours. The reaction mixture is poured into water, acidified with acetic acid and the solid which forms is collected by filtration, dissolved in 5% NaOH and extracted with CH2Cl2 (2×50 ml). The aqueous layer is acidified with acetic acid and the solid that forms is collected by filtration and washed with water. The solid is purified by column chromatography on silica gel eluting with 30% methanol/10% acetic acid/60% CH2Cl2 to afford 1-ethyl-7-carboxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as a yellow solid.

Aufarbeitung

  1. temperatureis heated at 120°-130° C. for 6 hours
  2. filtrationthe solid which forms is collected by filtration
  3. dissolutiondissolved in 5% NaOH
  4. extractionextracted with CH2Cl2 (2×50 ml)
  5. filtrationthe solid that forms is collected by filtration
  6. washwashed with water
  7. customThe solid is purified by column chromatography on silica gel eluting with 30% methanol/10% acetic acid/60% CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-3ada8104b7874a67a64c83ef95b934e8
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05942520

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