Dimethyl Sulfoxide → 1-ethyl-N-[[4-(methylthiomethoxycarbonyl)cyclohexyl]methyl]-1H-pyrazolo[3,4-b]quinolin-4-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]quinoline (3 g), DMSO (9 ml) and trans-4-(aminomethyl)cyclohexane carboxylic acid (4.1 g) is heated at 180° C. overnight. The reaction mixture is then partitioned between CH2Cl2 and water, the layers are separated and the aqueous layer is extracted with CH2Cl2. The organic layers are combined, washed with water, dried over Na2SO4, and evaporated. The residue is purified by column chromatography on silca gel to afford an oil which is crystallized from ether/hexane and then recrystallized from ether/hexane to afford 1-ethyl-N-[[4-(methylthiomethoxycarbonyl)cyclohexyl]methyl]-1H-pyrazolo[3,4-b]quinolin-4-amine, m.p. 135°-136° C.

Provenance & Evidence