Hydrochloric Acid → 1-ethyl-3-methyl-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine hydrochloride

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-1-ethyl-3-methyl-1H-pyrazolo[3,4-b]quinoline (1.0 g, 0.0043 mmol), cyclohexanemethylamine (1.2 ml, 0.009 mol) and DMSO (3 ml) is heated at 80° C. overnight. The reaction mixture is pured into water (100 ml)/NH4OH (0.5 ml) and is extracted with CH2Cl2. The solvent is evaporated to about 20 ml and then the mixture is purified by chromatography on silica gel, followed by high pressure liquid chromatography eluting with 20% EtOAc/hexane to 50% EtOAc/hexane to afford the product as the free base. The free base is dissolved in CH2Cl2 (20 ml) and treated with ethereal HCl and the solution is evaporated. The residue is crystallized from ethyl acetate/ether/ethanol to afford 1-ethyl-3-methyl-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine hydrochloride, m.p. 215°-217° C.

Provenance & Evidence