1,2-Dichloroethane → 7-(3,5-dimethylisoxazol-4-yl)-N-ethyl-8-methoxy-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-imidazo[4,5-c]quinolin-2-amine

Participants

Reaction Conditions

Reaction Steps

7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-N4-((tetrahydro-2H-pyran-4-yl)methyl)quinoline-3,4-diamine (for a preparation see Intermediate 17) (100 mg, 0.261 mmol) was dissolved in methanol and ethyl isothiocyanate (45.6 mg, 0.523 mmol) was added. The mixture was heated at 50° C. for 6 h, cooled and evaporated in vacuo to give a beige solid residue. This was re-dissolved in THF (5 ml) and EDC (100 mg, 0.523 mmol) was added, then the mixture heated at 60° C. overnight. The solvent was evaporated in vacuo and the residue dissolved in DCM (10 ml) and washed with water (10 ml), the organic layer dried and evaporated and the residue dissolved in DCM (2 ml) and loaded onto a 10 g silica column, then eluted with 2M methanolic ammonia/DCM (0-10%) and product-containing fractions evaporated in vacuo to give 7-(3,5-dimethylisoxazol-4-yl)-N-ethyl-8-methoxy-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-imidazo[4,5-c]quinolin-2-amine (37 mg, 0.085 mmol, 32.5% yield) as a colourless glass. LCMS (formate) Rt 0.71 min, MH+ 436

Provenance & Evidence