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

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To a solution of 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4—((R)-1-(pyridin-2-yl)ethyl)quinoline-3,4-diamine (for a preparation, see Intermediate 25) (538 mg, 1.38 mmol) in EtOH (40 mL) was added 1-isothiocyanato-2-methoxyethane (0.30 mL, 2.76 mmol) and the mixture heated at 60° C. for 5.5 h. A further portion of 1-isothiocyanato-2-methoxyethane (0.15 mL, 1.38 mmol) was added and the reaction mixture heated at 60° C. overnight. The mixture was concentrated in vacuo, the residue dissolved in THF (40 mL), EDC (530 mg, 2.76 mmol) added, and the mixture heated at 60° C. for 4 h. The mixture was concentrated in vacuo and the residue purified by chromatography (100 g column, 2M methanolic ammonia/DCM gradient) to give the crude product which was further purified by MDAP (HpH) to give 7-(3,5-dimethylisoxazol-4-yl)-8-methoxy-N-(2-methoxyethyl)-1-((R)-1-(pyridin-2-yl)ethyl)-1H-imidazo[4,5-c]quinolin-2-amine (122 mg, 0.258 mmol, 19% yield) as a white solid. LCMS: (Formate, 2 min), Rt 0.73 mins, MH+ 473.

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