Ethanolamine → HCID 66571222, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1-[(1R)-1-phenylethyl]-1H-imidazo[4,5-c]quinoline (for a preparation see Intermediate 12) (30 mg, 0.035 mmol) was dissolved in NMP (0.5 ml), ethanolamine (30 mg) was added and the mixture was heated at 150° C. for 30 min, then cooled, added to water (10 ml) and extracted with EtOAc (10 ml). The organic phase was washed with water (2×10 ml), dried and evaporated. The residue was dissolved in DCM (2 ml), loaded onto a 10 g silica column and eluted with 2M methanolic ammonia/DCM (0-10%). The product-containing fractions were evaporated in vacuo to give 2-({7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1-[(1R)-1-phenylethyl]-1H-imidazo[4,5-c]quinolin-2-yl}amino)ethanol (8.4 mg, 0.018 mmol, 53.0% yield) as a light brown glass. LCMS (formate) Rt 0.77 min, MH+ 458

Provenance & Evidence