Pyridine → HCID 58902258, compound

Participants

Reaction Steps

A solution of N-(3-tert-butylphenyl)-7-[(2-isocyanatopyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxamide (250 mg, 0.56 mmol), [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol (150 mg, 1.13 mmol) and pyridine (0.091 mL, 1.13 mmol) in THF (10 mL) was allowed to stir at rt. After 2 h, additional pyridine (0.14 mL) and [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol (0.220 mg) were added. The reaction mixture was heated at 70° C. overnight and then another portion of pyridine (0.10 mL) and [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol (0.150 mg g) were added. Heating continued for an additional 2 h and then the reaction mixture was subjected to MWI at 135° C. for 5 min. The reaction mixture was diluted with EtOAc and washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl {4-[(7-{[(3-tert-butylphenyl)amino]carbonyl}-5,6,7,8-tetrahydronaphthalen-2-yl)-oxy]pyridin-2-yl}carbamate (290 mg, 89%) as a white solid. LCMS: (FA) ES+574.4.

Provenance & Evidence