Hydrochloric Acid → 4-((3-Methoxyphenyl)amino)-8-methyl-6-((3-(4-oxopiperidine-1-carbonyl)phenyl)sulfonyl)quinoline-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

HATU (348 mg, 0.915 mmol) and DIEA (0.319 mL, 1.83 mmol) were added to a stirring solution of 3-[[3-carbamoyl-4-[(3-methoxyphenyl)amino]-8-methylquinolin-6-yl]sulfonyl]benzoic acid (300 mg, 0.61 mmol) in DMF (6 mL) at rt. After 5 min. 1,4-dioxa-8-azaspiro[4.5]decane (0.156 mL, 1.22 mmol) was added and the resulting solution was stirred for an additional 1.5 h. The reaction mixture was poured into H2O (50 mL) and filtered. The filter cake was washed with H2O then dried to give a yellow solid. To the solid dissolved in THF (6 mL) was added 5 N HCl (1.22 mL, 6.1 mmol). The reaction mixture was heated to 50° C. and stirred over night. The resulting mixture was cooled to rt, and diluted with EtOAc (20 mL). The organic layer was washed with said. NaHCO3 (20 mL), H2O (20 mL), brine (20 mL), dried over Na2SO4 (s), then concentrated to give the title compound (361 mg) as a yellow solid. The compound was used with no further purification. ES/MS calcd. for C30H29N4O6S+ 573.2. Found m/z=573.2 (M+H)+.

Provenance & Evidence