Triethylamine → 6-(phenylsulfonamido)-N-(tetrahydro-2H-pyran-2-yloxy)quinoline-3-carboxamide

Participants

Reaction Steps

6-[(Phenylsulfonyl)amino]quinoline-3-carboxylic acid (0.11 g, 0.335 mmol) was dissolved in N,N-dimethylformamide (2.5 mL) and triethylamine (0.14 mL, 1 mmol) was added. Tetramethylfluoroformamidinium hexafluorophosphate (0.106 g, 0.402 mmol) was added and the reaction mixture was allowed to stir at room temperature for 15 min. Then O-(tetrahydropyran-2-yl)hydroxylamine (0.0471 g, 0.402 mmol) was added and the reaction was stirred at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate three times. The combined extracts were washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (0-10% MeOH in methylene chloride gradient with 0.1% formic acid) to afford the product (Int-13, 0.027 g, 18%). LC-MS: (AA) ES+ 428.

Provenance & Evidence