hydroxylamine-O-sulfonic acid → HCID 44482191, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[4-(1-{[1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-4-carbonyl]-amino}-butyl)-pyridine-2-sulfonyl]-propionic acid methyl ester (60 mg, 0.12 mmol) in anhydrous DMSO (1.5 mL) is added sodium methoxide in methanol (2.7 M solution freshly prepared by dissolving 250 mg of sodium in 4.0 mL of methanol, 44 μL, 0.12 mmol). After stiffing at room temperature for 15 min, the reaction mixture is cooled to 0° C. and treated with a solution of hydroxylamine-O-sulfonic acid (260 mg, 2.3 mmol) and sodium acetate (150 mg, 1.9 mmol) in water (6 mL). The resultant mixture is warmed to room temperature and stirred overnight for 18 hours. EtOAc (100 mL) is added and the phases are separated. The organic layer is washed with water (4×15 mL, until pH of water layer is ˜5), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by preparative reverse phase HPLC (eluted with 10 to 65% CH3CN/H2O and 0.1% TFA as additive) to afford 1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid [1-(2-sulfamoyl-pyridin-4-yl)-butyl]-amide (39 mg, 75%).

Provenance & Evidence