Ammonium Chloride → HCID 66681377, compound

Participants

Reaction Steps

5-(3-{[5-(Azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-[(1S)-2-methoxy-1-methylethoxy]phenyl)-1H-pyrrole-2-carboxylic acid (800 mg, 1.65 mmol) synthesized in Example (71a) was dissolved in dichloromethane (10.0 mL), and 2-chloroethylamine hydrochloride (300 mg, 2.59 mmol), WSCI•HCl (630 mg, 3.29 mmol) and 4-dimethylaminopyridine (400 mg, 3.27 mmol) were added, followed by stirring at room temperature under nitrogen atmosphere for 2.5 days. To the reaction solution, a saturated aqueous ammonium chloride solution (30 mL) was added, and extraction was carried out with dichloromethane (30 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate) to afford the desired compound (210 mg, yield 23%) as a white solid.

Provenance & Evidence