Chloride → HCID 136237265, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of hydroxylammoium chloride (0.2 g, 2.88 mmol), sodium hydrogen carbonate (0.3 g, 3.57 mmol) and dimethyl sulfoxide (2 mL) was stirred at 40° C. for 30 min. (S)-1-((2′-cyano-[1,1′-biphenyl]-4-yl)methyl)-N-(1-(3-isopropylphenyl)ethyl)-2,3-dimethyl-1H-indole-5-carboxamide (0.1 g, 0.19 mmol) was added, and the mixture was stirred at 90° C. for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with water and then with brine, and dried over anhydrous sodium sulfate. Thvent was evaporated under reduced pressure, and the residue was dissolved in THF (3 mL), N,N′-carbonyldiimidazole (0.055 g, 0.29 mmol) and then 1,8-diazabicyclo[5,4,0]undec-7-ene (0.05 mL, 0.29 mmol) were added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous potassium hydrogensulfate solution and then with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by preparative-HPLC to obtain the title compound. ESI-MS (m/z): 585 [M+H]+.

Provenance & Evidence