Methyl iodide → HCID 86754431, compound

Participants

Reaction Steps

Part A. N-[3-(cyano)phenyl]-N-[2-[2'-(1,1-dimethylethylaminosulfonyl)[1,1'-biphenyl]-4-yl]propyl]-N-2-(hydroxy)ethylamine (1.00 gm, 2.89 mmol) was dissolved in 100 mL of anhydrous THF followed by the addition of NaH (60% dispersion in mineral oil, 0.23 gm, 5.78 mmol). Once the evolution of gas ceased, iodomethane was added (0.411, 0.18 mL, 2.89 mmol) and the solution was allowed to stir overnight at room temperature. The solution was quenched with dilute HCl, and the volatiles removed in vacuum. N-[3-(Cyano)phenyl]-N-[2-[2'-(1,1-dimethylethylaminosulfonyl)[1,1'-biphenyl]-4-yl]propyl]-N-2-(methoxy)ethylamine was isolated after HPLC purification on Vydac C-18 column eluting with solvent A (acetonitrile:water:TFA 80:20:0.2) and solvent B (water:TFA 99.8:0.2) used as a gradient, as a clear oil (0.100 gm, 7%). MS m/e 506.4 (M+H)+.

Provenance & Evidence