Water → HCID 18789977, compound

Participants

Reaction Conditions

Reaction Steps

1-[4-Nitro-2-(1H-pyrrol-1-yl)phenoxy]-2-[N-(3,4-dimethoxyphenethyl)-N-isopropylamino]ethane (0.9 g, 1.98 mmol) was dissolved in 50 ml of a 1:1 solvent system of ethyl acetate and methanol; following 10% Pd/C (0.4 g), the solution was stirred at room temperature for 1 h as hydrogen gas was introduced. Thereafter, the reaction solution was filtered through Celite and the solvent was evaporated; the resulting residue (0.7 g) was dissolved in pyridine (20 ml) and, thereafter, the solution was cooled to 0° C. and methanesulfonyl chloride (0.19 ml, 2.5 mmol) was slowly added dropwise and the mixture was stirred at room temperature for 2 h; thereafter, water was added and extraction was conducted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was evaporated; the resulting residue was purified by being subjected to column chromatography on silica gel using a 7:3:1 solvent system of cyclohexane, ethyl acetate and methanol as an eluent. The fractions containing the product were collected and the solvent was evaporated; the residue was dissolved in methanol (10 ml); after cooling to 0° C., a solution of 1N HCl (0.15 ml) saturated with ethyl ether was added and the mixture was stirred for 20 min to effect evaporation and thereby yield the titled compound 1-[4-methanesulfonamido-2-(1H-pyrrol-1-yl)phenoxy]-2-[N-(3,4-dimethoxyphenethyl)-N-isopropylamino]ethane hydrochloride (0.28 g).

Provenance & Evidence