Acetic Acid → 1-Methyl-1H-imidazole-4-sulfonic acid {2-[8-(3,4-dichloro-benzyl)-7-ethylamino-5,6,7,8-tetrahydro-naphthalen-2-yloxy]-ethyl}-amide

Participants

Reaction Steps

Ethyl 1-(3,4-dichlorobenzyl)-7-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (example 3, 60.0 mg, 0.103 mmol) was dissolved in dichloromethane (5 ml) and acetaldehyde (5.45 mg, 0.124 mmol μl) and molsieve 3 {acute over (Å)} were added and the mixture was stirred for 3 h. Acetic acid (7.07 mg, 0.118 mmol) was added and the mixture was stirred for another 3 h. MeOH (5 ml) and sodium cyanoborohydride (14.8 mg, 0.236 mmol) were added and it was stirred for another 14 h. Water was added and it was extracted with dichloromethane. The organic layer was washed with saturated NaHCO3 solution, washed and evaporated. The residue was purified by column chromatography using SiO2 and CH2Cl2/MeOH 95:5→90:10. The product was precipitated as an HCl salt from 6N HCl in isopropanol and isopropylether to obtain the product as a white salt (17 mg, 25%).

Provenance & Evidence