Dichloromethane → HCID 11179417, compound

Participants

Reaction Steps

The 1-(3-carboxymethoxybenzoyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid ethyl ester (119 mg, 0.23 mmol) was suspended in 8 ml of methylene chloride containing 10 equivalent of N-methylpiperizine, 1.1 equivalent of HBTU and 4.0 equivalent of triethylamine. The mixture was stirred at room temperature overnight and then evaporated to remove solvents. The residue was extracted with ethyl acetate and water. The organic layer was dried and solvents were evaporated. The residue was dissolved in 4 ml of methanol and aqueous lithium hydroxide was added (0.5N, 1 ml). The mixture was stirred overnight until all starting material disappeared. The reaction was loaded on a preparative HPLC for purification to give 6,7-Dimethoxy-1-{3-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethoxy]-benzoyl}-isoquinoline-4-carboxylic acid as a fluffy solid (39 mg, 35%). ES-MS calcd for C26H27N3O7 (m/e) 493.5, obsd 494.4 (M+H).

Provenance & Evidence