Dimethylformamide → RS-93522

Participants

Reaction Steps

Similarly, a solution of 4.5 g of 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[2-(4-aminophenyl)ethoxycarbonyl]-1,4-dihydropyridine (11), 1.8 ml 2-bromoethanol, 2 ml triethylamine and 20 ml DMF was stirred at 80° C. for 3 h. The mixture was added to water and extracted with ethyl acetate. The ethyl acetate was washed with water, dried over Na2SO4, evaporated to a residue, and purified by silica gel chromatography with 75% ethyl acetate-hexane to afford 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-hydroxyethylamino)phenyl]ethoxycarbonyl)-1,4-dihydropyridine (1) as a free base. This was dissolved in methanolic HCl and evaporated under reduced pressure to yield 2.6 g of 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-hydroxyethylamino)phenyl]ethoxycarbonyl)-1,4-dihydropyridine hydrochloride as an amorphous solid, m.p. 102°-104° C. Calculated for C26H30ClN3O7 : C-58.70, H-5.68, N-7.90. Found: C-58.50, H-5.72, N-7.80.

Provenance & Evidence