1-Methylpiperazine → HCID 178427945, compound

Participants

Reaction Steps

Crude 6-chloro-2-(4-fluoro-3-nitrophenyl)-7-methyl-3H-imidazo[4,5-b]pyridine (Example 252) (333 mg) and 1-methylpiperazine (1.0 ml) were mixed and left at room temperature for 15 min, whereupon it was diluted with EtOAc (50 ml) and washed with water (100 ml). The aqueous phase was extracted with EtOAc (50 ml) and the combined organic phase was evaporated in vacuo. The yellow oily residue was dissolved in methanol (100 ml) and hydrogenated in a Parr apparatus (Raney nickel, 60 psi, 5 h). The catalyst was removed by filtration and the solvent removed in vacuo. The residue was purified by semi-preparative HPLC-C18 affording the product as a trifluoroacetate. The salt was dissolved in EtOAc (10 ml) and washed with aqueous 10% NaHCO3 solution (5 ml), brine (5 ml) and dried (MgSO4). Evaporation of the solvent yielded the product as an off-white powder (67 mg, 25%).

Provenance & Evidence