Potassium Iodide → HCID 13769740, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.62 parts of 5-chloro-1-methyl-4-nitro-1H-imidazole, 3.67 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-3-[(4-fluorophenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-amine, 1.1 parts of sodium carbonate, 0.1 parts of potassium iodide and 90 parts of N,N-dimethylformamide was stirred and heated overnight at 70° C. The reaction mixture was cooled and poured onto water. The product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 2.2 parts (45%) of 3-[(4-fluorophenyl)methyl]-N-[1-[2-[(1-methyl-4-nitro-1H-imidazol-5-yl)amino]ethyl]-4-piperidinyl]-3H-imidazo[4,5-b]pyridin-2-amine; mp. 198.7° C. (compound 11 ).

Provenance & Evidence