Pyridine → 2,6-dichloro-3-[[[1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl]amino]-N-(1-methylethyl)-4-pyridinecarboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 268 mg (0.92 mmol) of 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (from Step F) in 5 mL of dichloromethane was added 160 μL (1.84 mmol) of oxalyl chloride and two drops of DMF in sequence at room temperature. The mixture was then stirred at the same temperature for 1 hour. The crude mixture was then concentrated in vacuo. The resulting mixture was dissolved with 5 mL of acetonitrile followed by additions of 280 mg (0.92 mmol) of the compound prepared in Step D and 298 μL (3.68 mmol) of pyridine in sequence. The reaction mixture was warmed to 70° C. for 2 hours and allowed to cool to room temperature. A solution of 157 μL (1.84 mmol) of isopropylamine in 1 mL of acetonitrile was added to the mixture and it was warmed to 60° C. for 1 hour. The reaction was allowed to cool to room temperature and quenched with water. The aqueous layer was extracted with ethyl acetate and the organic layer was dried with MgSO4 and concentrated in vacuo. The resulting mixture was purified with a silica gel column to give 250 mg of the title compound, a compound of the invention, as a white solid (52%). m.p. 240-242° C.

Provenance & Evidence