Dimethylformamide → HCID 56961708, compound

Participants

Reaction Steps

Oxalyl chloride (0.14 ml) and N,N-dimethylformamide (catalytic amounts) were added at room temperature to a solution of 1-(3-fluoro-5-trifluoromethylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid (120 mg) described in Reference Example 130 in dichloromethane (5 ml) and stirred at room temperature for two hours. The solvent and an excess amount of oxalyl chloride were evaporated, and toluene (5 ml) was added to the resulted reaction mixture. Next, a solution of 2-(4-hydroxycyclohex-1-en-1-yl)-3-methyl-5-aminopyridine (81 mg) described in Reference Example 111 in pyridine (5 ml) was added thereto and stirred at room temperature overnight. After the reaction, 1N aqueous solution of sodium hydroxide was added under ice-cooling and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with a silica gel column chromatography (chloroform/methanol), washed with ethanol and the resulting solid was collected by filtration and dried at 60° C. in vacuo to give the titled compound (107 mg) as a white solid.

Provenance & Evidence