Dimethylformamide → N-[6-(4-Hydroxycyclohex-1-en-1-yl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)-pyridin-2-yl]-1H-pyrazole-4-carboxamide

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Reaction Steps

Oxalyl chloride (0.20 ml) and N,N-dimethylformamide (catalytic amounts) were added at room temperature to a solution of 5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid (175 mg) described in Reference Example 8 in dichloromethane (10 ml) and stirred at room temperature for two hours. The solvent and an excess amount of oxalyl chloride were evaporated, and toluene (10 ml) was added to the resulted reaction mixture. Next, a solution of 4-(5-amino-3-methylpyridin-2-yl)cyclohex-3-en-1-ol (120 mg) described in Reference Example 111 in pyridine (10 ml) was added under ice-cooling, and the mixture was 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, the resulting solid was filtered and dried at 60° C. in vacuo to give the titled compound (146 mg) as a white solid.

Provenance & Evidence