Dimethylformamide → HCID 86692583, compound

Participants

Reaction Steps

Oxalyl chloride (0.25 ml) and N,N-dimethylformamide (catalytic amounts) were added at room temperature to a solution of 1-(4-tert-butylphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid (222 mg) described in Reference Example 17 in dichloromethane (5 ml) and stirred at room temperature for two hours. The solvent and an excess amount of oxalyl chloride were evaporated. Toluene (5 ml) was added to the resulting reaction mixture, a solution of 6-(1,4-dioxaspiro[4.5]decan-8-yl)pyridine-3-amine (185 mg) described in Reference Example 102 in pyridine (4 ml) was added under ice-cooling, and stirred at room temperature overnight. After the reaction, 1N aqueous solution of sodium hydroxide was added under ice-cooling and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated. The resulting residue was purified with a silica gel column chromatography (n-hexane/ethyl acetate) and ethanol was added to give 1-(4-tert-butylphenyl)-N-[6-(1,4-dioxaspiro[4.5]decan-8-yl)pyridin-3-yl]-5-methyl-1H-pyrazole-4-carboxamide (242 mg) as a white solid.

Provenance & Evidence