反应详情

165 mg (75% by weight; 0.384 mmol) of 3-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-4-(trifluormethyl)benzoic acid and 68.9 mg (0.614 mmol) of 5-hydroxy-1,3-dimethylpyrazole were initially charged in 20 ml of dichlormethane, and 128 mg (0.666 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added. The mixture was stirred at RT for 16 h and, for work-up, washed with 1 M hydrochloric acid. After phase separation, the organic phase was dried, filtered and freed from the solvent on a rotary evaporator. The residue was purified chromatographically and the intermediate obtained was then dissolved in 15 ml of acetonitrile. 104 mg (1.02 mmol) of triethylamine, eight drops of trimethylcyanide and a spatula tip of potassium cyanide were then added. The mixture was stirred at RT for 16 h and, for work-up, freed from the solvent. The residue was taken up in dichloromethane and washed with 3 ml of 1M hydrochloric acid. After phase separation, the organic phase was freed from the solvent and the residue was purified chromatographically, which gave 31.3 mg of 5-hydroxy-1,3-dimethyl-4-[3-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-4-(trifluoromethyl)benzoyl]pyrazole in a purity of 85% by weight.

1. washwashed with 1 M hydrochloric acid
2. customAfter phase separation
3. customthe organic phase was dried
4. filtrationfiltered
5. customfreed from the solvent on a rotary evaporator
6. customThe residue was purified chromatographically
7. customthe intermediate obtained
8. stirringThe mixture was stirred at RT for 16 h and, for work-up
9. washwashed with 3 ml of 1M hydrochloric acid
10. customAfter phase separation
11. customthe residue was purified chromatographically