تفاعل #51132
ord-a0d0a57b98aa4ae98b108254648bbe0c
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1أخرىsolvent removed by evaporation under diminished pressure
- 2workup.DISSOLUTIONThe residue was redissolved in anhydrous toluene (2 mL)
- 3درجة الحرارةThe mixture was refluxed for 18 h
- 4درجة الحرارةThe reaction was cooled to room temperature
- 5ترشيحthe cream-colored precipitate was filtered
- 6غسيلwashed
- 7أخرىto give 300 mg of crude product as the HCl salt
- 8غسيلthe aqueous layer was washed with two additional portions of methylene chloride
- 9أخرىevaporated
- 10أخرىthe residue was chromatographed by flash silica gel chromatography
- 11غسيلElution
- 12أخرىevaporated
الإجراء التجريبي
Methyl amide 10-5 (220 mg, 0.77 mmol) was dissolved in anhydrous methylene chloride (2 mL) and treated with oxalyl chloride (2M in methylene chloride, 0.77 mL, 1.54 mmol) and DMF (2 drops). The solution was stirred at room temperature for 1 h, then solvent removed by evaporation under diminished pressure. The residue was redissolved in anhydrous toluene (2 mL) and treated with 5[2-(trifluoromethyl)phenyl]1H-tetrazole (214 mg, 1 mmol). The mixture was refluxed for 18 h. The reaction was cooled to room temperature and the cream-colored precipitate was filtered and washed to give 300 mg of crude product as the HCl salt. The salt was taken up in methylene chloride/1N HCl and the aqueous layer was washed with two additional portions of methylene chloride. The organic layers were combined and evaporated and the residue was chromatographed by flash silica gel chromatography. Elution was carried out with a gradient ranging from 0 to 5% methanol/methylene chloride. The appropriate fractions were combined and evaporated to give 3-{4-[2-(ethylsulfonyl)ethyl]bicyclo[2.2.2]oct-1-yl}-4-methyl-5-[2-(trifluoromethyl)phenyl]-4H -1,2,4-triazole (10-6) as a white powder.