反应详情

A solution of 70 mg (0.093 mmole) of 2-[4-amino-2-(trifluoromethyl)phenyl]-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Example 56), 33 mg (0.31 mmole) of benzaldehyde, 2.1 mL of piperidine, and 2.5 mL of isopropanol was stirred at 95° C. overnight. The crude material obtained after cooling and evaporation of volatiles was dissolved in 2.2 mL MeOH, charged with 1.3 mL of a 1M solution of sodium cyanoborohydride in THF (1.3 mmole), and stirred at room temperature for 2 hours. Water (160 mL) was added at 0° C., and the resulting mixture stirred at 0° C. for 2 hours. After evaporation of volatiles, the crude product was flash chromatographed over silica gel (gradient elution with 0.5-5.0% MeOH/CH2Cl2) to afford 27 mg (38%) of the desired product as a cream-colored solid, mp >107° C. (gradual), homogeneous by TLC (9:1MeOH/CH2Cl2), mass spectrum (FAB) m/e 774 (M+1)+.

1. customThe crude material obtained
2. temperatureafter cooling
3. customevaporation of volatiles
4. dissolutionwas dissolved in 2.2 mL MeOH
5. stirringthe resulting mixture stirred at 0° C. for 2 hours
6. customAfter evaporation of volatiles
7. customchromatographed over silica gel (gradient elution with 0.5-5.0% MeOH/CH2Cl2)