反应 #1583831

反应方程式

water

methyl N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate

5-chloro-3-(1-methylethyl)-1,2,4-thiadiazole

product

5-chloro-3-(1-methylethyl)-1,2,4-thiadiazole

potassium carbonate

→

title compound

methyl N-[[2-chloro-5-[1-[3-(1-methylethyl)-1,2,4-thiadiazol-5-yl]-1H-pyrazol-3-yl]phenyl]methyl]carbamate

溶剂

N-methyl-2-pyrrolidinone

反应条件

后处理

1. 1
   萃取the aqueous mixture was extracted with ethyl acetate (2×50 mL)
2. 2
   洗涤The combined organic extracts were washed with water
3. 3
   干燥dried over magnesium sulfate
4. 4
   过滤filtered
5. 5
   浓缩concentrated under reduced pressure
6. 6
   其他The resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant)

实验过程

A mixture of methyl N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate (i.e. the product of Step B, Example 4) (0.02 g, 0.75 mmol), 5-chloro-3-(1-methylethyl)-1,2,4-thiadiazole (i.e. the product of Step A) (0.61 g, 3.75 mmol) and potassium carbonate (0.25 g, 1.5 mmol) in N-methyl-2-pyrrolidinone (2.5 mL) was heated in a Biotage Creator XM microwave apparatus at 165° C. for 15 minutes. The reaction mixture was poured into water (60 mL), and the aqueous mixture was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant) to provide the title compound, a compound of the present invention, as a solid (0.5 g).

来源