반응 #1583831

반응 방정식

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

용매

N-methyl-2-pyrrolidinone

반응 조건

후처리

1. 1
   추출the aqueous mixture was extracted with ethyl acetate (2×50 mL)
2. 2
   세척The combined organic extracts were washed with water
3. 3
   건조dried over magnesium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant)

실험 절차

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).

출처