Реакция #1583831

Уравнение реакции

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

Растворители

N-methyl-2-pyrrolidinone

Условия реакции

Обработка

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

Методика

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).

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