Reacción #1583831

Ecuación de reacción

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

Disolventes

N-methyl-2-pyrrolidinone

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente