Reacción #45146

Ecuación de reacción

N,N-dimethylpyrrolidin-3-amine

5-chloro-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]pyrazine-2-carboxamide

→

title compound

Rendimiento 80.0%

N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-5-(3-dimethylaminopyrrolidin-1-yl)pyrazine-2-carboxamide

Rendimiento 80.0%

Disolventes

methanol

dimethylsulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe crude product was purified by ion exchange chromatography
2. 2
   LavadoThe desired product was eluted from the column
3. 3
   Otrowere evaporated to dryness
4. 4
   Otroto afford impure product as a brown oil
5. 5
   OtroThe crude product was purified by preparative HPLC
6. 6
   workup.ADDITIONFractions containing the desired compound
7. 7
   Otrowere evaporated to dryness

Procedimiento

N,N-dimethylpyrrolidin-3-amine (114 mg, 1.00 mmol) was added to 5-chloro-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]pyrazine-2-carboxamide (136 mg, 0.35 mmol) in anhydrous dimethylsulfoxide (1.75 ml) at 25° C. The resulting solution was stirred at room temperature for 20 mins. The reaction mixture was diluted with methanol (5.00 ml) and the crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford impure product as a brown oil. The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (130 mg, 80%) as a white solid.

Fuente