반응 #45171

반응 방정식

1-ethyl-1,4-diazepane

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

→

title compound

수율 59.4%

N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-5-(4-ethyl-1,4-diazepan-1-yl)pyrazine-2-carboxamide

수율 59.4%

용매

MeOH

DMSO

반응 조건

후처리

1. 1
   온도was increased to 60° C.
2. 2
   workup.STIRRINGthe reaction mixture was stirred for a further 15 mins
3. 3
   기타the crude product was purified by ion exchange chromatography
4. 4
   세척The desired product was eluted from the column
5. 5
   기타were evaporated to dryness
6. 6
   기타to afford crude product as an orange dry film
7. 7
   기타The crude product was purified by preparative HPLC
8. 8
   workup.ADDITIONFractions containing the desired compound
9. 9
   기타were evaporated to dryness

실험 절차

1-ethyl-1,4-diazepane (205 mg, 1.60 mmol) was added to 5-chloro-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]pyrazine-2-carboxamide (310 mg, 0.80 mmol) in DMSO (4.00 ml) at 25° C. The resulting solution was stirred at room temperature for 2 h. The reaction was incomplete so the temperature was increased to 60° C. and the reaction mixture was stirred for a further 15 mins. The reaction mixture was diluted with MeOH (5 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 crude product as an orange dry film. 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 (228 mg, 59%) as a white solid.

출처