反応 #71432

反応方程式

H2O

Trimethyl aluminum

8-(3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl ester

5-(4-ethyl-piperazin-1-ylmethyl)-pyridin-2-ylamine

→

title compound

収率 35.1%

8-(3,5-Dimethoxy-phenyl)-quinoxaline-5-carboxylic acid [5-(4-ethyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amide

収率 35.1%

溶媒

toluene

反応条件

後処理

1. 1
   温度heated
2. 2
   温度to reflux
3. 3
   workup.STIRRINGstirred for 3 h
4. 4
   温度to cool
5. 5
   ろ過filtered through a pad of celite
6. 6
   抽出The filtrate was extracted with EtOAc
7. 7
   洗浄The organic phase was washed with H2O and brine
8. 8
   乾燥dried (Na2SO4)
9. 9
   ろ過filtered
10. 10
    濃縮concentrated
11. 11
    その他The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1)

実験手順

Trimethyl aluminum (2 M in toluene, 0.37 mL, 0.74 mmol, 2.5 equiv) was added to a mixture of 8-(3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl ester (Step 115.1) (100 mg, 0.30 mmol) and 5-(4-ethyl-piperazin-1-ylmethyl)-pyridin-2-ylamine (Step 26.1; purified by column chromatography) (78 mg, 0.36 mmol, 1.2 equiv) in toluene (2 mL). The reaction mixture was stirred for 1 h at rt, heated to reflux, stirred for 3 h, allowed to cool, poured onto EtOAc and H2O, and filtered through a pad of celite. The filtrate was extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1) followed by reverse-phase preparative HPLC to afford 54 mg of the title compound as a pale yellow solid. Title compound: ESI-MS: 513.2 [M+H]+; tR=3.54 min (System 1); TLC: Rf=0.29 (DCM/MeOH/NH3aq, 94:5:1).

出典