反応 #44593

反応方程式

triethylamine

2-(3,4,5-trimethoxyphenylamino)-6-(4-aminophenyloxy)-pyrazine

4-fluorophenylcarbonyl chloride

→

title compound

収率 50.0%

2-(3,4,5-Trimethoxyphenylamino)-6-[4-(4-fluorophenylcarbonyl)-aminophenyl]-pyrazine

収率 50.0%

溶媒

dioxane

反応条件

後処理

1. 1
   その他The reaction mixture was evaporated to dryness
2. 2
   workup.DISSOLUTIONredissolved in 10 mL AcOEt
3. 3
   洗浄the solution washed (2×10 mL brine)
4. 4
   その他dried
5. 5
   その他purified by column chromatography (AcOEt)

実験手順

Method LL. In a tube suitable for parallel synthesis, 2-(3,4,5-trimethoxyphenylamino)-6-(4-aminophenyloxy)-pyrazine (50 mg, 0.14 mmol) and 4-fluorophenylcarbonyl chloride (21 μL, 0.17 mmol) were stirred under nitrogen for 20 hours in dry dioxane (5 mL) in the presence of triethylamine (25 mL, 1.2 eq). The reaction mixture was evaporated to dryness, redissolved in 10 mL AcOEt, the solution washed (2×10 mL brine), dried, and purified by column chromatography (AcOEt) to give the title compound (33 mg). Yield: 50%. 1H NMR (250 MHz, DMSO-d6) δ 3.69 (s, 3H, [CH3O]4), 3.89 (s, 6H, [CH3O]3+5), 7.32 (s, 2H, Harom2′+6′), 7.44 (t, 2H, Harom 2″+6″, J=8.8 Hz), 7.98 (d, 2H, Harom 3+5, J=8.6 Hz), 8.10-8.21 (m, 4H, Harom 3″+5″ and Harom 2+6), 8.18 (s, 1H, HPz 5), 8.57 (s, 1H, HPz 3), 9.61 (s, 1H, NH), 10.50 (s, 1H, NHamide). m/z 475.2 [(M+H)+ calcd for C26H23FN4O4 474.2].

出典