反应 #324420

反应方程式

3-benzyl-5-(4-methoxyphenyl)pyrazin-2-amine

water

KBr

m-anisoyl chloride

→

N-[3-Benzyl-5-(4-methoxyphenyl)pyrazin-2-yl]-3-methoxybenzamide

溶剂

pyridine

dichloromethane ethyl acetate

反应条件

后处理

1. 1
   其他at room temperature
2. 2
   温度the mixture was heated
3. 3
   温度After cooling to room temperature, to the mixture
4. 4
   萃取the product was extracted with dichloromethane (×3)
5. 5
   萃取The combined organic extract
6. 6
   干燥was dried over anhydrous sodium sulfate
7. 7
   过滤After filtration and concentration under reduced pressure
8. 8
   其他the residual pyridine was azeotropically removed with toluene (×3)
9. 9
   其他The residue was purified by column chromatography (silica gel 100 g, dichloromethane/ethyl acetate=9/1)
10. 10
    其他The residue was recrystallized from ethyl acetate
11. 11
    其他to give Compound fly (967 mg, 2.27 mmol, 82.5%) as a colorless solid

实验过程

To a solution of 3-benzyl-5-(4-methoxyphenyl)pyrazin-2-amine (12) (synthesized by the process of M. Adamczyk, et al., Org. Prep. Proced. Int., 33, 477-485 (2001)) (800 mg, 2.75 mmol) in pyridine (10 mL) were successively added 4-(dimethylamino)pyridine (33.6 mg, 275 μmol) and m-anisoyl chloride (18) (773 μL, 5.50 mmol) at room temperature, and the mixture was heated with stirring at 50° C. for 22 hours. After cooling to room temperature, to the mixture was added water and the product was extracted with dichloromethane (×3). The combined organic extract was dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the residual pyridine was azeotropically removed with toluene (×3). The residue was purified by column chromatography (silica gel 100 g, dichloromethane/ethyl acetate=9/1). The residue was recrystallized from ethyl acetate to give Compound fly (967 mg, 2.27 mmol, 82.5%) as a colorless solid. Rf=0.63 (dichloromethane/ethyl acetate=9/1); 1H NMR (400 MHz, DMSO-d6) δ 3.83 (s, 6H), 4.19 (s, 2H), 7.05-7.12 (AA′BB′, 2H), 7.14-7.28 (m, 6H), 7.42-7.49 (m, 2H), 7.53 (d, 1H, J=7.5 Hz), 8.06-8.12 (AA′BB′, 2H), 8.98 (s, 1H), 10.77 (s, 1H); 13C NMR (67.8 MHz, CDCl3) δ 41.5, 55.3, 55.4, 112.5, 114.3 (2C), 118.6, 119.3, 126.7 (2C), 128.1, 128.55, 128.61 (2C), 128.5 (2C), 129.6, 135.0, 136.8, 137.7, 143.3, 149.2, 149.9, 159.8, 160.9, 165.7; IR (KBr, cm−1) 700, 746, 833, 1022, 1040, 1117, 1179, 1254, 1300, 1325, 1373, 1416, 1441, 1501, 1607, 1655, 2936, 3265; Anal. Calcd. For C26H23N3O3: C, 73.39; H, 5.45; N, 9.88. Found: C, 73.55; H, 5.36; N, 9.86.

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