三乙胺 → 4-(methylamino)-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide

HRID 339564

反应方程式

HRID 339564 反应方程式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.ON1C2C=CC=CC=2N=N1.[CH3:28][NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1.C(N(CC)CC)C>CN(C=O)C>[CH3:28][NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:15][C:14]2[CH:16]=[CH:17][C:11]([C:9]3[N:10]=[C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]4[CH:8]=3)=[CH:12][CH:13]=2)=[O:35])=[CH:32][CH:31]=1

参与物

6

反应物 4

HCID 8471三乙胺HCID 663454-甲氨基苯甲酸HCID 757711-羟基苯并三唑(HOBT)HCID 8210844-(6-Methylimidazo[1,2-a]pyridin-2-yl)aniline

产物 1

HCID 583420774-(methylamino)-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide收率 33.2%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

To a stirred solution of 4-(6-methylimidazo[1,2-a]pyridin-2-yl)aniline (0.10 g, 0.448 mmol), 1-hydroxybenzotriazole (0.06 g, 0.448 mmol), 4-methylaminobenzoic acid (0.068 g, 0.448 mmol) and triethylamine (62 μl, 0.045 g, 0.448 mmol) in dry DMF (5 ml) at 0° C. was added 1-ethyl-3-[3-(dimethylaminopropyl]-carbodiimide hydrochloride (0.086 g, 0.448 mmol) under an atmosphere or argon. After 10 min the cooling bath was removed and the reaction mixture was stirred at room temperature for 4 d. The reaction mixture was then added to water (150 ml) with stirring and the precipitate was collected by filtration. Purification by flash chromatography (25:1 DCM/MeOH) gave the title compound (0.053 g, 33%) as an almost colourless solid.

后处理

  1. customAfter 10 min the cooling bath was removed
  2. additionThe reaction mixture was then added to water (150 ml)
  3. stirringwith stirring
  4. filtrationthe precipitate was collected by filtration
  5. customPurification by flash chromatography (25:1 DCM/MeOH)

来源与证据

ORD记录
ord-7e9a0e0620404989977747eea8dccf69
来源数据集
uspto-grants-2014_11
专利号
US08895313B2

关联笔记

加载中…