三乙胺 → Cyclohexane n-[1,1-dimethyl-2-(3-nitro-7-phenylquinolin-4-ylamino)ethyl]carboxamide

HRID 9408

反应方程式

HRID 9408 反应方程式
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]([CH3:19])([NH2:18])[CH3:17])=[CH:11][CH:10]=[C:9]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:8]=2)([O-:3])=[O:2].C(N(CC)CC)C.[CH:33]1([C:39](Cl)=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>ClCCl>[CH3:17][C:16]([NH:18][CH:39]=[O:40])([CH3:19])[CH2:15][NH:14][C:13]1[C:12]2[C:7](=[CH:8][C:9]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2].[CH2:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

参与物

5

反应物 3

HCID 8471三乙胺HCID 75938环己甲酰氯HCID 86593761N1-(3-nitro-7-phenylquinolin-4-yl)-2-methylpropane-1,2-diamine

产物 1

HCID 87586912Cyclohexane n-[1,1-dimethyl-2-(3-nitro-7-phenylquinolin-4-ylamino)ethyl]carboxamide收率 70%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

A solution of N1-(3-nitro-7-phenylquinolin-4-yl)-2-methylpropane-1,2-diamine (3.56 g, 10.6 mmol) in dichloromethane (100 mL) was cooled to 0° C. Triethylamine (3.0 mL, 21 mmol) and cyclohexanecarbonyl chloride (1.55 mL, 11.6 mmol) were sequentially added. The reaction was allowed to warm to ambient temperature and stirred for two hours. The reaction was washed sequentially with water (2×100 mL) and brine (100 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 65:35 hexanes:ethyl acetate) to provide 3.33 g of cyclohexane N-[1,1-dimethyl-2-(3-nitro-7-phenylquinolin-4-ylamino)ethyl]carboxamide as a yellow solid.

后处理

  1. washThe reaction was washed sequentially with water (2×100 mL) and brine (100 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel (eluting with 65:35 hexanes:ethyl acetate)

来源与证据

ORD记录
ord-f15ea28ffbee4c82a8f9b5a3dcec7661
来源数据集
uspto-grants-2006_08
专利号
US07091214B2

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