1-(2-氨乙基)吡咯烷 → HCID 86732796，化合物

HRID 525928笔记

反应方程式

HRID 525928 反应方程式
[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:37])[C:5]([C:34](O)=[O:35])=[N:6][N:7]2[CH2:32][CH3:33].C(N(CC)CC)C.ClC(OCC(C)C)=O.[N:53]1([CH2:58][CH2:59][NH2:60])[CH2:57][CH2:56][CH2:55][CH2:54]1>O1CCCC1>[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:37])[C:5]([C:34]([NH:60][CH2:59][CH2:58][N:53]1[CH2:57][CH2:56][CH2:55][CH2:54]1)=[O:35])=[N:6][N:7]2[CH2:32][CH3:33]

参与物

6

反应物 4

HCID 13441-(2-氨乙基)吡咯烷HCID 8471三乙胺HCID 62365氯甲酸异丁酯HCID 86732795HCID 86732795，化合物

产物 1

HCID 86732796HCID 86732796，化合物收率 33.8%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

反应条件

温度
0 °C

实验过程

To a suspension of 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylic acid (3 g, 5.71 mmol) in tetrahydrofuran (THF) (25 mL) was added triethylamine (0.876 mL, 6.29 mmol), followed by isobutyl chloroformate (0.826 mL, 6.29 mmol). The reaction mixture was stirred at 0° C. for 30 min. 2-(Pyrrolidin-1-yl)ethanamine (0.979 g, 8.57 mmol) was added and the mixture was stirred at 0° C. for 30 min and warmed up to room temperature for 2 h. Solvent was removed and the residue was chromatographed to afford 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-1,4-dihydrocinnoline-3-carboxamide (1.2 g, 1.932 mmol, 33.8% yield). LCMS: (M+H)+: 621.2

后处理

  1. stirringthe mixture was stirred at 0° C. for 30 min
  2. temperaturewarmed up to room temperature for 2 h
  3. customSolvent was removed
  4. customthe residue was chromatographed

来源与证据

ORD记录
ord-a604e812734c430f9815b2988f7e8052
来源数据集
uspto-grants-2016_05
专利号
US09340556B2

反应笔记

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