Sodium hydride → 7-[3-(3-bromo-2-oxo-2H-quinolin-1-yl)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 69059

反応式

HRID 69059 の反応式
[H-].[Na+].[Br:3][C:4]1[C:5](=[O:14])[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.[Br-].[Li+].[CH2:17]([N:19]1[C:25](=[O:26])[C:24]([CH3:28])([CH3:27])[C:23](=[O:29])[N:22]([CH3:30])[C:21]2[CH:31]=[C:32]([O:35][CH2:36][CH2:37][CH2:38]I)[CH:33]=[CH:34][C:20]1=2)[CH3:18]>CN(C=O)C>[Br:3][C:4]1[C:5](=[O:14])[N:6]([CH2:38][CH2:37][CH2:36][O:35][C:32]2[CH:33]=[CH:34][C:20]3[N:19]([CH2:17][CH3:18])[C:25](=[O:26])[C:24]([CH3:28])([CH3:27])[C:23](=[O:29])[N:22]([CH3:30])[C:21]=3[CH:31]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 82050Lithium BromideHCID 2683383-Bromoquinolin-2-olHCID 686727921-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

生成物 1

HCID 669616127-[3-(3-bromo-2-oxo-2H-quinolin-1-yl)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione収率 51.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Under ice cooling, sodium hydride (60% in oil, 0.2 g) was added to a DMF solution (10 ml) of 3-bromo-1H-quinoline-2-one (1.0 g). The mixture was stirred at the same temperature for 15 minutes. Lithium bromide (0.76 g) was added to the mixture, and the liquid was stirred at the same temperature for another 15 minutes, and then at room temperature for an hour. The reaction mixture was cooled to 0° C., and 1-ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (2.1 g) was added thereto. The mixture was stirred at room temperature for 2 hours, and at 50° C. for 8 hours. The reaction mixture was poured to ice water, and the generated insoluble matter was separated. The insoluble matter was dissolved in a mixed solvent of ethyl acetate and dichloromethane. The liquid was dried with sodium sulfate and condensed under reduced pressure. Ethyl acetate was added to the residue. The generated insoluble matter was separated and dried to give the title compound (1.2 g) as a white powder.

後処理

  1. stirringthe liquid was stirred at the same temperature for another 15 minutes
  2. waitat room temperature for an hour
  3. stirringThe mixture was stirred at room temperature for 2 hours
  4. waitat 50° C. for 8 hours
  5. customthe generated insoluble matter was separated
  6. dissolutionThe insoluble matter was dissolved in a mixed solvent of ethyl acetate and dichloromethane
  7. dry with materialThe liquid was dried with sodium sulfate and condensed under reduced pressure
  8. additionEthyl acetate was added to the residue
  9. customThe generated insoluble matter was separated
  10. customdried

出典と根拠

ORDレコード
ord-8fbdbb83ee39465bb6b9668d4159a9fa
出典データセット
uspto-grants-2014_09
特許番号
US08822453B2

関連ノート

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