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

HRID 69057ノート

反応式

HRID 69057 の反応式
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+].[CH2:21]([N:23]1[C:29](=[O:30])[C:28]([CH3:32])([CH3:31])[C:27](=[O:33])[N:26]([CH3:34])[C:25]2[CH:35]=[C:36]([O:39][CH2:40][CH2:41][CH2:42]I)[CH:37]=[CH:38][C:24]1=2)[CH3:22]>CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:42][CH2:41][CH2:40][O:39][C:36]2[CH:37]=[CH:38][C:24]3[N:23]([CH2:21][CH3:22])[C:29](=[O:30])[C:28]([CH3:32])([CH3:31])[C:27](=[O:33])[N:26]([CH3:34])[C:25]=3[CH:35]=2)[C:4](=[O:12])[C:3]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 27848104-Chloro-3-phenyl-1H-quinoline-2-oneHCID 686727921-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

生成物 1

HCID 706565117-[3-(4-chloro-2-oxo-3-phenyl-2H-quinoline-1-yl)propoxy]-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione収率 42.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-Chloro-3-phenyl-1H-quinoline-2-one (0.3 g) was suspended in DMF (6 ml). Sodium hydride (60% in oil) (51 mg) was added, and the mixture was stirred for 15 minutes at room temperature. 1-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (0.55 g) was added thereto and the mixture was stirred at room temperature for 7 days. The reaction mixture was poured to ice water (50 ml), and the generated insoluble matter was separated. The insoluble matter was dissolved in ethyl acetate. The liquid was dried over sodium sulfate and condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:3). The purified product was condensed under reduced pressure, and the residue was recrystallized from ether, thereby obtaining the title compound (0.28 g) as a white powder.

後処理

  1. stirringthe mixture was stirred at room temperature for 7 days
  2. customthe generated insoluble matter was separated
  3. dissolutionThe insoluble matter was dissolved in ethyl acetate
  4. dry with materialThe liquid was dried over sodium sulfate and condensed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:3)
  6. customcondensed under reduced pressure
  7. customthe residue was recrystallized from ether

出典と根拠

ORDレコード
ord-eddda42932b94501a13323774f1500a5
出典データセット
uspto-grants-2014_09
特許番号
US08822453B2

反応ノート

読み込み中…