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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(1-{2-[(2,5-Dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-5-methyl-1H-indole-2-carboxamide

HRID 1376155
ノート
印刷プレビュー

反応式

HRID 1376155 の反応式
O[N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[CH3:9]CN=C=NCCCN(C)C.[C:20]([CH2:23][N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH:26]([NH:34][C:35]([C:37]2[NH:38][C:39]3[C:44]([CH:45]=2)=[CH:43][C:42](Cl)=[CH:41][CH:40]=3)=[O:36])[C:25]1=[O:47])([OH:22])=[O:21]>C(Cl)Cl>[O:8]=[C:3]1[CH2:4][CH2:5][C:6](=[O:7])[N:2]1[O:22][C:20](=[O:21])[CH2:23][N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH:26]([NH:34][C:35]([C:37]2[NH:38][C:39]3[C:44]([CH:45]=2)=[CH:43][C:42]([CH3:9])=[CH:41][CH:40]=3)=[O:36])[C:25]1=[O:47]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 101266823,4-dihydro-2-quinolone (DHQ) derivative, 10

生成物 1

HCID 86598698N-(1-{2-[(2,5-Dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-5-methyl-1H-indole-2-carboxamide収率 101.7%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

N-Hydroxysuccinimide (496 mg, 4.31 mmol) and EDCI (1.04 g, 5.38 mmol) were added to a suspension of N-[1-(carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-5-chloroindole-2-carboxamide (Example 2, 1.71 g, 4.31 mmol)) in DCM (50 mL) and stirred for 18 hours. The suspension was evaporated and the residue partitioned between EtOAc:THF (4:1)(200 mL) and H2O. The organic was dried (Na2SO4), filtered and evaporated. The solid was triturated with refluxing Et2O (25 mL), filtered, washed with Et2O (25 mL) then hexane (25 mL) to afford the title compound (2.08 g, 98%) as a pale brown powder.

後処理

  1. customThe suspension was evaporated
  2. customthe residue partitioned between EtOAc:THF (4:1)(200 mL) and H2O
  3. dry with materialThe organic was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe solid was triturated with refluxing Et2O (25 mL)
  7. filtrationfiltered
  8. washwashed with Et2O (25 mL)

出典と根拠

ORDレコード
ord-170913225b06455c887ad962c7c13a8a
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07169927B2

反応ノート

読み込み中…

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