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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
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반응식

HRID 1376155 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 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-carboxamide수율 101.7%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-170913225b06455c887ad962c7c13a8a
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07169927B2

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