1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-Chloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide

HRID 1376140

반응식

HRID 1376140 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:35][CH:36]1[CH2:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:38]([CH2:46][C:47]([O:49][CH3:50])=[O:48])[C:37]1=[O:51]>O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:35][CH:36]1[CH2:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]([CH2:46][C:47]([O:49][CH3:50])=[O:48])[C:37]1=[O:51])=[O:13])=[CH:5]2

참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 21974597Methyl (3-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate

생성물 1

HCID 101944715-Chloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

5-Chloro-1H-indole-2-carboxylic acid (493 mg, 2.52 mmol), HOBT (340 mg, 2.52 mmol), DCM (100 mL) and finally EDCI (483 mg, 2.52 mmol) were added to methyl 2-(3-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate (Method 1; 590 mg, 2.52 mmol) and the reaction was stirred for 18 h. The reaction was then diluted with water (50 mL) and stirred vigorously for 30 min. The resultant precipitate was filtered and washed with Et2O (2×20 mL). After filtration the resultant solid was then triturated with refluxing Et2O (25 mL) and after cooling the title compound (608 mg, 59%) was collected again by filtration as a white solid.

후처리

  1. stirringstirred vigorously for 30 min
  2. filtrationThe resultant precipitate was filtered
  3. washwashed with Et2O (2×20 mL)
  4. filtrationAfter filtration the resultant solid
  5. customwas then triturated with refluxing Et2O (25 mL)
  6. temperatureafter cooling the title compound (608 mg, 59%)
  7. filtrationwas collected again by filtration as a white solid

출처 및 근거

ORD 기록
ord-b0d586f9bdae4d878555e219d8b95831
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169927B2

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