Triethylamine → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylphenyl}-N'-[5-(ethylsulfanyl)-1,3,4-thiadiazol-2-yl]urea

HRID 1348879노트

반응식

HRID 1348879 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([CH3:23])[C:17]=1[CH3:24].C(N(CC)CC)C.ClC(Cl)(O[C:36](=[O:42])OC(Cl)(Cl)Cl)Cl.[NH2:44][C:45]1[S:46][C:47]([S:50][CH2:51][CH3:52])=[N:48][N:49]=1>C(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:36]([NH:44][C:45]2[S:46][C:47]([S:50][CH2:51][CH3:52])=[N:48][N:49]=2)=[O:42])=[C:18]([CH3:23])[C:17]=1[CH3:24]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 1014591,3,4-Thiadiazol-2-amine, 5-(ethylthio)-HCID 218904394-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline

생성물 1

HCID 23118586N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylphenyl}-N'-[5-(ethylsulfanyl)-1,3,4-thiadiazol-2-yl]urea수율 33.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매2회

실험 절차

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (100 mg) was dissolved in chloroform (5 ml) and triethylamine (0.5 ml) to prepare a solution. A solution of triphosgene (100 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 15 min. Next, 2-amino-5-ethylthio-1,3,4-thiadiazole (60 mg) was added thereto, and the mixture was further stirred at room temperature overnight. Distilled water was added to the reaction solution, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine and was dried over sodium sulfate. The organic layer was concentrated under the reduced pressure, and the residue was purified by HPLC using chloroform/acetone for development to give 53 mg of the title compound.

후처리

  1. stirringthe mixture was further stirred at room temperature overnight
  2. extractionthe mixture was subjected to separatory extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialwas dried over sodium sulfate
  5. concentrationThe organic layer was concentrated under the reduced pressure
  6. customthe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-7c7a1270747a4f9aa5903c011871b991
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07211587B2

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