Triphosgene → N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluorophenyl}-N'-(2-propynyl)urea

HRID 1375846노트

반응식

HRID 1375846 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][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([F:23])[CH:17]=1.ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.Cl.[CH2:37]([NH2:40])[C:38]#[CH:39].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[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][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:28]([NH:40][CH2:37][C:38]#[CH:39])=[O:34])=[C:18]([F:23])[CH:17]=1

참가 물질

7

반응물 4

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 11205720Prop-2-ynylamine hydrochlorideHCID 218902744-((6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoroaniline

생성물 1

HCID 22667153N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluorophenyl}-N'-(2-propynyl)urea수율 33.5%

시약·촉매·용매 2

HCID 6212Chloroform용매2회HCID 8471Triethylamine용매

실험 절차

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoroaniline (50 mg) was dissolved in chloroform (3 ml) and triethylamine (0.3 ml), and a solution of triphosgene (47 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, propargylamine hydrochloride (29 mg) was added to the reaction solution, and the mixture was further stirred at room temperature overnight. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was washed with chloroform to give 21 mg (yield 33%) of the title compound.

후처리

  1. stirringthe mixture was further stirred at room temperature overnight
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. washThe residue was washed with chloroform

출처 및 근거

ORD 기록
ord-6681d1f6c3d442959e6d4878d9769245
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169789B2

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