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Triethylamine → N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-[3-(1-pyrrolidinyl)propyl]thiourea

HRID 721457
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HRID 721457 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])=[CH:18][CH:17]=1.[CH2:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH3:24].[C:30](Cl)(Cl)=[S:31].[CH2:34]([N:36](CC)CC(N)C)C>CN(C)C=O.C(OCC)(=O)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:30]([NH:36][CH2:34][CH2:24][CH2:23][N:25]2[CH2:28][CH2:29][CH2:27][CH2:26]2)=[S:31])=[CH:18][CH:17]=1
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 16643481(2-Aminopropyl)diethylamine

생성물 1

HCID 21890673N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-[3-(1-pyrrolidinyl)propyl]thiourea수율 24%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (51 mg) was dissolved in N,N-dimethylformamide (2 ml) and triethylamine (1 ml) to prepare a solution. Thiophosgene (50 mg) was then added to the solution, and the mixture was stirred at room temperature for 1 hr. Next, N,N-diethylpropylenediamine (50 mg) was added thereto, and the mixture was further stirred at room temperature for 6 hr. Ethyl acetate was added to the reaction solution, followed by washing with water and saturated brine in that order. The organic layer was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by HPLC using chloroform/methanol for development to give the title compound (19 mg, yield 24%).

후처리

  1. stirringthe mixture was further stirred at room temperature for 6 hr
  2. washby washing with water and saturated brine in that order
  3. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customthe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-bc0b5711270a4191bd331c5ff9dd074b
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07135466B2

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