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

HRID 721455

Reaktionsgleichung

Reaktionsgleichung von HRID 721455
[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]([CH2:28][CH3:29])[CH2:26][CH3:27])=[S:31])=[CH:18][CH:17]=1

Komponenten

7

Edukt 4

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

Produkt 1

HCID 21889988N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-(3-diethylaminopropyl)thioureaAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (50 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 6 hr. Next, N,N-diethylpropylenediamine (50 mg) was added thereto, and the mixture was further stirred at room temperature for 15 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 (10 mg, yield 12%).

Aufarbeitung

  1. stirringthe mixture was further stirred at room temperature for 15 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

Quellen und Nachweise

ORD-Eintrag
ord-f6751be79ae04707bf0e40138e54490e
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135466B2

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