Triethylamine → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2-diethylaminopropyl)thiourea

HRID 721498

Reaktionsgleichung

Reaktionsgleichung von HRID 721498
[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])=[CH:18][CH:17]=1.[CH2:23](N(CC)CC)C.[C:30](Cl)(Cl)=[S:31].[CH2:34]([N:36]([CH2:41][CH3:42])[CH2:37][CH:38]([NH2:40])C)[CH3:35]>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][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:30]([NH:40][CH2:38][CH:37]([N:36]([CH2:34][CH3:35])[CH2:41][CH3:42])[CH3:23])=[S:31])=[CH:18][CH:17]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 16643481(2-Aminopropyl)diethylamine

Produkt 1

HCID 21890370N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2-diethylaminopropyl)thiourea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (50 mg) was dissolved in N,N-dimethylformamide (2 ml) and triethylamine (1 ml) to prepare a solution. Thiophosgene (51 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 14 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 (25 mg, yield %).

Aufarbeitung

  1. stirringthe mixture was further stirred at room temperature for 14 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-6464900ee49a4b6caef9412bed6f0731
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135466B2

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