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

HRID 721457

Reaction equation

HRID 721457 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-bc0b5711270a4191bd331c5ff9dd074b
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Linked notes

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