Methanol → N'-{2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}-N-ethyl-N-propylurea
Reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.[CH2:36]([NH:38][CH2:39][CH2:40][CH3:41])[CH3:37].CO>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:5][C:3]=1[NH:4][C:28](=[O:34])[N:38]([CH2:36][CH3:37])[CH2:39][CH2:40][CH3:41]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-aniline 80 mg) was dissolved in chloroform (3 ml) and triethylamine (0.3 ml), and a solution of triphosgene (72 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 15 min. Next, N-ethylpropylamine (44 μl) was added to the reaction solution, and the mixture was stirred at room temperature for additional 30 min. Methanol was added to the reaction solution, and the mixture was purified by HPLC by development with chloroform/methanol. The solvent was removed by distillation. The resultant crystal was washed with hexane to give 40 mg (yield 37%) of the title compound.
Workup
- stirringthe mixture was stirred at room temperature for additional 30 min
- customthe mixture was purified by HPLC by development with chloroform/methanol
- customThe solvent was removed by distillation
- washThe resultant crystal was washed with hexane
Sources & evidence
- ORD record
- ord-ef4a40b359bc44eaaf3347b04146c2c1
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07169789B2
Reaction notes
Loading…