1,2-Ethanediamine, N1,N1-bis(1-methylethyl)- → N-{2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-[2-(diisopropylamino)ethyl]urea

HRID 721554Notes

Reaction equation

HRID 721554 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].C(N(CC)CC)C.ClC(Cl)(O[C:35](=[O:41])OC(Cl)(Cl)Cl)Cl.[CH:43]([N:46]([CH:50]([CH3:52])[CH3:51])[CH2:47][CH2:48][NH2:49])([CH3:45])[CH3:44]>C(Cl)(Cl)Cl.O>[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:35]([NH:49][CH2:48][CH2:47][N:46]([CH:50]([CH3:52])[CH3:51])[CH:43]([CH3:45])[CH3:44])=[O:41]

Participants

7

Reactant 4

HCID 84591,2-Ethanediamine, N1,N1-bis(1-methylethyl)-HCID 8471TriethylamineHCID 94429TriphosgeneHCID 218898992-Chloro-4-((6,7-dimethoxyquinazolin-4-yl)oxy)aniline

Product 1

HCID 21889923N-{2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-[2-(diisopropylamino)ethyl]ureaYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-aniline (100 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml) to prepare a solution. A solution of triphosgene (134 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 10 min. Next, N1,N1-diisopropyl-1,2-ethanediamine (65 mg) was added thereto, and the mixture was further stirred at room temperature for one hr. Water was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by concentration. The residue was purified on a column using chloroform/methanol to give the title compound (64 mg, yield 43%).

Workup

  1. stirringthe mixture was further stirred at room temperature for one hr
  2. customthe reaction
  3. extractionthe reaction solution was then extracted with chloroform
  4. concentrationfollowed by concentration
  5. customThe residue was purified on a column

Sources & evidence

ORD record
ord-a7d2937793e145159f0cb275d2a99639
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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