Triethylamine → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylphenyl}-N'-[2-(ethyl-3-methylanilino)ethyl]urea

HRID 721560Notes

Reaction equation

HRID 721560 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][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([CH3:23])[C:17]=1[CH3:24].C(N(CC)CC)C.ClC(Cl)(O[C:36](=[O:42])OC(Cl)(Cl)Cl)Cl.[CH2:44]([N:46]([C:50]1[CH:55]=[CH:54][CH:53]=[C:52]([CH3:56])[CH:51]=1)[CH2:47][CH2:48][NH2:49])[CH3:45]>C(Cl)(Cl)Cl.O>[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:36]([NH:49][CH2:48][CH2:47][N:46]([CH2:44][CH3:45])[C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([CH3:56])[CH:51]=2)=[O:42])=[C:18]([CH3:23])[C:17]=1[CH3:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 879841,2-Ethanediamine, N1-ethyl-N1-(3-methylphenyl)-HCID 94429TriphosgeneHCID 218904394-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline

Product 1

HCID 21891046N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylphenyl}-N'-[2-(ethyl-3-methylanilino)ethyl]ureaYield 68.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (100 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml) to prepare a solution. A solution of triphosgene (139 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 10 min. Next, N1-ethyl-N1-(3-methylphenyl)-1,2-ethanediamine (84 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 (112 mg, yield 68%).

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-802be997d48b48e8a4a06c83716e640e
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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