Triethylamine → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-methoxyphenyl}-N'-[1-(5-methyl-1,3-thiazol-2-yl)ethyl]urea

HRID 1817484Notes

Reaction equation

HRID 1817484 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]([O:23][CH3:24])[CH:17]=1.C(N(CC)CC)C.ClC(Cl)(O[C:36](=[O:42])OC(Cl)(Cl)Cl)Cl.[CH3:44][C:45]1[S:49][C:48]([CH:50]([NH2:52])[CH3:51])=[N:47][CH:46]=1>C(Cl)(Cl)Cl>[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:52][CH:50]([C:48]2[S:49][C:45]([CH3:44])=[CH:46][N:47]=2)[CH3:51])=[O:42])=[C:18]([O:23][CH3:24])[CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 218910314-((6,7-Dimethoxyquinolin-4-yl)oxy)-2-methoxyanilineHCID 242744731-(5-Methyl-1,3-thiazol-2-yl)ethan-1-amine

Product 1

HCID 10028704N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-methoxyphenyl}-N'-[1-(5-methyl-1,3-thiazol-2-yl)ethyl]ureaYield 83.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-methoxyaniline (30 mg) was dissolved in chloroform (1 ml) and triethylamine (0.1 ml) to prepare a solution. A solution of triphosgene (35 mg) in chloroform (0.2 ml) was then added to the solution, and the mixture was stirred at room temperature for one hr. Next, a solution of 1-(5-methyl-1,3-thiazol-2-yl)-1-ethylamine (35 mg) in chloroform (0.2 ml) was added thereto, and the mixture was stirred at room temperature for 10 hr. The stirred mixture was purified by chromatography on silica gel using chloroform/methanol for development to give the title compound (38 mg, yield 83%).

Workup

  1. stirringthe mixture was stirred at room temperature for 10 hr
  2. customThe stirred mixture was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e29c3fbb227d46569c294fd66873ff8f
Source dataset
uspto-grants-2009_10
Patent number
US07598258B2

Reaction notes

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