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

HRID 1817457Notes

Reaction equation

HRID 1817457 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])=[CH:18][CH:17]=1.C(N(CC)CC)C.ClC(Cl)(O[C:34](=[O:40])OC(Cl)(Cl)Cl)Cl.[S:42]1[CH:46]=[CH:45][N:44]=[C:43]1[CH:47]([NH2:49])[CH3:48]>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:34]([NH:49][CH:47]([C:43]2[S:42][CH:46]=[CH:45][N:44]=2)[CH3:48])=[O:40])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 198969851-(1,3-Thiazol-2-yl)ethan-1-amine

Product 1

HCID 10433903N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-[1-(1,3-thiazol-2-yl)ethyl]ureaYield 78.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (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-(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 (36 mg, yield 78%).

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-590ec210f17843e8bd84448f0d412e1c
Source dataset
uspto-grants-2009_10
Patent number
US07598258B2

Reaction notes

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