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

HRID 1817470
Notes
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Reaction equation

HRID 1817470 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](OC)[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[N:46]=[C:47]([CH:50]([NH2:52])[CH3:51])[S:48][CH:49]=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:17]=[CH:18][C:19]([NH:20][C:36]([NH:52][CH:50]([C:47]2[S:48][CH:49]=[C:45]([CH3:44])[N:46]=2)[CH3:51])=[O:42])=[CH:21][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 45587211-(4-Methyl-1,3-thiazol-2-yl)ethan-1-amineHCID 218910314-((6,7-Dimethoxyquinolin-4-yl)oxy)-2-methoxyaniline

Product 1

HCID 10367179N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-[1-(4-methyl-1,3-thiazol-2-yl)ethyl]ureaYield 74.9%

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-(4-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 (32 mg, yield 68%).

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-f7ee1a204f464b679dbcf71c8c1bc6b4
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07598258B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes