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

HRID 1817474Notes

Reaction equation

HRID 1817474 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]([F:23])[CH:17]=1.C(N(CC)CC)C.ClC(Cl)(O[C:35](=[O:41])OC(Cl)(Cl)Cl)Cl.[CH3:43][C:44]1[N:45]=[C:46]([CH:50]([NH2:52])[CH3:51])[S:47][C:48]=1[CH3:49]>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:35]([NH:52][CH:50]([C:46]2[S:47][C:48]([CH3:49])=[C:44]([CH3:43])[N:45]=2)[CH3:51])=[O:41])=[C:18]([F:23])[CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroanilineHCID 242616561-(4,5-Dimethylthiazol-2-yl)ethanamine

Product 1

HCID 10413493N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}-N'-[1-(4,5-dimethyl-1,3-thiazol-2-yl)ethyl]ureaYield 38%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (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-(4,5-dimethyl-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 (18 mg, yield 38%).

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-65c1cd5fe75a458c8200e9f7c73d0580
Source dataset
uspto-grants-2009_10
Patent number
US07598258B2

Reaction notes

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