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

HRID 1817460Notes

Reaction equation

HRID 1817460 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][C:17]=1[O:23][CH3:24].C(N(CC)CC)C.ClC(Cl)(O[C:36](=[O:42])OC(Cl)(Cl)Cl)Cl.[S:44]1[CH:48]=[CH:47][N:46]=[C:45]1[CH:49]([NH2:51])[CH3:50]>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:51][CH:49]([C:45]2[S:44][CH:48]=[CH:47][N:46]=2)[CH3:50])=[O:42])=[CH:18][C:17]=1[O:23][CH3:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 198969851-(1,3-Thiazol-2-yl)ethan-1-amineHCID 597919824-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methoxyaniline

Product 1

HCID 10005373N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methoxyphenyl}-N'-[1-(1,3-thiazol-2-yl)ethyl]ureaYield 63.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-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-(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 (28 mg, yield 62%).

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-a3132fb412a84e8f8b751b62f4ba358c
Source dataset
uspto-grants-2009_10
Patent number
US07598258B2

Reaction notes

Loading…