Triethylamine → N-(3-Fluoro-4-{[6-methoxy-7-(3-morpholinopropoxy)-4-quinolyl]oxy}phenyl)-N'-[1-(4-fluorophenyl)ethyl]urea

HRID 1817444Notes

Reaction equation

HRID 1817444 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][CH:11]=1)[NH2:5].C(N(CC)CC)C.ClC(Cl)(O[C:43](=[O:49])OC(Cl)(Cl)Cl)Cl.[F:51][C:52]1[CH:57]=[CH:56][C:55]([CH:58]([NH2:60])[CH3:59])=[CH:54][CH:53]=1>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:43]([NH:60][CH:58]([C:55]2[CH:56]=[CH:57][C:52]([F:51])=[CH:53][CH:54]=2)[CH3:59])=[O:49])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 1230631-(4-Fluorophenyl)ethylamineHCID 469280403-Fluoro-4-(6-methoxy-7-(3-morpholinopropoxy)quinolin-4-yloxy)aniline

Product 1

HCID 23074131N-(3-Fluoro-4-{[6-methoxy-7-(3-morpholinopropoxy)-4-quinolyl]oxy}phenyl)-N'-[1-(4-fluorophenyl)ethyl]ureaYield 64.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

3-Fluoro-4-{[6-methoxy-7-(3-morpholinopropoxy)-4-quinolyl]oxy}-aniline (30 mg) was dissolved in chloroform (3 ml) and triethylamine (0.3 ml) to prepare a solution. A solution of triphosgene (17 mg) in chloroform (0.2 ml) was then added to the solution, and the mixture was stirred at room temperature for 25 min. Next, a solution of 1-(4-fluorophenyl)ethylamine (12 mg) in chloroform (0.2 ml) was added thereto, and the mixture was stirred at room temperature for 5 hr. The stirred mixture was purified by chromatography on silica gel using chloroform/methanol for development to give the title compound (22 mg, yield 52%).

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hr
  2. customThe stirred mixture was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c44d04053d9c4ea1bb8233abf1f77a28
Source dataset
uspto-grants-2009_10
Patent number
US07598258B2

Reaction notes

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