Triethylamine → N-[1-(3,4-Difluorophenyl)ethyl]-N'-(2-fluoro-4-{[6-methoxy-7-(3-morpholinopropoxy)-4-quinolyl]oxy}phenyl)urea

HRID 1817448Notes

Reaction equation

HRID 1817448 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH2:23][CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.ClC(Cl)(O[C:43](=[O:49])OC(Cl)(Cl)Cl)Cl.[F:51][C:52]1[CH:53]=[C:54]([CH:59]([NH2:61])[CH3:60])[CH:55]=[CH:56][C:57]=1[F:58]>C(Cl)(Cl)Cl>[F:51][C:52]1[CH:53]=[C:54]([CH:59]([NH:61][C:43]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([O:9][C:10]3[C:19]4[C:14](=[CH:15][C:16]([O:22][CH2:23][CH2:24][CH2:25][N:26]5[CH2:27][CH2:28][O:29][CH2:30][CH2:31]5)=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]=[CH:12][CH:11]=3)=[CH:8][C:2]=2[F:1])=[O:49])[CH3:60])[CH:55]=[CH:56][C:57]=1[F:58]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 38159741-(3,4-Difluorophenyl)ethanamineHCID 690579052-Fluoro-4-{[6-methoxy-7-(3-morpholinopropoxy)-4-quinolyl]oxy}-aniline

Product 1

HCID 10371541N-[1-(3,4-Difluorophenyl)ethyl]-N'-(2-fluoro-4-{[6-methoxy-7-(3-morpholinopropoxy)-4-quinolyl]oxy}phenyl)ureaYield 77.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

2-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-(3,4-difluorophenyl)ethylamine (14 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 (27 mg, yield 60%).

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-ff61ca87a7114d0fa029322f29caa7a0
Source dataset
uspto-grants-2009_10
Patent number
US07598258B2

Reaction notes

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