Triethylamine → HCID 57881608, compound

HRID 1817415Notes

Reaction equation

HRID 1817415 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[F:23].C(N(CC)CC)C.ClC(Cl)(O[C:35](=[O:41])OC(Cl)(Cl)Cl)Cl.[F:43][C:44]1[CH:49]=[CH:48][C:47]([C@@H:50]([NH2:52])[CH3:51])=[CH:46][CH:45]=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:22]=[CH:21][C:19]([NH:20][C:35]([NH:52][C@H:50]([C:47]2[CH:48]=[CH:49][C:44]([F:43])=[CH:45][CH:46]=2)[CH3:51])=[O:41])=[CH:18][C:17]=1[F:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamine

Product 1

HCID 57881608HCID 57881608, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-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 (1S)-1-(4-fluorophenyl)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 (27 mg, yield 59%).

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-f83b24a0f88742ffba77e8786862c9ec
Source dataset
uspto-grants-2009_10
Patent number
US07598258B2

Reaction notes

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