Triethylamine → HCID 57881597, compound

HRID 1817418Notes

Reaction equation

HRID 1817418 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][CH:17]=1.C(N(CC)CC)C.ClC(Cl)(O[C:34](=[O:40])OC(Cl)(Cl)Cl)Cl.Cl.[N+:43]([C:46]1[CH:51]=[CH:50][C:49]([C@@H:52]([NH2:54])[CH3:53])=[CH:48][CH:47]=1)([O-:45])=[O:44]>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:34]([NH:54][C@H:52]([C:49]2[CH:48]=[CH:47][C:46]([N+:43]([O-:45])=[O:44])=[CH:51][CH:50]=2)[CH3:53])=[O:40])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 16212176(1S)-1-(4-Nitrophenyl)ethan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 57881597HCID 57881597, compoundYield 127%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (70 mg) was dissolved in chloroform (1 ml) and triethylamine (0.14 ml) to prepare a solution. A solution of triphosgene (33 mg) in chloroform (0.2 ml) was then added to the solution, and the mixture was stirred at room temperature for 75 min. Next, a solution of (1S)-1-(4-nitrophenyl)ethylamine hydrochloride (47 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 (69 mg, yield 60%).

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-910a883b5aff49c4914d8a816d06a586
Source dataset
uspto-grants-2009_10
Patent number
US07598258B2

Reaction notes

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