Triethylamine → HCID 57881567, compound

HRID 1817441Notes

Reaction equation

HRID 1817441 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.[Br:44][C:45]1[CH:46]=[C:47]([C@H:51]([NH2:53])[CH3:52])[CH:48]=[CH:49][CH:50]=1>C(Cl)(Cl)Cl>[Br:44][C:45]1[CH:46]=[C:47]([C@H:51]([NH:53][C:36]([NH:20][C:19]2[CH:21]=[CH:22][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[C:17]([O:23][CH3:24])[CH:18]=2)=[O:42])[CH3:52])[CH:48]=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 22831503176707-77-0HCID 597919824-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methoxyaniline

Product 1

HCID 57881567HCID 57881567, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methoxyaniline (79 mg) was dissolved in chloroform (2 ml) and triethylamine (0.2 ml) to prepare a solution. A solution of triphosgene (70 mg) in chloroform (0.4 ml) was then added to the solution, and the mixture was stirred at room temperature for one hr. Next, a solution of (1R)-1-(3-bromophenyl)ethylamine (70 mg) in chloroform (0.4 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 (39 mg, yield 29%).

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-86b7f1e1d8a5472cb83352a242ba1a14
Source dataset
uspto-grants-2009_10
Patent number
US07598258B2

Reaction notes

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