2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 69949070, compound

HRID 2268616Notes

Reaction equation

HRID 2268616 reaction equation
[C:1]([O:5][C:6]([N:8]([C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[C:15](O)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28][CH2:29][O:30][CH:31]1[N:40](C(OCC)=O)[C:39]2[C:34](=CC=CC=2)[CH:33]=[CH:32]1>C(#N)C>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:15](=[O:16])[N:8]([CH:22]([CH3:27])[CH3:23])[CH2:28][CH2:29][O:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:39][N:40]=2)[CH:18]=[C:19]([Cl:21])[CH:20]=1)[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 18348849Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-

Product 1

HCID 69949070HCID 69949070, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.10 g) isopropyl-2-(pyridin-2-yloxy)-ethylamine (0.18 g) and EEDQ (0.136 g) in acetonitrile (2 ml) was stirred at reflux, under nitrogen, for 18 h. The solvent was evaporated and the residue was purified by flash chromatography on silica eluting with dichloromethane/methanol (98:2 then 96:4) to give the title compound as a pale yellow oil (0.033 g).

Workup

  1. temperatureat reflux, under nitrogen, for 18 h
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography on silica eluting with dichloromethane/methanol (98:2

Sources & evidence

ORD record
ord-5bcb1c5151cf4a9bb9c79fac55ce8e2f
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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