2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 54271774, compound

HRID 2268611Notes

Reaction equation

HRID 2268611 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].[CH:28]1([NH:33][CH2:34][CH2:35][CH2:36][CH2:37][N:38]2[CH:42]=[N:41][CH:40]=[N:39]2)[CH2:32][CH2:31][CH2:30][CH2:29]1.CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1>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:33]([CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:34][CH2:35][CH2:36][CH2:37][N:38]2[CH:42]=[N:41][CH:40]=[N:39]2)[CH:18]=[C:19]([Cl:21])[CH:20]=1)[C:22]1[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 18348849Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-HCID 18348925HCID 18348925, compound

Product 1

HCID 54271774HCID 54271774, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.040 g), cyclopentyl-(4-[1,2,4]triazol-1-yl-butyl)-amine (0.055 g) and EEDQ (0.050 g) in acetonitrile (2 ml) was stirred at reflux, under nitrogen, for 4 h. The solvent was evaporated and the residue was purified by flash chromatography eluting with dichloromethane:methanol:ammonia (95:5:0.5 then 90:10:1 v/v/v) to give the title compound as an orange oil (0.022 g).

Workup

  1. temperatureat reflux, under nitrogen, for 4 h
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography
  4. washeluting with dichloromethane:methanol:ammonia (95:5:0.5

Sources & evidence

ORD record
ord-468cd0e6d30a4f3ab5627cd5bba254ed
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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