2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 69827870, compound

HRID 1839238Notes

Reaction equation

HRID 1839238 reaction equation
[CH:1]1([NH:6][C:7]2[N:15]=[CH:14][N:13]=[C:12]3[C:8]=2[N:9]=[CH:10][N:11]3[C@H:16]2[C@@H:20]3[O:21][C:22]([CH3:25])([CH3:24])[O:23][C@@H:19]3[C@@H:18]([C:26]([OH:28])=[O:27])[O:17]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:29](OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>CO>[CH3:29][O:27][C:26]([C@@H:18]1[C@@H:19]2[C@@H:20]([O:21][C:22]([CH3:24])([CH3:25])[O:23]2)[C@H:16]([N:11]2[CH:10]=[N:9][C:8]3[C:12]2=[N:13][CH:14]=[N:15][C:7]=3[NH:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[O:17]1)=[O:28]

Participants

4

Reactant 2

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 18336833HCID 18336833, compound

Product 1

HCID 69827870HCID 69827870, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3aS,4S,6R,6aR)-6-(6-cyclopentylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (3.018 g) and 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (2.66 g) in methanol (120 ml) was heated under reflux for 17 h. The resulting mixture was concentrated in vacuo and the residue dissolved in ethyl acetate (150 ml). The solution was washed with 0.5M aqueous citric acid solution (3×25 ml) and brine (50 ml), dried (magnesium sulphate), and evaporated in vacuo to give a white foam. Purification by column chromatography on silica gel, eluting with ethyl acetate:cyclohexane (1:1), gave the title compound as a white solid (2.32 g).

Workup

  1. temperatureunder reflux for 17 h
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate (150 ml)
  4. washThe solution was washed with 0.5M aqueous citric acid solution (3×25 ml) and brine (50 ml)
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated in vacuo
  7. customto give a white foam
  8. customPurification by column chromatography on silica gel
  9. washeluting with ethyl acetate:cyclohexane (1:1)

Sources & evidence

ORD record
ord-589d0fdeedda4aada00a36af4f0ce2f7
Source dataset
uspto-grants-2004_01
Patent number
US06677316B2

Reaction notes

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