2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 86586936, compound

HRID 2297649Notes

Reaction equation

HRID 2297649 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([C:21](O)=[O:22])[O:12]1.[CH3:24][C:25]([CH3:31])([CH3:30])[C:26]([NH:28][NH2:29])=[O:27].C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:24][C:25]([CH3:31])([CH3:30])[C:26]([NH:28][NH:29][C:21]([C@@H:13]1[C@@H:14]2[C@@H:15]([O:16][C:17]([CH3:19])([CH3:20])[O:18]2)[C@H:11]([N:6]2[CH:5]=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[Cl:1])[O:12]1)=[O:22])=[O:27]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 5451472,2-DimethylpropanehydrazideHCID 14374715HCID 14374715, compound

Product 1

HCID 86586936HCID 86586936, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 311Citric AcidSolvent

Procedure

(3aS,4S,6R,6aR)-6-(6-Chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2.5 g) suspended in 1,2-dimethoxymethane (100 ml) was treated with 2,2-dimethyl-propionic acid hydrazide (1.1 g) and 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), and the mixture heated under reflux for 16 h. The mixture was poured into aqueous citric acid (250 ml) and extracted with ethyl acetate; the organic layers were washed with citric acid and brine, dried (MgSO4) and evaporated in vacuo to give the crude product. Purification by flash chromatography on silica gel (Biotage cartridge), eluting with ethyl acetate:cyclohexane 65:35, gave the title compound as a white solid (1.92 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 16 h
  3. extractionextracted with ethyl acetate
  4. washthe organic layers were washed with citric acid and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customto give the crude product
  8. customPurification by flash chromatography on silica gel (Biotage cartridge)
  9. washeluting with ethyl acetate:cyclohexane 65:35

Sources & evidence

ORD record
ord-636460a5c3014ca48b904ef9cec4e65d
Source dataset
uspto-grants-2002_12
Patent number
US06492348B1

Reaction notes

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