2-Methoxyethanol → HCID 9996670, compound

HRID 1837360Notes

Reaction equation

HRID 1837360 reaction equation
[CH2:1]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12](F)=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]=[CH:8][C:7]=1[C:19]#[N:20])[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH3:23][O:24][CH2:25][CH2:26][OH:27]>>[CH2:1]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:27][CH2:26][CH2:25][O:24][CH3:23])=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]=[CH:8][C:7]=1[C:19]#[N:20])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 23498092HCID 23498092, compound

Product 1

HCID 9996670HCID 9996670, compound

Procedure

A mixture of 4-butylamino-7-fluoro-6-methoxy-3-quinolinecarbonitrile (150 mg, 0.55 mmol) and sodium hydride (55 mg, 2.29 mmol) in 1.7 mL of 2-methoxyethanol is heated at reflux for 30 minutes then cooled to room temperature. The reaction mixture is partitioned between aqueous sodium bicarbonate and ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated in vacuo. Purification by preparative thin layer chromatography, eluting with 5% methanol in dichloromethane, followed by trituration with ethyl acetate, provides 135 mg of 4-butylamino-6-methoxy-7-(2-methoxyethoxy)-3-quinolinecarbonitrile, mp 99-102° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 30 minutes
  3. customThe reaction mixture is partitioned between aqueous sodium bicarbonate and ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by preparative thin layer chromatography
  8. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-7a0bf6b2209443b3adf584b90f177d05
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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