Dimethylamine → HCID 15838109, compound

HRID 1421222Notes

Reaction equation

HRID 1421222 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]1[C:12](=[O:25])[N:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH:14]=[C:15]([C:16]([OH:18])=O)[C:5]2=1.[CH3:26][NH:27][CH3:28].O>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]1[C:12](=[O:25])[N:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH:14]=[C:15]([C:16]([N:27]([CH3:28])[CH3:26])=[O:18])[C:5]2=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 18780532HCID 18780532, compound

Product 1

HCID 15838109HCID 15838109, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.5 g (7.4 mmol) of 6-fluoro-9-methyl-1-oxo-2-(pyridin-2-yl)-2,9-dihydro-1H-pyrido[3,4-b]indole-4-carboxylic acid and of 2.4 g (14.8 mmol) of N,N'-carbonyldiimidazole in 65 ml of N,N-dimethylformamide is stirred for 4 h. The reaction mixture is cooled and a large excess of liquefied dimethylamine is added. The mixture is stirred for 48 h at room temperature, poured into water and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulphate, and the solvent is evaporated under reduced pressure. The residue is purified by chromatography on a column of silica gel, elution being carried out with a mixture of dichloromethane and ethyl acetate. The product is recrystallized from ethyl acetate.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is purified by chromatography on a column of silica gel, elution
  7. additionbeing carried out with a mixture of dichloromethane and ethyl acetate
  8. customThe product is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6bbb6b34b47d417d8cfe5b763f3993e5
Source dataset
uspto-grants-2000_06
Patent number
US06075021

Reaction notes

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