HCID 18332950, compound → HCID 21940038, compound

HRID 2269750Notes

Reaction equation

HRID 2269750 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([NH2:15])=[CH:11][CH:12]=2)[NH:7][C:6]1=O)=O>C1COCC1.O>[NH2:15][C:10]1[CH:9]=[C:8]2[C:13]([CH2:14][CH:5]([CH2:3][N:2]([CH3:17])[CH3:1])[CH2:6][NH:7]2)=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 18332950HCID 18332950, compound

Product 1

HCID 21940038HCID 21940038, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N,N-dimethyl-7-amino-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxamide (450 mg) in THF (15 ml) was added Borane-THF complex (1M, 12 ml) under ice-cooling. The reaction mixture was heated under reflux for one hour. The reaction mixture was diluted with water (2 ml) under ice-cooling and concentrated. The residue was dissolved in methanol (12 ml), which was heated under reflux with 6N hydrochloric acid (4 ml) for 3 hours. After cooling, the reaction mixture was made basic and extracted with combined solution of THF and ethyl acetate. The organic layer was dried and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate to ethyl acetate/methanol=20:1) to obtain the entitled compound (380 mg).

Workup

  1. additionwas added Borane-THF complex (1M, 12 ml) under ice-
  2. temperaturecooling
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for one hour
  5. temperaturecooling
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in methanol (12 ml)
  8. temperaturewhich was heated
  9. temperatureunder reflux with 6N hydrochloric acid (4 ml) for 3 hours
  10. temperatureAfter cooling
  11. extractionextracted with combined solution of THF and ethyl acetate
  12. customThe organic layer was dried
  13. concentrationconcentrated
  14. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate to ethyl acetate/methanol=20:1)

Sources & evidence

ORD record
ord-0ff35b603370464f8b292c01df4d252d
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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