Dimethylamine → HCID 9865304, compound

HRID 1384806Notes

Reaction equation

HRID 1384806 reaction equation
[CH2:1]([N:3]1[C:11]2[CH:10]=[CH:9][C:8]([F:12])=[CH:7][C:6]=2[C:5]2[C:13]([CH2:24][C:25](O)=[O:26])=[N:14][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16](=[O:17])[C:4]1=2)[CH3:2].[C:28](N1C=CN=C1)([N:30]1C=CN=[CH:31]1)=O.CNC>O1CCCC1>[CH2:1]([N:3]1[C:11]2[CH:10]=[CH:9][C:8]([F:12])=[CH:7][C:6]=2[C:5]2[C:13]([CH2:24][C:25]([N:30]([CH3:31])[CH3:28])=[O:26])=[N:14][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16](=[O:17])[C:4]1=2)[CH3:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 21183735HCID 21183735, compound

Product 1

HCID 9865304HCID 9865304, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 1 g (2.73 mmol) of 5-ethyl-8-fluoro-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetic acid and of 0.7 g (4.3 mmol) of 1,1′-carbonylbis-1H-imidazole in 200 ml of tetrahydrofuran is stirred for 3 h at 50° C. The reaction mixture is cooled to 25° C., an excess of liquefied dimethylamine is added and the reaction mixture is stirred for 12 h at room temperature. It is concentrated under reduced pressure, 100 ml of dichloromethane and 100 ml of water are added and the organic phase is separated, washed with water, dried over magnesium sulphate and concentrated under reduced pressure. The resulting oil crystallizes from ether. After filtering and recrystallizing from ethyl acetate, 0.75 g (1.9 mmol) of white crystals is isolated.

Workup

  1. concentrationIt is concentrated under reduced pressure, 100 ml of dichloromethane and 100 ml of water
  2. additionare added
  3. customthe organic phase is separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting oil crystallizes from ether
  8. filtrationAfter filtering
  9. customrecrystallizing from ethyl acetate

Sources & evidence

ORD record
ord-9efcf21b73064a3bbac3571ac148fca1
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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