Water → HCID 9910161, compound

HRID 1384838Notes

Reaction equation

HRID 1384838 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C[Al](C)C.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[C:15]3[C:24]([CH2:25][C:26](OC)=[O:27])=[N:23][N:22]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:21](=[O:36])[C:16]=3[N:17]([CH3:20])[C:18]=2[CH:19]=1.O>C1(C)C=CC=CC=1.ClCCl>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[C:15]3[C:24]([CH2:25][C:26]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[O:27])=[N:23][N:22]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:21](=[O:36])[C:16]=3[N:17]([CH3:20])[C:18]=2[CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 15461904HCID 15461904, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 9910161HCID 9910161, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

0.41 ml (4 mmol) of diethylamine is added at 0° C. under argon to a solution of 2 ml (4 mmol) of trimethylaluminium (2M in toluene) in 30 ml of toluene, the reaction mixture is stirred for 20 min at room temperature, 0.095 g (0.25 mmol) of methyl 7-chloro-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]-indole-1-acetate is added and the reaction mixture is stirred for 4 h at reflux. The mixture is cooled to 4° C., 3 ml of water and dichloromethane are added, the solution is filtered and the filtrate is concentrated under reduced pressure. Water, 1M hydrochloric acid and 150 ml of dichloromethane are added to the residue, the organic phase is separated, washed with water, dried over sodium sulphate, filtered and concentrated under reduced pressure and the residue is purified by chromatography on a column of silica gel. After recrystallization from diethyl ether, 0.10 g (0.24 mmol) of compound is isolated in the form of a white solid with a fluffy appearance.

Workup

  1. stirringthe reaction mixture is stirred for 4 h
  2. temperatureat reflux
  3. temperatureThe mixture is cooled to 4° C.
  4. filtrationthe solution is filtered
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. additionWater, 1M hydrochloric acid and 150 ml of dichloromethane are added to the residue
  7. customthe organic phase is separated
  8. washwashed with water
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customthe residue is purified by chromatography on a column of silica gel
  13. customAfter recrystallization from diethyl ether

Sources & evidence

ORD record
ord-8594041da0f54f0d844bc8944120bd7a
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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