Maleic Acid → 9-bromo-2-(3-hydroxypropyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one maleate

HRID 850815Notes

Reaction equation

HRID 850815 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:20](=[O:30])[C:21]([CH2:23][C:24]5[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=5)=[CH:22][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:10]=3.[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]\[C:34]([OH:36])=[O:35]>CO>[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]\[C:34]([OH:36])=[O:35].[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:20](=[O:30])[C:21]([CH2:23][C:24]5[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=5)=[CH:22][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:10]=3

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 98724899-bromo-2-(3-hydroxypropyloxy)-5-(3-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-one

Product 1

HCID 699514629-bromo-2-(3-hydroxypropyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one maleateYield 400.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

9-bromo-2-(3-hydroxypropyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (50 mg) obtained in Example 110 was suspended in methanol (100 ml) and to the suspension was added a solution of maleic acid (2.5 mg) in methanol (5 ml) at room temperature. The mixture was heated under reflux with stirring for 30 minutes and allowed to cool. The solvent was evaporated under reduced pressure, and the resulting crude crystals were washed with a small amount of methanol and ether in succession to obtain the title compound (50 mg, 80%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. temperatureto cool
  4. customThe solvent was evaporated under reduced pressure
  5. washthe resulting crude crystals were washed with a small amount of methanol and ether in succession

Sources & evidence

ORD record
ord-4cb32a6fbbe944b291dd9b23c26a223c
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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