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

HRID 1531019Notes

Reaction equation

HRID 1531019 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-0f0aee9465074685af209c2387647049
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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