Sodium Hydroxide → 10-bromo-2-(4-carboxy-1-piperidinocarbonylmethyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one

HRID 1530960Notes

Reaction equation

HRID 1530960 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:32]=[C:31]([CH2:33][C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)[C:30](=[O:40])[C:8]4[CH:9]=[C:10]([O:15][CH2:16][C:17]([N:19]5[CH2:24][CH2:23][CH:22]([C:25]([O:27]CC)=[O:26])[CH2:21][CH2:20]5)=[O:18])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:32]=[C:31]([CH2:33][C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)[C:30](=[O:40])[C:8]4[CH:9]=[C:10]([O:15][CH2:16][C:17]([N:19]5[CH2:20][CH2:21][CH:22]([C:25]([OH:27])=[O:26])[CH2:23][CH2:24]5)=[O:18])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1936485810-bromo-2-(4-ethoxycarbonyl-1-piperidinocarbonylmethyloxy)-5-(3-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-one

Product 1

HCID 1936486410-bromo-2-(4-carboxy-1-piperidinocarbonylmethyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10-bromo-2-(4-ethoxycarbonyl-1-piperidinocarbonylmethyloxy)-5-(3-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-one (250 mg) obtained in Example 45 was suspended in ethanol (30 ml), and to the suspension was added 1 N aqueous solution of sodium hydroxide (8 ml) and the mixture was stirred for 90 minutes at room temperature. After evaporate the solvent under reduced pressure, water and ethyl acetate were added to extract the mixture. The aqueous layer was adjusted to pH 6 by adding 1 N hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: methylene chloride/methanol=5:1). The crude purification product was washed with ether and recovered by filtration to obtain the title compound (100 mg, 42%).

Workup

  1. customAfter evaporate the solvent under reduced pressure, water and ethyl acetate
  2. additionwere added
  3. extractionto extract the mixture
  4. additionby adding 1 N hydrochloric acid
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel flash column chromatography (eluent: methylene chloride/methanol=5:1)
  10. customThe crude purification product
  11. washwas washed with ether
  12. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-a38d5befb84949b282633f40bbd1736b
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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