HCID 10031121, compound → HCID 15051926, compound

HRID 847495Notes

Reaction equation

HRID 847495 reaction equation
[OH:1][CH:2]([C:20]1[N:21]=[CH:22][N:23](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:24]=1[CH3:25])[CH:3]1[C:18](=[O:19])[N:7]2[C:8]3[C:13]([C:14]([CH2:15][CH2:16][CH3:17])=[C:6]2[CH2:5][CH2:4]1)=[CH:12][CH:11]=[CH:10][CH:9]=3>C(O)(=O)C.O>[OH:1][CH:2]([C:20]1[N:21]=[CH:22][NH:23][C:24]=1[CH3:25])[CH:3]1[C:18](=[O:19])[N:7]2[C:8]3[C:13]([C:14]([CH2:15][CH2:16][CH3:17])=[C:6]2[CH2:5][CH2:4]1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

4

Reactant 1

HCID 10031121HCID 10031121, compound

Product 1

HCID 15051926HCID 15051926, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-propylpyrido[1,2-a]-indol-6(7H)-one (1.65 g) in a mixture of acetic acid and water (4:1, 90 ml) was stirred at 60° C. for 4 hours. After evaporation of the solvent, the residue was diluted with as aqueous sodium bicarbonate solution and extracted three times with methylene chloride. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The crystalline residue was suspended in a mixture of methanol and chloroform and filtered to give one isomer of 8,9-dihydro-7-[(hydroxy)(5-methyl-1H-imidazol-4-yl)methyl]-10-propylpyrido[1,2-a]indol-6(7H)-one with an upper Rf value in silica gel thin layer chromatography (TLC) (6% methanol-chloroform) (0.27 g), which was designated as the isomer A. The filtrate was evaporated and purified by silica gel column chromatography (6% methanol-methylene chloride). The fractions eluted first contained the isomer A and the fractions eluted later contained another isomer of 8,9-dihydro-7-[(hydroxy)(5-methyl-1H-imidazol-4-yl)methyl]-10-propylpyrido[1,2-a]indol-6(7H)-one with a lower Rf value in TLC, which was designated as the isomer B.

Workup

  1. customAfter evaporation of the solvent
  2. additionthe residue was diluted with as aqueous sodium bicarbonate solution
  3. extractionextracted three times with methylene chloride
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. additionThe crystalline residue was suspended in a mixture of methanol and chloroform
  8. filtrationfiltered

Sources & evidence

ORD record
ord-595dfb688faa4accba83f933e03b3958
Source dataset
uspto-grants-1992_08
Patent number
US05141945

Reaction notes

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