HCID 10031247, compound → HCID 15051942, compound

HRID 847511Notes

Reaction equation

HRID 847511 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]1[C:11](=[O:42])[CH:12]([CH:15]([OH:41])[C:16]3[N:17]=[CH:18][N:19](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:20]=3[CH3:21])[CH2:13][CH2:14][C:6]1=[C:5]2[CH3:43]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]1[C:11](=[O:42])[CH:12]([CH:15]([OH:41])[C:16]3[N:17]=[CH:18][NH:19][C:20]=3[CH3:21])[CH2:13][CH2:14][C:6]1=[C:5]2[CH3:43]

Participants

3

Reactant 1

HCID 10031247HCID 10031247, compound

Product 1

HCID 15051942HCID 15051942, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

A solution of the mixture of two diastereoisomers of 2-chloro-8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one (0.50 g) in acetic acid-water (5:2, 7 ml) was stirred at 60° C. for 2 hours. After evaporation of the solvent, the residue was partitioned between water and chloroform and neutralized with an aqueous sodium hydroxide, to give precipitates. The organic layer and the precipitates were combined and chromatographed on silica gel eluted by chloroform-methanol (0-10% V/V), to give two isomers of 2-chloro-8,9-dihydro-10-methyl-7[(hydroxy)(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (0.037 g), respectively.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was partitioned between water and chloroform
  3. customto give
  4. customprecipitates
  5. customchromatographed on silica gel
  6. washeluted by chloroform-methanol (0-10% V/V)

Sources & evidence

ORD record
ord-9953b45e664a474f906fffe8dc5b5d7f
Source dataset
uspto-grants-1992_08
Patent number
US05141945

Reaction notes

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