Water → HCID 66997983, compound

HRID 559166Notes

Reaction equation

HRID 559166 reaction equation
C([O:8][CH2:9][C:10]([NH:12][CH2:13][C:14]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH3:25])[C:20]1[N:26]([CH3:39])[C:27](=[O:38])[C:28]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])=[CH:29][C:19]2=1)=O)=[O:11])C1C=CC=CC=1.O.CCOC(C)=O>OS(O)(=O)=O>[Cl:37][C:31]1[CH:32]=[C:33]([Cl:36])[CH:34]=[CH:35][C:30]=1[C:28]1[C:27](=[O:38])[N:26]([CH3:39])[C:20]2[N:21]([CH3:25])[C:22]3[C:18]([C:19]=2[CH:29]=1)=[CH:17][C:16]([C:14]1[O:11][C:10]([CH2:9][OH:8])=[N:12][CH:13]=1)=[CH:24][CH:23]=3

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 66998399HCID 66998399, compound

Product 1

HCID 66997983HCID 66997983, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of compound A 2-benzyloxy-N-{2-[3-(2,4-dichlorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]-2-oxoethyl}acetamide (454 mg, 0.81 mmol) in 2 ml of H2SO4 is stirred at ambient temperature for 20 h. A mixture of H2O and EtOAc is added, the green solid obtained is filtered off, the filtrate is taken up and extracted with EtOAc, and these combined organic phases are concentrated with the precipitate without drying. The product is adsorbed onto silica with a minimum amount of pyridine and purification is carried out by chromatography on a silica column, elution being carried out with EtOAc and then EtOAc/5% MeOH. The residue is taken up in MeOH and the product is filtered and washed with a minimum amount of MeOH and then of Et2O.

Workup

  1. additionis added
  2. customthe green solid obtained
  3. filtrationis filtered off
  4. extractionextracted with EtOAc
  5. concentrationthese combined organic phases are concentrated with the precipitate
  6. customwithout drying
  7. customThe product is adsorbed onto silica with a minimum amount of pyridine and purification
  8. washis carried out by chromatography on a silica column, elution
  9. filtrationthe product is filtered
  10. washwashed with a minimum amount of MeOH

Sources & evidence

ORD record
ord-467e39fc6a4f48f38eb172d8c41da9be
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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