Water → HCID 66998731, compound

HRID 559154Notes

Reaction equation

HRID 559154 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:31](=[O:32])[N:30]([CH3:33])[C:12]2[NH:13][C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([C:20](=[O:29])[CH2:21][NH:22][C:23](=O)[CH2:24][O:25][CH2:26][CH3:27])=[CH:16][CH:15]=3.O>OS(O)(=O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:31](=[O:32])[N:30]([CH3:33])[C:12]2[NH:13][C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([C:20]1[O:29][C:23]([CH2:24][O:25][CH2:26][CH3:27])=[N:22][CH:21]=1)=[CH:16][CH:15]=3

Participants

4

Reactant 2

HCID 962WaterHCID 66998296HCID 66998296, compound

Product 1

HCID 66998731HCID 66998731, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of compound A N-{2-[3-(2,4-dichlorophenyl)-1-methyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]-2-oxoethyl}-2-ethoxyacetamide (841 mg, 1.73 mmol) in 2 ml of H2SO4 is stirred at ambient temperature for 20 h. H2O is added, the mixture ie extracted with EtOAc and CH2Cl2, and the product is concentrated without drying. The product is adsorbed onto silica and purification is carried out by chromatography on a silica column, elution being carried out with EtOAc. The residue is taken up in Et2O, and the product is filtered and washed with a minimum amount of Et2O.

Workup

  1. extractionthe mixture ie extracted with EtOAc and CH2Cl2
  2. concentrationthe product is concentrated
  3. customwithout drying
  4. customThe product is adsorbed onto silica and purification
  5. washis carried out by chromatography on a silica column, elution
  6. filtrationthe product is filtered
  7. washwashed with a minimum amount of Et2O

Sources & evidence

ORD record
ord-2a32b84367a1411a9d538e43e36e9c1e
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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