Water → tert-butyl 2-[3-{[(4-chlorobenzyl)amino]carbonyl}-6-iodo-4-oxo-1(4H)-quinolinyl]acetate

HRID 1067958Notes

Reaction equation

HRID 1067958 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([I:21])=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:30]([O:34][C:35](=[O:38])[CH2:36]Br)([CH3:33])([CH3:32])[CH3:31].O>CN(C=O)C.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([I:21])[CH:17]=3)[N:12]([CH2:36][C:35]([O:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:38])[CH:11]=2)=[O:9])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 178522879HCID 178522879, compound

Product 1

HCID 21192561tert-butyl 2-[3-{[(4-chlorobenzyl)amino]carbonyl}-6-iodo-4-oxo-1(4H)-quinolinyl]acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a flask containing N-(4-chlorobenzyl)-6-iodo-4-hydoxy-3-quinolinecarboxamide (0.22 g) obtained as described in Preparation No. 4 in DMF (5 mL) is added potassium carbonate (0.21 g) and tert-butylbromoacetate (0.11 mL). After stirring overnight, the reaction is diluted with dichloromethane and partioned against water. The organic phase is washed with brine, dried over sodium sulfate, concentrated under reduced pressure, and dried in vacuo to give 0.26 g of the title compound as a white solid.

Workup

  1. customobtained
  2. customas described in Preparation No
  3. washThe organic phase is washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e51f622d595e419c9dd1f0f6c5f90c0d
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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