Water → HCID 58875338, compound

HRID 2080233Notes

Reaction equation

HRID 2080233 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][NH:6][C:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[CH:12]2)=[O:8].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].O>ClCCl>[CH3:5][CH:4]([CH3:19])[CH2:3][CH2:2][O:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][NH:6][C:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[CH:12]2)=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 58875319HCID 58875319, compound

Product 1

HCID 58875338HCID 58875338, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture solution of quinoline-6-carboxylic acid 3-hydroxybenzylamide described in Preparation Example E+-4 (13 mg, 0.048 mmol) and N,N-dimethylformamide (0.5 mL) were added potassium carbonate (13 mg, 0.096 mmol) and 1-iodine-3-methylbutane (0.013 mL, 0.096 mmol), and the solution was stirred overnight at room temperature. Water and dichloromethane was added to the reaction solution for extraction, which was then washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate), and the title compound (12 mg, 0.033 mmol, 69%) was obtained as a colorless oil.

Workup

  1. washwas then washed with brine
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-66516ee0938b4ca0a7d22384d4eeb33d
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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