Water → HCID 22708262, compound

HRID 353199Notes

Reaction equation

HRID 353199 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:23]=[CH:22][C:10]([O:11][C:12]([CH3:21])([CH3:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:9][CH:8]=1.Br[CH2:25][C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:31][C:30]=1[C:38]([F:41])([F:40])[F:39])=[O:27].C(=O)(O)[O-].[Na+].O>CN(C)C=O>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:6][C:7]1[CH:23]=[CH:22][C:10]([O:11][C:12]([CH3:21])([CH3:20])[C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])=[CH:9][CH:8]=1)[CH2:25][C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:31][C:30]=1[C:38]([F:39])([F:40])[F:41])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 22708166HCID 22708166, compoundHCID 22708283HCID 22708283, compound

Product 1

HCID 22708262HCID 22708262, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.533 g (1.65 mmol) of tert-butyl 2-(4-{[(2-methoxyethyl)amino]methyl}phenoxy)-2-methylpropanoate (Example III-33) is initially charged in 6 ml of dimethylformamide. At room temperature, 0.588 g (1.81 mmol) of 2-bromo-N-[4-isopropyl-2-(trifluoromethyl)phenyl]acetamide (Example III-17) and 0.152 g (1.81 mmol) of sodium bicarbonate are added. The mixture is set at 90° C. for 2 hours. The reaction mixture is then allowed to cool, and water is added. The mixture is extracted once with ethyl acetate and the organic phase is washed three times with water and once with saturated sodium chloride solution. The organic phase is dried over sodium sulphate and freed from the solvent under reduced pressure. The residue is purified chromatographically on silica gel (cyclohexane/ethyl acetate 4:1) and the product is then dried under reduced pressure. This gives 0.885 g (95% of theory) of the title compound.

Workup

  1. customAt room temperature
  2. temperatureto cool
  3. extractionThe mixture is extracted once with ethyl acetate
  4. washthe organic phase is washed three times with water
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. customThe residue is purified chromatographically on silica gel (cyclohexane/ethyl acetate 4:1)
  7. customthe product is then dried under reduced pressure

Sources & evidence

ORD record
ord-876685903ad64dc7b4d9eedb8aa85fe3
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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