Methanol → HCID 9841990, compound

HRID 1884584Notes

Reaction equation

HRID 1884584 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][CH:26]=1)[O:7][C:8]1[C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)([OH:3])=[O:2].CO.[C:29](OCC)(=O)C>C(Cl)Cl>[CH3:29][O:2][C:1]([C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][CH:26]=1)[O:7][C:8]1[C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 8857Ethyl AcetateHCID 235062692-(3-Carboxyphenoxy)-3-[3-(pyridin-4-yl)propoxy]pyridine

Product 1

HCID 9841990HCID 9841990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Carboxyphenoxy)-3-[3-(pyridin-4-yl)propoxy]pyridine (0.20 g, 0.57 mmol) obtained in Example 52 is dissolved in methylene chloride (10 ml), and thereto are added 1-ethyl-3-(3′-dimethyl aminopropyl)-carbodiimide.hydrochloride (0.13 g, 0.68 mmol) and methanol (0.10 ml), and the mixture is stirred at room temperature for 2 hours. To the reaction solution is added ethyl acetate (100 ml), and the mixture is washed with a saturated brine (30 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: chloroform/methanol) to give the title compound (0.17 g) as colorless oil.

Workup

  1. washthe mixture is washed with a saturated brine (30 ml×2)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-0fe2d3d600c54f23a96656e9d2937b93
Source dataset
uspto-grants-2004_07
Patent number
US06765095B2

Reaction notes

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