Potassium Carbonate → HCID 9843841, compound

HRID 380734Notes

Reaction equation

HRID 380734 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([OH:18])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[O:27]1[CH:32]2[CH:28]1[CH2:29][O:30][CH2:31]2>CN(C)C=O>[Cl:20][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:32]2[CH:28]([OH:27])[CH2:29][O:30][CH2:31]2)[CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 675113,6-Dioxabicyclo[3.1.0]hexaneHCID 18366000HCID 18366000, compound

Product 1

HCID 9843841HCID 9843841, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

400 mg (1.2 mmol) of N-(3,5-dichloropyridin-4-yl)-3-hydroxy-4-methoxybenzamide (starting compound A16) and 540 mg (3.85 mmol) of potassium carbonate are stirred under a nitrogen atmosphere at RT for 1 h in 5 ml of dimethylformamide. The mixture is heated to 120° C. and 115 mg (1.3 mmol) of 3,4-epoxytetrahydrofuran are added to the reaction mixture 4×at an interval of 6 h in each case. The mixture is concentrated, 50 ml of water are added, it is acidified with 2 N HCl and extracted with 3×50 ml of ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate, concentrated and the residue is chromatographed on silica gel [toluene/ethyl acetate=1:2]. The product-containing fractions are concentrated and the residue is crystallized from diethyl ether. 130 mg of the title compound of m.p. 183-185° C. are obtained.

Workup

  1. concentrationThe mixture is concentrated
  2. addition50 ml of water are added
  3. extractionextracted with 3×50 ml of ethyl acetate
  4. washThe combined organic phases are washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customthe residue is chromatographed on silica gel [toluene/ethyl acetate=1:2]
  8. concentrationThe product-containing fractions are concentrated
  9. customthe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-30ff32ad54624035afc3bd385e1059d8
Source dataset
uspto-grants-2001_10
Patent number
US06303789B1

Reaction notes

Loading…