Ethyl Acetate → 1-{4-[(E)-1-(5-Chloro-6-oxo-1,6-dihydropyridin-2-yl)-2-cyclopentylethenyl]phenyl}urea

HRID 70610Notes

Reaction equation

HRID 70610 reaction equation
[O-:1][C:2]#[N:3].[K+].[NH2:5][C:6]1[CH:11]=[CH:10][C:9](/[C:12](/[C:19]2[NH:24][C:23](=[O:25])[C:22]([Cl:26])=[CH:21][CH:20]=2)=[CH:13]\[CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O.C(O)(=O)C>[Cl:26][C:22]1[C:23](=[O:25])[NH:24][C:19](/[C:12](/[C:9]2[CH:10]=[CH:11][C:6]([NH:5][C:2]([NH2:3])=[O:1])=[CH:7][CH:8]=2)=[CH:13]/[CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 11378442Potassium cyanateHCID 674008996-[(E)-1-(4-aminophenyl)-2-cyclopentylethenyl]-3-chloropyridin-2(1H)-one

Product 1

HCID 674003311-{4-[(E)-1-(5-Chloro-6-oxo-1,6-dihydropyridin-2-yl)-2-cyclopentylethenyl]phenyl}ureaYield 21.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of potassium cyanate (41 mg) in water (2 mL) was added to a solution of 6-[(E)-1-(4-aminophenyl)-2-cyclopentylethenyl]-3-chloropyridin-2(1H)-one obtained in Example 1-105(1) (153 mg) in acetic acid (2 mL)-water (1 mL), and the mixture was stirred at room temperature for 30 minutes. Saturated aqueous sodium bicarbonate and ethyl acetate were sequentially added to the reaction solution. The organic layer was separated, washed with saturated aqueous sodium bicarbonate and brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=9:1→8:2). This was powdered with ethyl acetate, and filtration operation gave the title compound as a light yellow powder (37 mg, 21%).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol=9:1→8:2)
  7. filtrationThis was powdered with ethyl acetate, and filtration operation

Sources & evidence

ORD record
ord-2fd832deabf445d0bc2ce613d8d09acc
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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