Potassium Iodide → Ethyl 3-methyl-2-{2-oxo-3-(4-(pyridin-4-ylmethoxy)benzyl)imidazolidin-1-yl}-butyrate

HRID 1994305Notes

Reaction equation

HRID 1994305 reaction equation
[OH:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][N:9]([CH:12]([CH:18]([CH3:20])[CH3:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]2=[O:21])=[CH:4][CH:3]=1.Cl.Cl[CH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CS(C)=O>[CH3:19][CH:18]([CH3:20])[CH:12]([N:9]1[CH2:10][CH2:11][N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:26][C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)[C:8]1=[O:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 68541940HCID 68541940, compound

Product 1

HCID 68538692Ethyl 3-methyl-2-{2-oxo-3-(4-(pyridin-4-ylmethoxy)benzyl)imidazolidin-1-yl}-butyrateYield 73.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-(3-(4-hydroxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrate (50 mg; 0.15 mmol) was dissolved in DMSO (1 ml). 4-Chloromethylpyridine hydrochloride (39 mg; 0.23 mmol), potassium carbonate (86 mg; 0.62 mmol) and potassium iodide (8 mg, 0.4 mmol) were successively added thereto. The mixture was heated at 50° C. for 3 h. Cooling to RT was followed by partitioning between water (10 ml) and EtOAc (10 ml). The phases were separated and the aqueous phase was extracted with EtOAc (3×; 5 ml). The combined organic phases were dried over MgSO4, and the solvent was removed under reduced pressure. Purification of the residue by column chromatography (SiO2) resulted in ethyl 3-methyl-2-{2-oxo-3-(4-(pyridin-4-ylmethoxy)benzyl)imidazolidin-1-yl}-butyrate (45 mg; 0.11 mmol). MS: 412.50 (M+H); Rt: 1.04 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Workup

  1. temperatureCooling to RT
  2. customby partitioning between water (10 ml) and EtOAc (10 ml)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with EtOAc (3×; 5 ml)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. customPurification of the residue by column chromatography (SiO2)

Sources & evidence

ORD record
ord-876d6431d5cd460ca203aae8519928cc
Source dataset
uspto-grants-2010_01
Patent number
US07652143B2

Reaction notes

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