Methanol → HCID 49872151, compound

HRID 2383782Notes

Reaction equation

HRID 2383782 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[CH:10]=[C:9]([N:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:21]=3[CH3:22])[C:12]2=[O:23])[CH:8]=[CH:7][N:6]=1.CO>O1CCOCC1.C(Cl)(Cl)Cl>[CH3:1][O:2][C:5]1[CH:10]=[C:9]([N:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:21]=3[CH3:22])[C:12]2=[O:23])[CH:8]=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 49871869Cfg-920

Product 1

HCID 49872151HCID 49872151, compoundYield 30.61%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Sodium methoxide (225 mg, 4.165 mmol) was added dropwise to a stirred solution of 1-(2-chloro-pyridin-4-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (58A: 100 mg, 0.374 mmol) in 1,4-dioxane (20 mL) over a period of 10 minutes. The resulting mixture was heated to 110° C. and maintained at the same temperature for 4 days. The reaction was monitored by TLC (10% MeOH in CHCl3). The solvent was distilled from the reaction mixture and the concentrate was partitioned between water and ethylacetate. The organic layer was dried over Na2SO4 to afford the crude product. Purification by column preparative HPLC afforded 30 mg of the product (30.61% yield).

Workup

  1. temperaturemaintained at the same temperature for 4 days
  2. distillationThe solvent was distilled from the reaction mixture
  3. customthe concentrate was partitioned between water and ethylacetate
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customto afford the crude product
  6. customPurification by column preparative HPLC

Sources & evidence

ORD record
ord-f4d6ff99bd7147f29c388ebe2895e53f
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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