Methanol → 1-(3-Methyl-benzo[d]isoxazol-6-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80142Notes

Reaction equation

HRID 80142 reaction equation
[H-].[Na+].CN(C=O)C.F[C:9]1[CH:10]=[C:11]([N:19]2[CH2:23][CH2:22][N:21]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][C:29]=3[CH3:30])[C:20]2=[O:31])[CH:12]=[CH:13][C:14]=1[C:15](=[N:17][OH:18])[CH3:16].CO>C(Cl)Cl>[CH3:16][C:15]1[C:14]2[CH:13]=[CH:12][C:11]([N:19]3[CH2:23][CH2:22][N:21]([C:24]4[CH:25]=[N:26][CH:27]=[CH:28][C:29]=4[CH3:30])[C:20]3=[O:31])=[CH:10][C:9]=2[O:18][N:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 866493971-[3-Fluoro-4-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

Product 1

HCID 596361841-(3-Methyl-benzo[d]isoxazol-6-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 10.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NaH (32.8 mg, 1.3705 mmol) and DMF (4 mL) was added to 1-[3-fluoro-4-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (111b: 150 mg, 0.4568 mmol). The resulting mixture was microwaved at 50° C. for 1 hour. The reaction was monitored by TLC (10% MeOH in DCM). The reaction mixture was partitioned between ice water and ethylacetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure. Purification by column chromatography on silica gel (5% MeOH in CHCl3) afforded 15 mg of the product (10.7% yield).

Workup

  1. customThe resulting mixture was microwaved at 50° C. for 1 hour
  2. customThe reaction mixture was partitioned between ice water and ethylacetate
  3. washThe organic layer was washed with water, brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by column chromatography on silica gel (5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-c7fdfbe7151a4b099a1dd4d5e3b16cc3
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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