Methanol → 1-(3-Methyl-benzo[d]isoxazol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 2383812Notes

Reaction equation

HRID 2383812 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][N:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:18]=3[CH3:19])[C:9]2=[O:20])=[CH:4][C:3]=1[C:21](=[N:23][OH:24])[CH3:22].[H-].[Na+].CO>CN(C=O)C.C(Cl)(Cl)Cl>[CH3:22][C:21]1[C:3]2[CH:4]=[C:5]([N:8]3[CH2:12][CH2:11][N:10]([C:13]4[CH:14]=[N:15][CH:16]=[CH:17][C:18]=4[CH3:19])[C:9]3=[O:20])[CH:6]=[CH:7][C:2]=2[O:24][N:23]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 866493961-[4-Fluoro-3-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

Product 1

HCID 498722501-(3-Methyl-benzo[d]isoxazol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 14.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent2×

Procedure

1-[4-Fluoro-3-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (220 mg, 0.670 mmol) in DMF (5 mL) was added to a stirred mixture of NaH (19 mg, 0.804 mmol) in DMF (2 mL) under nitrogen atmosphere at 0° C. The resulting mixture was stirred at room temperature for 21 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ethylacetate and ice water. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (1% MeOH in CHCl3) afforded 28 mg of the product (14.5% yield).

Workup

  1. customThe reaction mixture was partitioned between ethylacetate and ice water
  2. washThe organic layer was washed with brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (1% MeOH in CHCl3)

Sources & evidence

ORD record
ord-6845d764a0294e1ba0fc8922f2518750
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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