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

HRID 2383830Notes

Reaction equation

HRID 2383830 reaction equation
F[C:2]1[CH:10]=[CH:9][C:8]([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:7][C:3]=1[CH:4]=[N:5][OH:6].[H-].[Na+].CO.C(Cl)Cl>CN(C=O)C.C(Cl)(Cl)Cl>[O:6]1[C:2]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:15][CH2:14][N:13]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][C:21]=4[CH3:22])[C:12]3=[O:23])=[CH:7][C:3]=2[CH:4]=[N:5]1

Participants

7

Reactant 4

HCID 887Methanol2×HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 866493992-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde oxime

Product 1

HCID 596361981-Benzo[d]isoxazol-5-yl-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 70.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent2×

Procedure

2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde oxime (I-113b: 160 mg, 0.509 mmol) in dry DMF (2 mL) was added dropwise to a stirred mixture of NaH (72 mg, 1.52 mmol) in DMF (1 mL) at 0° C. The resulting mixture was stirred at room temperature for 70 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ice water and ethylacetate. The aqueous layer was distilled to afford the solid residue which was dissolved 1:1 DCM: MeOH. The crude product was purified by column chromatography on silica gel (4-5% MeOH in CHCl3). The residue was washed with hexane and dried to afford 105 mg of the product (70.4% yield).

Workup

  1. customThe reaction mixture was partitioned between ice water and ethylacetate
  2. distillationThe aqueous layer was distilled
  3. customto afford the solid residue which
  4. customThe crude product was purified by column chromatography on silica gel (4-5% MeOH in CHCl3)
  5. washThe residue was washed with hexane
  6. customdried

Sources & evidence

ORD record
ord-af601d06046d4cf1858c921c448cb716
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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