Methanol → 1-[4-Fluoro-3-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80127Notes

Reaction equation

HRID 80127 reaction equation
Cl.[NH2:2][OH:3].[C:4]([C:7]1[CH:8]=[C:9]([N:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:24]=3[CH3:25])[C:15]2=[O:26])[CH:10]=[CH:11][C:12]=1[F:13])(=O)[CH3:5].CO>N1C=CC=CC=1.C(Cl)(Cl)Cl>[F:13][C:12]1[CH:11]=[CH:10][C:9]([N:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:24]=3[CH3:25])[C:15]2=[O:26])=[CH:8][C:7]=1[C:4](=[N:2][OH:3])[CH3:5]

Participants

6

Reactant 3

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 687845751-(3-Acetyl-4-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

Product 1

HCID 866493961-[4-Fluoro-3-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 95.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

LCMS purity: 99.03%, m/z=314.0 (M+1) Hydroxylamine hydrochloride (145 mg, 2.106 mmol) in pyridine (5 mL) was added to 1-(3-acetyl-4-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (220 mg, 0.702 mmol) under nitrogen atmosphere. The resulting mixture was stirred at room temperature for 18 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ethylacetate and water. The organic layer was dried over Na2SO4 and concentrated to afford 220 mg of 1-[4-Fluoro-3-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (90% yield).

Workup

  1. customThe reaction mixture was partitioned between ethylacetate and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-af27c052d13b49f0af24426e46171f80
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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