Methanol → HCID 178428392, compound

HRID 80130Notes

Reaction equation

HRID 80130 reaction equation
O.[NH2:2][NH2:3].[C:4]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:17][CH2:16][N:15]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[CH3:24])[C:14]2=[O:25])=[CH:9][C:8]=1F)(=O)[CH3:5].CO>C(Cl)(Cl)Cl>[CH3:5][C:4]1[C:7]2[C:8](=[CH:9][C:10]([N:13]3[CH2:17][CH2:16][N:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][C:23]=4[CH3:24])[C:14]3=[O:25])=[CH:11][CH:12]=2)[NH:3][N:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 687845161-(4-Acetyl-3-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

Product 1

HCID 178428392HCID 178428392, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

Hydrazine hydrate (10 mL) was added to 1-(4-acetyl-3-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (380 mg, 1.2128 mmol) under nitrogen atmosphere. The resulting mixture was stirred at 120° C. for 12 hours, cooled to room temperature and continued stirring for the next 12 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 (4% MeOH in CHCl3) afforded 240 mg of the product (64.5% yield).

Workup

  1. temperaturecooled to room temperature
  2. stirringcontinued stirring for the next 12 hours
  3. customThe reaction mixture was partitioned between ethylacetate and ice water
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (4% MeOH in CHCl3)

Sources & evidence

ORD record
ord-87b9b991d581407cb4ebcb720399bb50
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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