Methanol → 1-(3-Methyl-1H-indazol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 2383805Notes

Reaction equation

HRID 2383805 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([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]=[CH:8][C:9]=1F)(=O)[CH3:2].CO.O.[NH2:27][NH2:28]>C(Cl)(Cl)Cl>[CH3:2][C:1]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([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:5]=2)[NH:28][N:27]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 687845751-(3-Acetyl-4-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

Product 1

HCID 1784283941-(3-Methyl-1H-indazol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 14%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-(3-Acetyl-4-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (160 mg, 0.513 mmol) in hydrazine hydrate (5 mL) was taken in a reaction flask and the flask was heated to reflux and maintained for 21 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, filtered and the filtrate was concentrated. Purification by column chromatography on silica gel (3% MeOH in CHCl3), followed by preparative HPLC afforded 22 mg of the product (14% yield).

Workup

  1. temperaturethe flask was heated
  2. temperatureto reflux
  3. temperaturemaintained for 21 hours
  4. customThe reaction mixture was partitioned between ethylacetate and water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customPurification by column chromatography on silica gel (3% MeOH in CHCl3)

Sources & evidence

ORD record
ord-be1f778b90ce447b95825ba7ab2cc38d
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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