Methanol → 5-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-1,2-dihydro-indazol-3-one
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][N:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[CH3:21])[C:11]2=[O:22])[CH:7]=[CH:6][C:5]=1F.O.[NH2:26][NH2:27].CO>C(Cl)(Cl)Cl.C(Cl)Cl>[CH3:21][C:20]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[N:12]1[CH2:13][CH2:14][N:10]([C:8]2[CH:9]=[C:4]3[C:5](=[CH:6][CH:7]=2)[NH:27][NH:26][C:3]3=[O:2])[C:11]1=[O:22]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzoic acid methyl ester (I-117a: 510 mg, 1.55 mmol) and hydrazine hydrate were taken in a reaction flask and the flask was heated to 120° C. for 18 hours with stirring. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ice water and ethylacetate. The aqueous layer was concentrated to afford the solid residue which was dissolved in 1:1 DCM: MeOH and filtered. The filtrate was concentrated and purified by column chromatography on silica gel (10-15% MeOH in CHCl3). The residue was washed with DCM and dried to afford 180 mg of the product (37.6% yield).
Workup
- customThe reaction mixture was partitioned between ice water and ethylacetate
- concentrationThe aqueous layer was concentrated
- customto afford the solid residue which
- filtrationMeOH and filtered
- concentrationThe filtrate was concentrated
- custompurified by column chromatography on silica gel (10-15% MeOH in CHCl3)
- washThe residue was washed with DCM
- customdried
Sources & evidence
- ORD record
- ord-2d18caa59e3546e7850b387938850940
- Source dataset
- uspto-grants-2014_09
- Patent number
- USRE045173E1
Reaction notes
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