Methanol → 5-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-1,2-dihydro-indazol-3-one

HRID 2383833Notes

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

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-a896e41a87b14f7f8e207c3579853e95
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263635B2

Reaction notes

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