Methanol → 6-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-1,2-dihydro-indazol-3-one

HRID 80173Notes

Reaction equation

O.[NH2:2][NH2:3].C[O:5][C:6](=O)[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.CO>C(Cl)(Cl)Cl>[CH3:24][C:23]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[N:15]1[CH2:16][CH2:17][N:13]([C:10]2[CH:9]=[C:8]3[C:7]([C:6](=[O:5])[NH:2][NH:3]3)=[CH:12][CH:11]=2)[C:14]1=[O:25]

Participants

Conditions

Temperature: 120 °C

Procedure

Hydrazine hydrate (10 mL) was added to 2-fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzoic acid methyl ester (I-135a: 350 mg, 1.06 mmol) and the resulting mixture was heated to 120° C. for 18 hours. 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 crude product. Purification by column chromatography on silica gel (10% MeOH in CHCl3), followed by preparative HPLC afforded 135 mg of the product (41.2% yield).

Workup

customThe reaction mixture was partitioned between ice water and ethylacetate
concentrationThe aqueous layer was concentrated
customto afford the crude product
customPurification by column chromatography on silica gel (10% MeOH in CHCl3)

Sources & evidence

ORD record: ord-b7e837cd1c13412683ab0b9d5c995a3a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE045173E1

Reaction notes

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