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

HRID 2383857Notes

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-a0127140607f49c29f048f809187d9ba
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263635B2

Reaction notes

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