Methanol → 1-(1H-indazol-6-yl)-3-(4-methylpyridin-3-yl)imidazolidin-2-one

HRID 80155Notes

Reaction equation

O.[NH2:2]N.CO[N:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:24]=3[CH3:25])[C:15]2=[O:26])=[CH:10][C:9]=1F.CO>C(Cl)(Cl)Cl>[NH:2]1[C:9]2[C:8](=[CH:13][CH:12]=[C:11]([N:14]3[CH2:18][CH2:17][N:16]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][C:24]=4[CH3:25])[C:15]3=[O:26])[CH:10]=2)[CH:7]=[N:6]1

Participants

Conditions

Temperature: 200 °C

Procedure

Hydrazine hydrate (5 mL) was added to solution of 2-fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde O-methyl-oxime (I-121b: 350 mg, 0.917 mmol) in 2-methoxy methanol (10 mL). The resulting mixture was heated to 200° C. and maintained for 2 days. The reaction was monitored by TLC (5% MeOH in CHCl3). The reaction mixture was cooled to room temperature and concentrated. The crude product was purified by column chromatography on silica gel (4% MeOH in CHCl3), washed with ether and dried to afford 105 mg of the product (39.17% yield).

Workup

temperaturemaintained for 2 days
temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated
customThe crude product was purified by column chromatography on silica gel (4% MeOH in CHCl3)
washwashed with ether
customdried

Sources & evidence

ORD record: ord-e2c82bb4f0224d2982c25dfbb10c90e7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE045173E1

Reaction notes

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