Hydroxylamine → 5-(2,5-dimethyl-1H-pyrrol-1-yl)-1-(2-fluoro-4-hydroxyphenyl)-N'-hydroxy-3-methyl-1H-pyrazole-4-carboximidamide

HRID 1410143Notes

Reaction equation

[NH2:1][OH:2].[CH3:3][C:4]1[N:5]([C:10]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=3[F:22])[N:13]=[C:12]([CH3:23])[C:11]=2[C:24]#[N:25])[C:6]([CH3:9])=[CH:7][CH:8]=1>CO>[CH3:3][C:4]1[N:5]([C:10]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=3[F:22])[N:13]=[C:12]([CH3:23])[C:11]=2[C:24](=[N:1][OH:2])[NH2:25])[C:6]([CH3:9])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Hydroxylamine (50 wt % solution in water, 0.8 mL, 13.5 mmol) was added to 5-(2,5-dimethyl-1H-pyrrol-1-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (28 mg, 0.09 mmol) dissolved in MeOH (1.6 mL). The reaction was heated at 150° C. in the microwave for 15 min. Purification using preparative HPLC gave 5-(2,5-dimethyl-1H-pyrrol-1-yl)-1-(2-fluoro-4-hydroxyphenyl)-N′-hydroxy-3-methyl-1H-pyrazole-4-carboximidamide (8.68 mg, 28%). Identification of the title compound by 1H-NMR showed that the oxime product was a single isomer, but did not confirm whether the (E) or (Z) oxime isomer had been obtained. ES/MS m/z: 344.14 (M+H), 342.25 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.13 (t, 1H, J=8.5 Hz), 6.68 (m, 2H), 5.76 (s, 2H), 2.40 (s, 3H) and 1.95 (s, 6H).

Workup

customPurification

Sources & evidence

ORD record: ord-064672e5a40a44c498a57fd9650ca5ff
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921402B2

Reaction notes

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