Hydroxylamine → HCID 75952218, compound

HRID 1410154Notes

Reaction equation

[NH2:1][OH:2].[Br:3][C:4]1[N:8]([CH3:9])[C:7]([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]([CH3:26])[CH:5]=1>CO>[Br:3][C:4]1[N:8]([CH3:9])[C:7]([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]([CH3:26])[CH:5]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Hydroxylamine (16.3 M solution in water, 0.3 mL, 4.8 mmol) was added to 5-(5-bromo-1,3-dimethyl-1H-pyrrol-2-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (7 mg, 0.018 mmol) in MeOH (0.6 mL) and the reaction was stirred at 150° C. for 20 min in the microwave. The crude reaction was purified on preparative HPLC to give E9 5-(5-bromo-1,3-dimethyl-1H-pyrrol-2-yl)-1-(2-fluoro-4-hydroxyphenyl)-N′-hydroxy-3-methyl-1H-pyrazole-4-carboximidamide (2.47 mg, 33%). 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: 422.00, 424.00 (M+H), 420.09, 422.07 (M−H); 1H NMR (acetone-d6, 500 MHz): 8.11 (s, 1H), 7.20 (t, 1H, J=8.8 Hz), 6.86 (s, 1H), 6.70 (m, 1H), 6.62 (dd, 1H, J=2.6, 11.9 Hz), 3.41 (s, 3H), 2.39 (s, 3H) and 1.66 (s, 3H).

Workup

customThe crude reaction
customwas purified on preparative HPLC

Sources & evidence

ORD record: ord-46983a7758a6425192519056815d07a2
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921402B2

Reaction notes

Loading…