Hydroxylamine → HCID 52914535, compound

HRID 1410147Notes

Reaction equation

[NH2:1][OH:2].[CH2:3]([N:5]([CH2:22][CH3:23])[C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[N:9]=[C:8]([CH2:18][CH3:19])[C:7]=1[C:20]#[N:21])[CH3:4]>CS(C)=O>[CH2:22]([N:5]([CH2:3][CH3:4])[C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[N:9]=[C:8]([CH2:18][CH3:19])[C:7]=1/[C:20](=[N:1]/[OH:2])/[NH2:21])[CH3:23]

Participants

Conditions

Temperature: 160 °C

Procedure

Hydroxylamine (50 wt % solution in water, 0.45 mL, 7.3 mmol) was added to 5-(diethylamino)-3-ethyl-1-(4-hydroxyphenyl)-1H-pyrazole-4-carbonitrile (16 mg, 0.06 mmol) dissolved in DMSO (1 mL) in a microwave vial. The reaction was heated at 160° C. in the microwave for 30 min. Purification using preparative HPLC gave (Z)-5-(diethylamino)-3-ethyl-N′-hydroxy-1-(4-hydroxyphenyl)-1H-pyrazole-4-carboximidamide (6.22 mg, 35%). Identification of the title compound by 1II-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: 318.29 (M+H), 316.32 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.40 (m, 2H), 6.90 (m, 2H), 2.96 (q, 4H, J=7.2 Hz), 2.65 (q, 2H, J=7.4 Hz), 1.19 (t, 3H, J=7.4 Hz) and 0.95 (t, 6H, J=7.2 Hz).

Workup

customPurification

Sources & evidence

ORD record: ord-a2f5baccea0a4ff3a26ffbb772be58e4
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921402B2

Reaction notes

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