Hydroxylamine → HCID 75952259, compound

HRID 242209Notes

Reaction equation

HRID 242209 reaction equation
[NH2:1][OH:2].[CH2:3]([C:5]1[C:9]([C:10]#[N:11])=[C:8]([C:12]2[O:13][CH:14]=[CH:15][C:16]=2[CH3:17])[N:7]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[N:6]=1)[CH3:4]>CO>[CH2:3]([C:5]1[C:9]([C:10](=[N:1][OH:2])[NH2:11])=[C:8]([C:12]2[O:13][CH:14]=[CH:15][C:16]=2[CH3:17])[N:7]([C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)[N:6]=1)[CH3:4]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 67120046HCID 67120046, compound

Product 1

HCID 75952259HCID 75952259, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

Hydroxylamine (16.3 M solution in water, 0.3 mL, 4.8 mmol) was added to 3-ethyl-1-(4-hydroxyphenyl)-5-(3-methylfuran-2-yl)-1H-pyrazole-4-carbonitrile (5 mg, 0.02 mmol) in MeOH (0.6 mL) and the reaction was stirred at 150° C. for 20 min in the microwave reactor. The crude reaction was purified on preparative HPLC to give 3-ethyl-N′-hydroxy-1-(4-hydroxyphenyl)-5-(3-methylfuran-2-yl)-1H-pyrazole-4-carboximidamide (3.34 mg, 63%). 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: 327.1 (M+H), 325.23 (M−H); 1H NMR (acetone-d6, 500 MHz): 8.13 (s, 1H), 7.53 (d, 1H, J=1.9 Hz), 7.05 (m, 2H), 6.80 (m, 2H), 6.36 (d, 2H, J=1.9 Hz), 2.83 (q, 2H, J=7.6 Hz), 1.76 (s, 3H), and 1.26 (t, 3H, J=7.6 Hz).

Workup

  1. customThe crude reaction
  2. customwas purified on preparative HPLC

Sources & evidence

ORD record
ord-4cd87d850e5e44eb97062850fcaa8567
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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