Hydroxylamine → HCID 75952217, compound

HRID 1410153Notes

Reaction equation

HRID 1410153 reaction equation
[NH2:1][OH:2].[CH3:3][N:4]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:5]1[C:10]1[N:14]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[F:22])[N:13]=[C:12]([CH3:23])[C:11]=1[C:24]#[N:25]>CO>[CH3:3][N:4]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:5]1[C:10]1[N:14]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[F:22])[N:13]=[C:12]([CH3:23])[C:11]=1[C:24](=[N:1][OH:2])[NH2:25]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 67120064HCID 67120064, compound

Product 1

HCID 75952217HCID 75952217, compoundYield 39%

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 5-(1,3-dimethyl-1H-pyrrol-2-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (10 mg, 0.032 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 E8 5-(1,3-dimethyl-1H-pyrrol-2-yl)-1-(2-fluoro-4-hydroxyphenyl)-N′-hydroxy-3-methyl-1H-pyrazole-4-carboximidamide (4.27 mg, 39%). 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: 344.12 (M+H), 342.24 (M−H); 1H NMR (acetone-d6, 500 MHz): 8.11 (s, 1H), 7.17 (t, 1H, J=8.8 Hz), 6.70 (d, 1H, J=2.87 Hz), 6.67 (m, 1H), 6.61 (dd, 1H, J=2.6, 11.9 Hz), 5.83 (d, 1H, J=2.71), 3.38 (s, 3H), 2.39 (s, 3H) and 1.72 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-a8f0ea0a6f214cafae20c21c0090cf08
Source dataset
uspto-grants-2014_12
Patent number
US08921402B2

Reaction notes

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