Hydroxylamine → HCID 136350244, compound

HRID 242214Notes

Reaction equation

HRID 242214 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[C:8]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[N:9][N:10]([CH3:14])[C:11]=2[C:12]#[N:13])=[C:5]([CH3:22])[O:4][N:3]=1.[NH2:23][OH:24].CCOC(C)=O.O>CS(C)=O>[CH3:1][C:2]1[C:6]([C:7]2[C:8]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[N:9][N:10]([CH3:14])[C:11]=2[C:12](=[N:23][OH:24])[NH2:13])=[C:5]([CH3:22])[O:4][N:3]=1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 962WaterHCID 8857Ethyl AcetateHCID 136350245HCID 136350245, compound

Product 1

HCID 136350244HCID 136350244, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 4-(3,5-dimethylisoxazol-4-yl)-3-(4-hydroxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile in DMSO (1.5 mL) was added neutral hydroxylamine solution (2 M in water, 1.27 mL, 2.55 mmol) and stirred at 130° C. for 10 min. EtOAc and water were added and the phases were separated. The crude product was purified on preparative HPLC to give E13 4-(3,5-dimethylisoxazol-4-yl)-N′-hydroxy-3-(4-hydroxyphenyl)-1-methyl-1H-pyrazole-5-carboximidamide (11.3 mg, 0.035 mmol, 34%) ES/MS m/z: 328.1 (M+H), 326.5 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.29 (m, 2H), 6.78 (m, 2H), 3.95 (s, 3H), 2.10 (s, 3H) and 1.88 (s, 3H), and E14 4-(3,5-dimethylisoxazol-4-yl)-3-(4-hydroxyphenyl)-1-methyl-1H-pyrazole-5-carboxamide (12.7 mg, 0.041 mmol, 40%), ES/MS m/z: 313.1 (M+H), 311.5 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.25 (m, 2H), 6.79 (m, 2H), 4.11 (s, 3H), 2.11 (s, 3H) and 1.92 (s, 3H).

Workup

  1. customthe phases were separated
  2. customThe crude product was purified on preparative HPLC

Sources & evidence

ORD record
ord-016f4d3ac9854ee7b6250006a82a04a1
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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