Water → HCID 75952214, compound

HRID 1410138Notes

Reaction equation

HRID 1410138 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].O.[CH3:7][C:8]1[C:12]([C:13]2[N:17]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[N:16]=[C:15]([CH2:25][CH2:26][CH3:27])[C:14]=2[C:28]#[N:29])=[C:11]([CH3:30])[O:10][N:9]=1>CS(C)=O>[CH3:7][C:8]1[C:12]([C:13]2[N:17]([C:18]3[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=3)[N:16]=[C:15]([CH2:25][CH2:26][CH3:27])[C:14]=2[C:28](=[N:2][OH:3])[NH2:29])=[C:11]([CH3:30])[O:10][N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 67120061HCID 67120061, compound

Product 1

HCID 75952214HCID 75952214, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

A neutral 2 M solution of hydroxylamine hydrochloride and NaOH in water (0.5 mL, 1.0 mmol) was added to 5-(3,5-dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-3-propyl-1H-pyrazole-4-carbonitrile (5.4 mg, 0.017 mmol) in DMSO (0.5 mL) and stirred at 65° C. over night. Crude LCMS on the reaction mixture show 41% product, 38% amide and 21% starting material. Purification using preparative HPLC gave E5 5-(3,5-dimethylisoxazol-4-yl)-N′-hydroxy-1-(4-hydroxyphenyl)-3-propyl-1H-pyrazole-4-carboximidamide (1.42 mg, 24%). 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: 356.2 (M+H), 354.21 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.11 m 2H, 6.85 m 2H, 2.77 nm 2H, 2.11 s 3H, 1.88 s 3H, 1.75 m 2H, 0.98 t (7.5 Hz) 3H.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-222eb3e3f82c411384a0673143bbe941
Source dataset
uspto-grants-2014_12
Patent number
US08921402B2

Reaction notes

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