Water → HCID 136350251, compound

HRID 242229Notes

Reaction equation

HRID 242229 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[C:8]([C:15]3[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=3)=[N:9][N:10]([CH3:14])[C:11]=2[CH:12]=O)=[C:5]([CH3:23])ON=1.Cl.[NH2:25][OH:26].N1C=CC=C[CH:28]=1.[OH2:33]>CCO.C(Cl)Cl>[CH3:1][C:2]1[O:33][CH:28]=[C:5]([CH3:23])[C:6]=1[C:7]1[C:8]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[N:9][N:10]([CH3:14])[C:11]=1[CH:12]=[N:25][OH:26]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 86668982HCID 86668982, compound

Product 1

HCID 136350251HCID 136350251, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(3,5-dimethylisoxazol-4-yl)-3-(4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carbaldehyde (20 mg, 0.07 mmol), hydroxylamine hydrochloride (93.8 mg, 1.35 mmol) and pyridine (164 μL, 2.02 mmol) in dry EtOH (1.6 mL) was heated at 120° C. for 15 minutes in the microwave. Water and DCM were added and the phases were separated. The crude product was purified on preparative HPLC to give 4-(2,4-dimethylfuran-3-yl)-3-(4-hydroxyphenyl)-1-methyl-1H-pyrazole-5-carbaldehyde oxime (6.2 mg, 30%). 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: 312.1 (M+H), 310.26 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.77 (s, 1H), 7.40 (m, 2H), 7.32 (q, 1H, J=1.0 Hz), 6.76 (m, 2H), 4.09 (s, 3H), 2.02 (s, 3H) and 1.63 (q, 3H, J=1.0 Hz).

Workup

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

Sources & evidence

ORD record
ord-0a980ada17224df18aa41082acbbad21
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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