HCID 87276172, compound → HCID 67120023, compound

HRID 1410136Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[N:10]=[C:9]([CH2:20][CH2:21][CH3:22])[C:8]=2/[CH:23]=[N:24]/O)=[C:5]([CH3:26])[O:4][N:3]=1>C(OC(=O)C)(=O)C>[CH3:1][C:2]1[C:6]([C:7]2[N:11]([C:12]3[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=3)[N:10]=[C:9]([CH2:20][CH2:21][CH3:22])[C:8]=2[C:23]#[N:24])=[C:5]([CH3:26])[O:4][N:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

90% of the crude (E)-5-(3,5-dimethylisoxazol-4-yl)-1-(4-methoxyphenyl)-3-propyl-1H-pyrazole-4-carbaldehyde oxime (12 mg, 0.034 mmol) from step (e) was dissolved in acetic anhydride and heated at 140° C. for 40 minutes in the microwave. The reaction mixture was concentrated onto silica and filtered through a silica plug to give 5-(3,5-dimethylisoxazol-4-yl)-1-(4-methoxyphenyl)-3-propyl-1H-pyrazole-4-carbonitrile (12 mg, 100%).

Workup

concentrationThe reaction mixture was concentrated onto silica
filtrationfiltered through a silica plug

Sources & evidence

ORD record: ord-58907860055a4fe888c3e9147b62d182
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921402B2

Reaction notes

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