1-[5-(4-t-Butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethanone → N'-{1-[5-(4-t-butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}-4-(1H-tetrazol-5-yl)benzhydrazide

HRID 1881606Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([CH3:16])[N:14]=[C:13]([C:17](=O)[CH3:18])[C:12]=2[OH:20])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:21]1[C:25]([C:26]2[CH:35]=[CH:34][C:29]([C:30]([NH:32][NH2:33])=[O:31])=[CH:28][CH:27]=2)=[N:24][N:23]=[N:22]1>CN(C)C=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([CH3:16])[N:14]=[C:13]([C:17](=[N:33][NH:32][C:30](=[O:31])[C:29]3[CH:34]=[CH:35][C:26]([C:25]4[NH:24][N:23]=[N:22][N:21]=4)=[CH:27][CH:28]=3)[CH3:18])[C:12]=2[OH:20])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

1-[5-(4-t-Butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethanone (0.404 mmol, 110 mg) and 4-(1-H-tetrazol-5-yl)benzhydrazide (0.404 mmol, 83 mg) synthesized in accordance with WO03/037328 were dissolved in dimethylformamide (5 mL) and stirred at 100° C. for 26 hours. The insolubles were filtered off and washed with methanol, and the filtrate was concentrated and separated by silica gel thin layer chromatography (chloroform/MeOH=4/1) to give the desired product as a yellow solid (25 mg, yield 13%).

Workup

filtrationThe insolubles were filtered off
washwashed with methanol
concentrationthe filtrate was concentrated
customseparated by silica gel thin layer chromatography (chloroform/MeOH=4/1)

Sources & evidence

ORD record: ord-56b9f90f045e41f7a2bdf3276b025a44
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318796B2

Reaction notes

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