Hydrochloric Acid → 5-[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]-2-thiophenecarboxylic acid

HRID 2103863Notes

Reaction equation

HRID 2103863 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](=[N:19][NH:20][C:21]([C:23]3[S:27][C:26]([C:28]([O:30]C)=[O:29])=[CH:25][CH:24]=3)=[O:22])[CH3:18])[C:12]=2[OH:32])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[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:19][NH:20][C:21]([C:23]3[S:27][C:26]([C:28]([OH:30])=[O:29])=[CH:25][CH:24]=3)=[O:22])[CH3:18])[C:12]=2[OH:32])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 72359930methyl 5-[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]-2-thiophenecarboxylate

Product 1

HCID 723599415-[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]-2-thiophenecarboxylic acidYield 40.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]-2-thiophenecarboxylate (16.0 mg, 0.035 mmol) in methanol (1.5 mL) was stirred with 1 M aqueous sodium hydroxide (176 μL, 0.176 mmol) at room temperature for 17 hours. After the stirring, 1 M hydrochloric acid (176 μL, 0.176 mmol) was added, and the precipitated solid was recovered by filtration to give 6.2 mg of the desired product as yellow crystals (yield 40%).

Workup

  1. filtrationthe precipitated solid was recovered by filtration

Sources & evidence

ORD record
ord-99e0878871a9416abc7f3fe62c96916c
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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