Hydrochloric Acid → HCID 72360050, compound

HRID 2103861Notes

Reaction equation

HRID 2103861 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[C:11]([OH:23])[C:10]([C:24](=[N:26][NH:27][C:28]([C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36]C)=[O:35])=[CH:32][CH:31]=2)=[O:29])[CH3:25])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Na+].Cl>O>[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]([C:19]([CH3:22])([CH3:20])[CH3:21])=[CH:17][CH:18]=2)=[C:11]([OH:23])[C:10]([C:24](=[N:26][NH:27][C:28]([C:30]2[CH:39]=[CH:38][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=2)=[O:29])[CH3:25])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86604750HCID 86604750, compound

Product 1

HCID 72360050HCID 72360050, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methyl 4-[(2-{1-[1-benzyl-5-(4-t-butylphenyl)-4-hydroxy-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]benzoate (0.045 mmol, 23.5 mg), methanol was added, and 1 M aqueous sodium hydroxide (0.224 mmol, 0.224 mL) was added at room temperature. After 30 minutes of stirring at room temperature and 1.5 hours of stirring at 60° C., the reactor was cooled to 0° C., and 1 M hydrochloric acid (0.224 mmol, 0.224 mL) and water were added. The precipitated solid was recovered by filtration, washed with water, dried by means of a vacuum pump and purified by silica gel thin layer chromatography (chloroform/methanol=10/1) to give the desired product as a yellow solid (15.8 mg, yield 69%).

Workup

  1. stirringof stirring at 60° C.
  2. temperaturethe reactor was cooled to 0° C.
  3. filtrationThe precipitated solid was recovered by filtration
  4. washwashed with water
  5. customdried by means of a vacuum pump
  6. custompurified by silica gel thin layer chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-33605f8895504caba3a00bab3cc63aa9
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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