Hydrochloric Acid → HCID 72360116, compound

HRID 1881576Notes

Reaction equation

HRID 1881576 reaction equation
[OH:1][C:2]1[C:3]([C:18](=[N:20][NH:21][C:22]([C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=2)=[O:23])[CH3:19])=[N:4][N:5]([CH3:17])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=1.CO.[OH-].[Na+].Cl>O>[OH:1][C:2]1[C:3]([C:18](=[N:20][NH:21][C:22]([C:24]2[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:32][CH:33]=2)=[O:23])[CH3:19])=[N:4][N:5]([CH3:17])[C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH:14]([CH3:15])[CH3:16])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86604742HCID 86604742, compound

Product 1

HCID 72360116HCID 72360116, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methyl 4-[(2-{1-[4-hydroxy-5-(4-isobutylphenyl)-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]benzoate (0.129 mmol, 57.7 mg), methanol (2.5 mL) was added, and 1 M aqueous sodium hydroxide (5 eq., 0.643 mL) was added at room temperature. After 15 minutes of stirring at room temperature and 1.5 hours of stirring at 60° C., the reactor was cooled to room temperature, and 1 M hydrochloric acid (Seq., 0.643 mL) and water were added. The precipitated solid was recovered by filtration, washed with water and dried by means of a vacuum pump, and the residue was further purified by silica gel thin layer chromatography (chloroform/methanol=10/1). After addition of chloroform/n-hexane, the precipitated solid was dried to give the desired product as a yellow solid (25.6 mg, yield 46%).

Workup

  1. stirringof stirring at 60° C.
  2. temperaturethe reactor was cooled to room temperature
  3. filtrationThe precipitated solid was recovered by filtration
  4. washwashed with water
  5. customdried by means of a vacuum pump
  6. customthe residue was further purified by silica gel thin layer chromatography (chloroform/methanol=10/1)
  7. additionAfter addition of chloroform/n-hexane
  8. customthe precipitated solid was dried

Sources & evidence

ORD record
ord-07536d99034d474f92ff8b0aa0437c70
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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