Hydrochloric Acid → HCID 72359977, compound

HRID 2103841Notes

Reaction equation

HRID 2103841 reaction equation
[OH:1][C:2]1[C:3]([C:17](=[N:19][NH:20][C:21]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=2)=[O:22])[CH3:18])=[N:4][N:5]([CH3:16])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1.CO.[OH-].[Na+].Cl>O>[OH:1][C:2]1[C:3]([C:17](=[N:19][NH:20][C:21]([C:23]2[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=2)=[O:22])[CH3:18])=[N:4][N:5]([CH3:16])[C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86604741HCID 86604741, compound

Product 1

HCID 72359977HCID 72359977, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methyl 4-[(2-{1-[4-hydroxy-5-(4-isopropylphenyl)-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)-carbonyl]benzoate (0.037 mmol, 16.0 mg), methanol (3 mL) was added, and 1 M aqueous sodium hydroxide (5 eq., 0.184 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 (5 eq., 0.184 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 (6.8 mg, yield 44%).

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-726da542231345169d800c12b5f2629a
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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