p-Toluenesulfonic acid monohydrate → HCID 178497998, compound

HRID 555615Notes

Reaction equation

HRID 555615 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[C:15]([OH:16])=[C:14]([C:17](=O)[CH3:18])[C:13]([CH3:20])=[N:12]1.[CH3:21][O:22][C:23]([C:25]1[CH:34]=[CH:33][C:28]([C:29]([NH:31][NH2:32])=[O:30])=[CH:27][CH:26]=1)=[O:24].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[C:15](=[O:16])[C:14](=[C:17]([NH:32][NH:31][C:29](=[O:30])[C:28]2[CH:27]=[CH:26][C:25]([C:23]([O:22][CH3:21])=[O:24])=[CH:34][CH:33]=2)[CH3:18])[C:13]([CH3:20])=[N:12]1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 596004Methyl 4-(hydrazinecarbonyl)benzoateHCID 178466977HCID 178466977, compound

Product 1

HCID 178497998HCID 178497998, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2.0 mL of an isopropyl alcohol solution of 28.7 mg (0.11 mmol) of 1-(1-(quinolin-2-yl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl)-ethanone, 20.8 mg (0.11 mmol) of 4-methoxycarbonylbenzhydrazide and 6.1 mg (0.03 mmol) of p-toluenesulfonic acid monohydrate was refluxed with heating for 48 hours. After cooling, the precipitate was collected by filtration and washed with methanol and acetonitrile to obtain 14.9 mg of the desired product as a purple solid (yield 31%).

Workup

  1. temperaturewith heating for 48 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with methanol and acetonitrile

Sources & evidence

ORD record
ord-af6469b70bb241fbb811ffeaacb88fde
Source dataset
uspto-grants-2011_11
Patent number
US08053453B2

Reaction notes

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