Pyrazole → HCID 68531009, compound

HRID 386349Notes

Reaction equation

HRID 386349 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([C:14]([O:16][CH3:17])=[O:15])[NH:7][N:6]=1)=[O:4].N1C=CC=N1.[H-].[Na+].[C:25](Cl)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C=O>[C:25]([N:7]1[C:8]([C:14]([O:16][CH3:17])=[O:15])=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:5]([C:3]([O:2][CH3:1])=[O:4])=[N:6]1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 68527721HCID 68527721, compound

Product 1

HCID 68531009HCID 68531009, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The synthesis of this compound was done by tritylation of trimethyl-3,4,5-pyrazoletricarboxylate (1680 mg, 6.94 mmol) using a procedure similar to the one described in examples 2 and 3 for the synthesis of other tritylated pyrazole derivatives. The starting pyrazole reacted with sodium hydride (405 mg, 10.13 mmol) in dry dimethylformamide (80 mL) for 30 min at room temperature. Then, trityl chloride (1935 mg, 6.94 mmol) was added and the reaction mixture stirred overnight at room temperature. After removal of the solvent under vacuum, the resulting residue was washed with distilled water, n-hexane, and finally dried under vacuum to afford the title compound, as a white microcrystalline solid. Yield: 90% (3.034 g, 6.26 mmol).

Workup

  1. customThe synthesis of this compound
  2. customAfter removal of the solvent under vacuum
  3. washthe resulting residue was washed with distilled water, n-hexane
  4. customfinally dried under vacuum

Sources & evidence

ORD record
ord-40163fd5f924425a82e66549e68745a3
Source dataset
uspto-grants-2013_02
Patent number
US08372379B2

Reaction notes

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