Tetrahydrofuran → 3-(4-t-Butylphenyl)-4-{[4-(ethoxycarbonylmethyloxy)-1-piperidinyl]carbonyl}-1-(4-cyanophenyl)-2-methyl-2H-pyrazol-5-one

HRID 1740079Notes

Reaction equation

HRID 1740079 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH3:28])[N:13]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)[C:14](=[O:19])[C:15]=2[C:16](Cl)=[O:17])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.O1CCCC1.[NH:41]1[CH2:46][CH2:45][CH:44]([O:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH2:43][CH2:42]1>CN(C)C=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH3:28])[N:13]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)[C:14](=[O:19])[C:15]=2[C:16]([N:41]2[CH2:42][CH2:43][CH:44]([O:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH2:45][CH2:46]2)=[O:17])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 11263922Ethyl 2-(piperidin-4-yloxy)acetateHCID 154355013-(4-t-Butylphenyl)-4-chlorocarbonyl-1-(4-cyanophenyl)-2-methyl-2H-pyrazol-5-one

Product 1

HCID 154355023-(4-t-Butylphenyl)-4-{[4-(ethoxycarbonylmethyloxy)-1-piperidinyl]carbonyl}-1-(4-cyanophenyl)-2-methyl-2H-pyrazol-5-oneYield 28.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.5 g of 3-(4-t-butylphenyl)-4-chlorocarbonyl-1-(4-cyanophenyl)-2-methyl-2H-pyrazol-5-one, 1.8 g of triethylamine, 50 ml of tetrahydrofuran, 20 ml of N,N-dimethylformamide and 2.38 g of ethyl 4-piperidinoxyacetate was stirred at room temperature for 20 hours. The reaction solution was evaporated under reduced pressure, and after addition of water, the resulting residue was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride successively and dried over sodium sulfate. The insolubles were filtered off, and then the solvent was removed by evaporation. The resulting residue was purified by silica gel chromatography (eluent; ethyl acetate/chloroform=1:1) to give 1.38 g of the title compound as a colorless amorphous solid.

Workup

  1. customThe reaction solution was evaporated under reduced pressure
  2. additionafter addition of water
  3. extractionthe resulting residue was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride successively
  5. dry with materialdried over sodium sulfate
  6. filtrationThe insolubles were filtered off
  7. customthe solvent was removed by evaporation
  8. customThe resulting residue was purified by silica gel chromatography (eluent; ethyl acetate/chloroform=1:1)

Sources & evidence

ORD record
ord-2c482125334644869aa6236c5ad71c66
Source dataset
uspto-grants-1999_10
Patent number
US05968967

Reaction notes

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