Triethylamine → 4-{[4-(Carboxymethyloxy)-1-piperidinyl]carbonyl}-1-(4-cyanophenyl)-2-methyl-3-[4-(2-pyridyl)phenyl]-2H-pyrazol-5-one

HRID 1740087Notes

Reaction equation

HRID 1740087 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[C:12]([C:15](Cl)=[O:16])=[C:11]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[CH:20][CH:19]=3)[N:10]2[CH3:30])=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.[NH:38]1[CH2:43][CH2:42][CH:41]([O:44][CH2:45][C:46]([O:48]CC)=[O:47])[CH2:40][CH2:39]1>O1CCCC1>[C:46]([CH2:45][O:44][CH:41]1[CH2:40][CH2:39][N:38]([C:15]([C:12]2[C:13](=[O:14])[N:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[N:10]([CH3:30])[C:11]=2[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:20][CH:19]=2)=[O:16])[CH2:43][CH2:42]1)([OH:48])=[O:47]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11263922Ethyl 2-(piperidin-4-yloxy)acetateHCID 15435504HCID 15435504, compound

Product 1

HCID 154355054-{[4-(Carboxymethyloxy)-1-piperidinyl]carbonyl}-1-(4-cyanophenyl)-2-methyl-3-[4-(2-pyridyl)phenyl]-2H-pyrazol-5-oneYield 11.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.62 g of 1-(4-cyanophenyl)-4-chlorocarbonyl-2-methyl-3-[4-(2-pyridyl)phenyl]-2H-pyrazol-5-one, 2.04 g of triethylamine, 20 ml of tetrahydrofuran and 1.35 g of ethyl 4-piperidinoxyacetate was stirred at room temperature for 16 hours. The reaction solution was evaporated under reduced pressure, and the resulting residue was extracted with chloroform. The organic layer was washed with saturated aqueous sodium chloride and dried over sodium sulfate. The insolubles were filtered off, and the solvent was removed by evaporation. The resulting residue was crystallized in chloroform-methanol-ethyl acetate to give 250 mg of the title compound as pale yellow crystals. The mother liquor was evaporated under reduced pressure, and the resulting residue was purified by silica gel chromatography (eluent;ethyl acetate:methanol 9:1). The resulting crude crystals were recrystallized in chloroform-methanol-ethyl acetate to give 601 mg of the title compound as pale pink crystals.

Workup

  1. customThe reaction solution was evaporated under reduced pressure
  2. extractionthe resulting residue was extracted with chloroform
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationThe insolubles were filtered off
  6. customthe solvent was removed by evaporation
  7. customThe resulting residue was crystallized in chloroform-methanol-ethyl acetate

Sources & evidence

ORD record
ord-1ebe9ad5ed474f0098c9fd870433e11e
Source dataset
uspto-grants-1999_10
Patent number
US05968967

Reaction notes

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