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

HRID 1740087노트

반응식

HRID 1740087 반응식
[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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 11263922Ethyl 2-(piperidin-4-yloxy)acetateHCID 154355041-(4-Cyanophenyl)-4-chlorocarbonyl-2-methyl-3-[4-(2-pyridyl)phenyl]-2H-pyrazol-5-one

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1ebe9ad5ed474f0098c9fd870433e11e
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968967

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