Triethylamine → N-(4-((2-(cyclopentanecarboxamido)pyridin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 520724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 520724
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[C:19](=[O:31])[N:20]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:21]([CH3:24])[C:22]=3[CH3:23])=[O:17])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.CCN(CC)CC.[CH:39]1([C:44](Cl)=[O:45])[CH2:43][CH2:42][CH2:41][CH2:40]1>C1COCC1.CN(C=O)C.C1COCC1.CCOC(C)=O>[CH:39]1([C:44]([NH:1][C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16]([C:18]4[C:19](=[O:31])[N:20]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:21]([CH3:24])[C:22]=4[CH3:23])=[O:17])=[CH:13][CH:14]=3)[CH:5]=[CH:4][N:3]=2)=[O:45])[CH2:43][CH2:42][CH2:41][CH2:40]1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 73053608N-(4-((2-aminopyridin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Produkt 1

HCID 73051530N-(4-((2-(cyclopentanecarboxamido)pyridin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of N-(4-((2-aminopyridin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (100 mg, 0.241 mmol) in THF/DMF (20 mL/1 mL) was added Et3N (0.06 mL, 0.481 mmol). The suspension was cooled to 0° C., a solution of cyclopentanecarbonyl chloride (64.0 mg, 0.481 mmol) in THF (5 mL) was added to the reaction mixture drop wise over 2 hours. The reaction was stirred at rt for 1.5 hours, then diluted with EtOAc (25 mL). The resulted mixture was washed with water (25 mL×3), followed by washing with brine (25 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/EtOAc/MeOH (v/v)=80/15/1) to give the title compound as a white solid (39 mg, 32%).

Aufarbeitung

  1. washThe resulted mixture was washed with water (25 mL×3)
  2. washby washing with brine (25 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (DCM/EtOAc/MeOH (v/v)=80/15/1)

Quellen und Nachweise

ORD-Eintrag
ord-c27a18b332bc4c7794267f959d1be51d
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09326975B2

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