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4-(4-Piperidyl)pyridine → 5-chloro-3-(2-methoxyphenyl)-3-[2-oxo-2-(4-pyridin-4-yl piperidin-1-yl)ethyl]-1,3-dihydro-2H-indol-2-one

HRID 1662638
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Reaktionsgleichung

Reaktionsgleichung von HRID 1662638
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([CH2:20][C:21](O)=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19].[NH:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)[CH2:26][CH2:25]1.C1C=CC2N(O)N=NC=2C=1.O.C(Cl)CCl.Cl>C(Cl)(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])[CH2:20][C:21](=[O:22])[N:33]1[CH2:34][CH2:35][CH:30]([C:27]2[CH:26]=[CH:25][N:24]=[CH:29][CH:28]=2)[CH2:31][CH2:32]1
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Komponenten

7

Edukt 4

HCID 11395974-(4-Piperidyl)pyridineHCID 27960291-Hydroxybenzotriazole hydrateHCID 21925457HCID 21925457, VerbindungHCID 22619321HCID 22619321, Verbindung

Produkt 1

HCID 674277715-chloro-3-(2-methoxyphenyl)-3-[2-oxo-2-(4-pyridin-4-yl piperidin-1-yl)ethyl]-1,3-dihydro-2H-indol-2-oneAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 720 mg of [5-chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]acetic acid, which is the compound described in Preparation 1.1 of the brochure WO03/008407 and 350 mg of 4-piperidin-4-yl pyridine obtained in Step 51-1 in CHCl3 (15 ml) was added 500 mg of HOBt/H2O, stirred for 15 minutes, then, 500 mg of EDC/HCl was added. The solution was stirred for 11 hours, then, water was added and the resulting mixture was extracted with CHCl3. The organic layer was washed with water saturated brine, dried over Na2SO4, then, the drying agent was separated by filtration, and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (first time: silicagel 60; mobile phase: CHCl3/MeOH=9/1 to 5/1; second time: silica gel NH; mobile phase: CHCl3/MeOH=19/1) to obtain 850 mg of the title compound (colorless amorphous).

Aufarbeitung

  1. stirringThe solution was stirred for 11 hours
  2. extractionthe resulting mixture was extracted with CHCl3
  3. washThe organic layer was washed with water saturated brine
  4. dry with materialdried over Na2SO4
  5. customthe drying agent was separated by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (first time: silicagel 60; mobile phase: CHCl3/MeOH=9/1 to 5/1; second time: silica gel NH; mobile phase: CHCl3/MeOH=19/1)

Quellen und Nachweise

ORD-Eintrag
ord-a7f821e6cd9c4bd4a30375b39d0dc9d2
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08030499B2

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