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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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HRID 1662638 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11395974-(4-Piperidyl)pyridineHCID 27960291-Hydroxybenzotriazole hydrateHCID 21925457HCID 21925457, 화합물HCID 22619321HCID 22619321, 화합물

생성물 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-one수율 82.8%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6212Chloroform용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a7f821e6cd9c4bd4a30375b39d0dc9d2
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08030499B2

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