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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
ノート
印刷プレビュー

反応式

HRID 1662638 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11395974-(4-Piperidyl)pyridineHCID 27960291-Hydroxybenzotriazole hydrateHCID 21925457HCID 21925457、化合物HCID 22619321HCID 22619321、化合物

生成物 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-one収率 82.8%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a7f821e6cd9c4bd4a30375b39d0dc9d2
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08030499B2

反応ノート

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