Sodium Iodide → N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-2-nitro-N-{2-[4-(pyridin-3-ylmethoxy)piperidin-1-yl]ethyl}benzenesulfonamide

HRID 69018ノート

反応式

HRID 69018 の反応式
[I-].[Na+].[CH3:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH2:17][N:18]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[N+:35]([O-:37])=[O:36])(=[O:28])=[O:27])[CH2:19][CH2:20]OS(C)(=O)=O)=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]1=[O:38].[N:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][O:46][CH:47]2[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)[CH:40]=1.C(N(C(C)C)C(C)C)C>C(#N)C>[CH3:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:19][CH2:20][N:50]3[CH2:51][CH2:52][CH:47]([O:46][CH2:45][C:41]4[CH:40]=[N:39][CH:44]=[CH:43][CH:42]=4)[CH2:48][CH2:49]3)[S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[N+:35]([O-:37])=[O:36])(=[O:27])=[O:28])=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]1=[O:38]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 207352943-((4-Piperidinyloxy)methyl)pyridineHCID 86762687Methanesulfonic acid 2-[[3-(1-methyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)propyl]-(2-nitro-benzenesulfonyl)amino]-ethyl ester

生成物 1

HCID 86762686N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-2-nitro-N-{2-[4-(pyridin-3-ylmethoxy)piperidin-1-yl]ethyl}benzenesulfonamide収率 67.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

Sodium iodide (2.93 g) was added to a acetonitrile solution (20 ml) of methanesulfonic acid 2-[[3-(1-methyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)propyl]-(2-nitro-benzenesulfonyl)amino]-ethyl ester (4.37 g), and stirred at 60° C. for 1 hours. The reaction mixture was cooled to room temperature. 4-(pyridin-3-ylmethoxy)piperidine (1.87 g) and N-ethyl diisopropylamine (4.23 ml) were then added to the reaction mixture and stirred at 60° C. for 5 hours. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. Water was added to the residue, and extraction with dichloromethane was performed. The organic layer was washed with water, and a saturated sodium chloride aqueous solution, in this order. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0→10:1). The purified product was concentrated under reduced pressure to give the title compound (3.48 g) as a yellow solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringstirred at 60° C. for 5 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. additionWater was added to the residue, and extraction with dichloromethane
  6. washThe organic layer was washed with water
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0→10:1)
  10. concentrationThe purified product was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-adec4ad213f84804b11f908c30e5982f
出典データセット
uspto-grants-2014_09
特許番号
US08822453B2

反応ノート

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