Sodium Iodide → methyl 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazole-3-carboxylate

HRID 655659ノート

反応式

HRID 655659 の反応式
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[N:10]([CH3:11])[N:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=1.Cl.[S:17]1[CH:21]=[CH:20][C:19]2[C:22]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:23][CH:24]=[CH:25][C:18]1=2.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.CN(C=O)C>[S:17]1[CH:21]=[CH:20][C:19]2[C:22]([N:26]3[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][O:5][C:6]4[N:10]([CH3:11])[N:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=4)[CH2:28][CH2:27]3)=[CH:23][CH:24]=[CH:25][C:18]1=2

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 574825411-(1-Benzothiophen-4-yl)piperazine hydrochlorideHCID 57482559methyl 5-(3-chloropropoxy)-1-methyl-1H-pyrazole-3-carboxylate

生成物 1

HCID 16044810methyl 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazole-3-carboxylate収率 71.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Methyl 5-(3-chloropropoxy)-1-methyl-1H-pyrazole-3-carboxylate (1.17 g, 5.0 mmol), 1-benzo[b]thiophen-4-yl piperazine hydrochloride (1.35 g, 5.3 mmol), potassium carbonate (1.74, 12.6 mmol) and sodium iodide (0.75 g, 5.0 mmol) were added to DMF (12 ml), and the mixture was stirred at 80° C. for 3 hours. The reaction solution was cooled to room temperature and water was added thereto, and then, extracted with ethyl acetate. The organic phase was washed with water and dried over magnesium sulfate. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:3→dichloromethane:methanol=100:3). The purified product was concentrated under reduced pressure to obtain a light yellow oily substance (1.97 g). The oily substance was allowed to stand still at room temperature to obtain a solid substance, which was washed with diisopropyl ether and dried to obtain methyl 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazole-3-carboxylate (1.49 g).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe reaction solution was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:3→dichloromethane:methanol=100:3)
  7. concentrationThe purified product was concentrated under reduced pressure
  8. customto obtain a light yellow oily substance (1.97 g)
  9. customto stand still at room temperature
  10. customto obtain a solid substance, which
  11. washwas washed with diisopropyl ether
  12. customdried

出典と根拠

ORDレコード
ord-49650c8cc2724bf6983143e4e0bf906f
出典データセット
uspto-grants-2011_12
特許番号
US08071600B2

反応ノート

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