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

HRID 655659노트

반응식

HRID 655659 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-49650c8cc2724bf6983143e4e0bf906f
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071600B2

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