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Potassium Carbonate → 2-[4-[2-(benzimidazol-2ylsulfinyl)ethyl]piperazin-1-yl]-N-[2-(methanesulfinyl)-6methyl-4-(methylthio)-3-pyridyl] acetamide

HRID 1064867
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HRID 1064867 반응식
Br[CH2:2][C:3]([NH:5][C:6]1[C:7]([S:15]([CH3:17])=[O:16])=[N:8][C:9]([CH3:14])=[CH:10][C:11]=1[S:12][CH3:13])=[O:4].[N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[NH:20][C:19]=1[S:27]([CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:28].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[NH:20][C:19]=1[S:27]([CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][N:34]([CH2:2][C:3]([NH:5][C:6]2[C:7]([S:15]([CH3:17])=[O:16])=[N:8][C:9]([CH3:14])=[CH:10][C:11]=2[S:12][CH3:13])=[O:4])[CH2:33][CH2:32]1)=[O:28]
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 222726272-bromo-N-[2(methanesulfinyl)-6-methyl-4-(methylthio)-3-pyridyl]acetamideHCID 22272679HCID 22272679, 화합물

생성물 1

HCID 222725852-[4-[2-(benzimidazol-2ylsulfinyl)ethyl]piperazin-1-yl]-N-[2-(methanesulfinyl)-6methyl-4-(methylthio)-3-pyridyl] acetamide수율 49.6%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6228Dimethylformamide용매

실험 절차

To a solution of this sulfoxide (21.4 mg, 0.063 mmol) in DMF (1 ml) were added 1-[2-(benzimidazol-2-ylsulfinyl)ethyl]piperazine (17.6 mg, 0.063 mmol) obtained in Example 146 and potassium carbonate (17.5 mg, 0.127 mmol), and stirred for 12 hours. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:sat. ammonia methanol=5:1) to provide 16.7 mg (yield 49%) of the desired compound as pale yellow oil. IR (KBr) cm−1: 3190, 2993, 1674, 1571, 1484. 1H-NMR (CD3OD) δ: 2.15-2.65 (14H, m), 2.63-2.84 (5H, m), 2.89 (2H, s), 3.34 (1H, dt, J=12.0, 6.0 Hz), 3.43 (1H, dt, J=12.0, 6.0 Hz), 7.22 (1H, s), 7.23-7.28 (2H, m), 7.55-7.59 (2H, m).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution successively, dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:sat. ammonia methanol=5:1)

출처 및 근거

ORD 기록
ord-a185c7c903b14a06a6ae28679af2043a
출처 데이터셋
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06969711B2

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