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

HRID 1064867Notes

Reaction equation

HRID 1064867 reaction equation
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]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22272627HCID 22272627, compoundHCID 22272679HCID 22272679, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-a185c7c903b14a06a6ae28679af2043a
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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