Potassium Carbonate → HCID 22272690, compound

HRID 1064865Notes

Reaction equation

HRID 1064865 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10]([CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(=[O:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]([NH:31][C:32]1[C:33]([S:41][CH3:42])=[N:34][C:35]([CH3:40])=[CH:36][C:37]=1[S:38][CH3:39])=[O:30]>CN(C=O)C.O>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10]([CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH2:28][C:29]([NH:31][C:32]2[C:33]([S:41][CH3:42])=[N:34][C:35]([CH3:40])=[CH:36][C:37]=2[S:38][CH3:39])=[O:30])[CH2:17][CH2:16]1)(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 222471492-Bromo-N-(6-methyl-2,4-bis(methylthio)pyridin-3-yl)acetamideHCID 22272600HCID 22272600, compound

Product 1

HCID 22272690HCID 22272690, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[2-(benzimidazol-2-ylsulfonyl)ethyl]piperazine (17 mg, 0.058 mmol) in DMF (0.1 ml) were added potassium carbonate (16.0 mg, 0.116 mmol) and 2-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide (18.6 mg, 0.058 mmol), and the mixture was stirred at room temperature for 6 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, 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 19.8 mg (yield 64%) of the desired compound as pale yellow oil. IR (neat) cm−1: 3345, 1672, 1565, 1420, 1124. 1H-NMR (CD3OD) δ: 2.43 (3H, s), 2.47 (3H, s), 2.48 (3H, s), 3.00 (2H, br. d, J=12.9 Hz), 3.12 (2H, t, J=10.7 Hz), 3.34 (2H, s), 3.58-3.78 (8H, m), 6.85 (1H, s), 7.12-7.18 (2H, m), 7.43-7.48 (2H, m).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution, 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-66f68127744c48cd91e7df1d995842d8
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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