m-Chloroperbenzoic acid → 2-[4-[2-(Benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-n-[2-methanesulfinyl-6-methyl-4-(methylthio)-3-pyridyl]-acetamide

HRID 1064863Notes

Reaction equation

HRID 1064863 reaction equation
C(O)(=O)/C=C\C(O)=[O:5].C(O)(=O)/C=C\C(O)=O.[N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[NH:19][C:18]=1[S:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36]([NH:38][C:39]2[C:40]([S:48][CH3:49])=[N:41][C:42]([CH3:47])=[CH:43][C:44]=2[S:45][CH3:46])=[O:37])[CH2:31][CH2:30]1.ClC1C=CC=C(C(OO)=O)C=1>C(Cl)(Cl)Cl.CO>[N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[NH:19][C:18]=1[S:26][CH2:27][CH2:28][N:29]1[CH2:30][CH2:31][N:32]([CH2:35][C:36]([NH:38][C:39]2[C:40]([S:48]([CH3:49])=[O:5])=[N:41][C:42]([CH3:47])=[CH:43][C:44]=2[S:45][CH3:46])=[O:37])[CH2:33][CH2:34]1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 865912422-[4-[2-(benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide dimaleate

Product 1

HCID 222726572-[4-[2-(Benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-n-[2-methanesulfinyl-6-methyl-4-(methylthio)-3-pyridyl]-acetamideYield 40.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

To a mixed solution of this amide (500 mg, 0.664 mmol) in chloroform (10 ml) and methanol (2 ml) was added m-chloroperbenzoic acid (213 mg, 1.23 mmol) with ice-cooling, and stirred at room temperature for 26 hours. The reaction solution was diluted with chloroform. The organic layer was washed with a saturated sodium bicarbonate solution 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=10:1) to provide 138 mg (yield 40%) of the desired compound as colorless amorphous. IR (neat) cm−1: 3424, 3155, 1695, 1571, 1481. 1H-NMR (d6-DMSO, 120° C.) δ: 2.51 (3H, s), 2.56 (3H, s), 2.73,(3H, s), 2.59-2.68 (6H, m), 2.77 (2H, t, J=7.1 Hz), 2.81-2.92 (2H, br s), 3.11 (1H, d, J=15.8 Hz), 3.17 (1H, d, J=15.8 Hz), 3.41 (2H, t, J=7.1 Hz), 7.07-7.13 (2H, m), 7.30 (1H, S), 7.38-7.44 (2H, m), 9.26 (1H, br s).

Workup

  1. temperaturecooling
  2. washThe organic layer was washed with a saturated sodium bicarbonate solution
  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=10:1)

Sources & evidence

ORD record
ord-7f21cec324cc41cf98a5beb9fa40b802
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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