K-604 → HCID 22272607, compound

HRID 1064864Notes

Reaction equation

HRID 1064864 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][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]([NH:22][C:23]2[C:24]([S:32][CH3:33])=[N:25][C:26]([CH3:31])=[CH:27][C:28]=2[S:29][CH3:30])=[O:21])[CH2:15][CH2:14]1.B1([O-])O[O:35]1.O.O.O.O.[Na+]>C(O)(=O)C>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([CH2:19][C:20]([NH:22][C:23]2[C:24]([S:32][CH3:33])=[N:25][C:26]([CH3:31])=[CH:27][C:28]=2[S:29]([CH3:30])=[O:35])=[O:21])[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 9892288K-604HCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 22272607HCID 22272607, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 2-[4-[2-(benzimidazol-2ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide (1.00 g, 1.99 mmol) in acetic acid (20 ml) was dropped a solution of sodium perborate tetrahydrate (321 mg, 2.09 mmol) in acetic acid (30 ml), and the mixture was stirred for 3 hours. The reaction solution was concentrated in vacuo and the resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:sat. ammonia methanol 15:1) to provide 73 mg (yield 7%) of 2-[4-[2-(benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[4-methanesulfinyl-6-methyl-2-(methylthio)-3-pyridyl]acetamide as pale yellow oil. IR (KBr) cm−1: 3375, 2496, 1672, 1553, 1122. 1H-NMR (CD3OD) δ: 2.45 (3H, s), 2.51 (3H, s), 2.52-2.64 (8H,m), 2.70 (2H, t, J=6.8 Hz), 2.72 (3H, s), 3.04 (1H, d, J=16.1 Hz), 3.13 (1H, d, J=16.1 Hz), 3.30 (2H, t, J=6.8 Hz), 7.04-7.10 (2H, m), 7.32 (1H, s), 7.33-7.38 (2H, m), 7.78 (1H, s).

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. customthe resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:sat. ammonia methanol 15:1)

Sources & evidence

ORD record
ord-711d0684d3194de4863867deb53bf143
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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