Potassium Carbonate → 2-[4-[2-(imidazolo[4,5-b]pyridin-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide

HRID 1064871Notes

Reaction equation

HRID 1064871 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][N:45]([CH2:48][C:49]([NH:51][C:52]2[C:53]([S:61][CH3:62])=[N:54][C:55]([CH3:60])=[CH:56][C:57]=2[S:58][CH3:59])=[O:50])[CH2:44][CH2:43]1)(=O)=O>CN(C=O)C.O>[NH:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:10]=[C:2]1[S:1][CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][N:45]([CH2:48][C:49]([NH:51][C:52]2[C:53]([S:61][CH3:62])=[N:54][C:55]([CH3:60])=[CH:56][C:57]=2[S:58][CH3:59])=[O:50])[CH2:44][CH2:43]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 22272586HCID 22272586, compoundHCID 178527819HCID 178527819, compound

Product 1

HCID 222727162-[4-[2-(imidazolo[4,5-b]pyridin-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamideYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-mercaptoimidazolo[4,5-b]pyridine (38.1 mg, 0.252 mmol) in DMF (0.5 ml) were added 18-crown-6 (6.6 mg, 0.025 mmol) and potassium carbonate (63 mg, 0.454 mmol) and the mixture was stirred. Then to the mixture was dropped a solution of crude 2-[4-(2-methanesulfonyloxyethyl)piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide in DMF (1 ml) and stirred at 80° C. for 2 hours. The reaction mixture 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:methanol=10:1) to provide 51 mg (yield 40%) of the desired compound as colorless powdery crystals. IR (KBr) cm−1: 3140, 1688, 1600, 1564, 1485. 1H-NMR (CDCl3) δ: 2.38 (3H, s), 2.46 (3H, s), 2.49 (3H, s), 2.72-3.00 (10H, m), 3.29 (2H, s), 3.37 (2H, t, J=5.8 Hz), 6.63 (1H, s), 7.12 (1H, dd. J=7.8, 4.9 Hz), 7.82 (1H, d. J=7.8 Hz), 8.25 (1H, d. J=4.9 Hz), 8.49 (1H, br s).

Workup

  1. stirringstirred at 80° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution successively, dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-d5fe4e1cbfed47168fb406c3d23e7dfe
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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