Water → S-{3-methyl-4-[3-(3-nitroimidazo[1,2-b]pyridazin-6-ylsulfanyl)propylsulfanyl]-pyridin-2-ylmethyl} thioacetate

HRID 1637635Notes

Reaction equation

HRID 1637635 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:13][C:14]1[C:19]([CH3:20])=[C:18]([S:21][CH2:22][CH2:23][CH2:24][S:25][C:26]2[CH:27]=[CH:28][C:29]3[N:30]([C:32]([N+:35]([O-:37])=[O:36])=[CH:33][N:34]=3)[N:31]=2)[CH:17]=[CH:16][N:15]=1.O>CN(C)C=O>[C:1]([S:3][CH2:13][C:14]1[C:19]([CH3:20])=[C:18]([S:21][CH2:22][CH2:23][CH2:24][S:25][C:26]2[CH:27]=[CH:28][C:29]3[N:30]([C:32]([N+:35]([O-:37])=[O:36])=[CH:33][N:34]=3)[N:31]=2)[CH:17]=[CH:16][N:15]=1)(=[O:4])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 187993836-[3-(2-Chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazineHCID 23670855Potassium ethanethioate

Product 1

HCID 57117835S-{3-methyl-4-[3-(3-nitroimidazo[1,2-b]pyridazin-6-ylsulfanyl)propylsulfanyl]-pyridin-2-ylmethyl} thioacetateYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of potassium thioacetate (0.44 g, 3.75 mmol) and potassium carbonate (0.87 g, 6.25 mmol) in 10 ml of dimethylformamide is stirred at room temperature for 30 min and then treated with a solution of 1.03 g (2.5 mmol) of 6-[3-(2-chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazine in 10 ml of dimethylformamide. The suspension is stirred at room temperature for a further 18 h. Water (100 ml) is then added, and the mixture is cooled to 0° C. and filtered. After drying the solid in vacuo at 40° C., it is additionally suspended in hot diisopropyl ether. After cooling to room temperature, the solid is again filtered and dried. 1.02 g (98%) of the title compound are isolated as a pale beige solid. M.p.: 138-140° C.

Workup

  1. stirringThe suspension is stirred at room temperature for a further 18 h
  2. temperaturethe mixture is cooled to 0° C.
  3. filtrationfiltered
  4. customAfter drying the solid in vacuo at 40° C.
  5. temperatureAfter cooling to room temperature
  6. filtrationthe solid is again filtered
  7. customdried

Sources & evidence

ORD record
ord-f62b2d473d984cfcadf6804952986b41
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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