6-[3-(2-Chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazine → 6-{3-[2-(1H-benzimidazol-2-ylsulfanylmethyl)-3-methylpyridin-4-ylsulfanyl]propylsulfanyl}-3-nitroimidazo[1,2-b]pyridazine hydrochloride

HRID 1637630Notes

Reaction equation

HRID 1637630 reaction equation
[Cl:1][CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([S:10][CH2:11][CH2:12][CH2:13][S:14][C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([N+:24]([O-:26])=[O:25])=[CH:22][N:23]=3)[N:20]=2)[CH:6]=[CH:5][N:4]=1.[SH:27][C:28]1[NH:32][C:31]2[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=2[N:29]=1>C(O)(C)C>[ClH:1].[NH:29]1[C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=[C:28]1[S:27][CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([S:10][CH2:11][CH2:12][CH2:13][S:14][C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([N+:24]([O-:26])=[O:25])=[CH:22][N:23]=3)[N:20]=2)[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 187993836-[3-(2-Chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazineHCID 178527775HCID 178527775, compound

Product 1

HCID 187994206-{3-[2-(1H-benzimidazol-2-ylsulfanylmethyl)-3-methylpyridin-4-ylsulfanyl]propylsulfanyl}-3-nitroimidazo[1,2-b]pyridazine hydrochlorideYield 86.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 6-[3-(2-chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyrid-azine (0.39 g, 0.95 mmol) and 2-mercapto-1H-benzimidazole (160 mg, 1.05 mmol) in isopropanol (50 ml) is heated under reflux for 7 h. After cooling to room temperature, the precipitate is filtered off, washed with isopropanol and dried at 40° C. in vacuo. The title compound (0.46 g, 86%) is isolated as a beige solid. M.p. 200-207° C (dec.).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 7 h
  3. filtrationthe precipitate is filtered off
  4. washwashed with isopropanol
  5. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-2ea89ee7ae65441f99af13d320435e22
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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