Water → HCID 70273821, compound

HRID 1637641Notes

Reaction equation

HRID 1637641 reaction equation
Cl[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.N1C=CC=CC=1[N:33]1[CH:37]=[CH:36][N:35]=[C:34]1[SH:38].O>C(O)(C)C>[CH3:9][C:8]1[C:3]([CH:2]([S:38][C:34]2[NH:35][CH:36]=[CH:37][N:33]=2)[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)=[N:4][CH:5]=[CH:6][C:7]=1[S:10][CH2:11][CH2:12][CH2:13][S:14][C:15]1[CH:16]=[CH:17][C:18]2[N:19]([C:21]([N+:24]([O-:26])=[O:25])=[CH:22][N:23]=2)[N:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 187993836-[3-(2-Chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazineHCID 178527868HCID 178527868, compound

Product 1

HCID 70273821HCID 70273821, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2.3 g (5.6 mmol) of 6-[3-(2-chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazine and 1.0 g (5.6 mmol) of 1-pyridin-2-yl-1H-imidazole-2-thiol in 100 ml of isopropanol are heated under reflux for 2 h under a nitrogen atmosphere. The mixture is then cooled to room temperature, treated with 1 l of water and extracted with 4×200 ml of ethyl acetate. The organic extracts are washed with water, dried over magnesium sulfate and concentrated. The residue is purified by chromatography on silica gel (eluent: ethyl acetate/methanol/ammonia=19:1:0.6). The fractions of Rf =0.35 are concentrated and crystallized from methanol. 0.45 g of the title compound is isolated as a pale beige solid. M.p. 146-149° C.

Workup

  1. temperatureunder reflux for 2 h under a nitrogen atmosphere
  2. extractionextracted with 4×200 ml of ethyl acetate
  3. washThe organic extracts are washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography on silica gel (eluent: ethyl acetate/methanol/ammonia=19:1:0.6)
  7. concentrationThe fractions of Rf =0.35 are concentrated
  8. customcrystallized from methanol

Sources & evidence

ORD record
ord-0f074131e1304c1c847a879136e7047c
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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