Triethylamine → 6-{3-[3-Methyl-2-(pyrimidin-2-ylsulfanylmethyl)-pyridin-4-ylsulfanyl]propyisulfanyl)3-nitro-imidazo[1,2-b]pyridazine

HRID 1637632Notes

Reaction equation

HRID 1637632 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.[SH:27][C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C(N(CC)CC)C>C(O)(C)C>[CH3:9][C:8]1[C:3]([CH2:2][S:27][C:28]2[N:33]=[CH:32][CH:31]=[CH:30][N:29]=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 8471TriethylamineHCID 187993836-[3-(2-Chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazineHCID 178418793HCID 178418793, compound

Product 1

HCID 702725486-{3-[3-Methyl-2-(pyrimidin-2-ylsulfanylmethyl)-pyridin-4-ylsulfanyl]propyisulfanyl)3-nitro-imidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 6-[3-(2-chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazine (1.23 g, 3.0 mmol), 2-mercaptopyrimidine (330 mg, 2.9 mmol) and triethylamine (335 mg, 3.3 mmol) in isopropanol (100 ml) is heated under reflux for 4.5 h. After cooling, the suspension is stirred at room temperature for a further 18 h and then at 0° C. for 0.5 h. The precipitate is filtered off, washed with isopropanol and dried at 40° C. in vacuo. The crystalline solid is then suspended in water (50 ml) and sodium carbonate solution (10 ml). After filtration and drying in vacuo at 40° C., the title compound is isolated as a pale beige solid. Yield 1.40 g (93%), m.p. 143-147° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4.5 h
  3. temperatureAfter cooling
  4. waitat 0° C. for 0.5 h
  5. filtrationThe precipitate is filtered off
  6. washwashed with isopropanol
  7. customdried at 40° C. in vacuo
  8. filtrationAfter filtration
  9. customdrying in vacuo at 40° C.

Sources & evidence

ORD record
ord-c1ba600103584a7e863b1d84bb339ac1
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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