Water → HCID 178431910, compound

HRID 1637636Notes

Reaction equation

HRID 1637636 reaction equation
ClC[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.O.[NH2:28][C:29]1[N:34]=[C:33]([SH:35])[NH:32][C:31](=[O:36])[CH:30]=1.[C:37](=O)([O-])[O-].[Na+].[Na+].O>C(O)(C)C>[NH2:28][C:29]1[N:34]=[C:33]([SH:35]([C:3]2[C:8]([CH3:9])=[C:7]([S:10][CH2:11][CH2:12][CH2:13][S:14][C:15]3[CH:16]=[CH:17][C:18]4[N:19]([C:21]([N+:24]([O-:26])=[O:25])=[CH:22][N:23]=4)[N:20]=3)[CH:6]=[CH:5][N:4]=2)[CH3:37])[NH:32][C:31](=[O:36])[CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 187993836-[3-(2-Chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazineHCID 178507964HCID 178507964, compound

Product 1

HCID 178431910HCID 178431910, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 0.7 g (1.7 mmol) of 6-[3-(2-chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazine, 0.275 g (1.7 mmol) of 6-amino-2-mercapto-3H-pyrimidin-4-one monohydrate and 0.18 g (1.7 mmol) of sodium carbonate in 20 ml of isopropanol is heated under reflux for 2.5 h. The suspension is then added to 250 ml of water and stirred at room temperature for 30 min. The precipitate is filtered off, washed with water, dried in a high vacuum and suspended in hot methanol. After filtering and drying again, 0.83 g (94%) of the title compound is isolated as a pale beige solid. M.p.: 244-246° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2.5 h
  3. filtrationThe precipitate is filtered off
  4. washwashed with water
  5. customdried in a high vacuum
  6. filtrationAfter filtering
  7. customdrying again

Sources & evidence

ORD record
ord-c1542947c9de4adb95a5c205df4c2d1f
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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