Dichloromethane → 5-Benzyloxymethyl-4-oxo-4,5-dihydroimidazo[4,5-d]pyridazine-1-sulfonic acid dimethylamide

HRID 501398Notes

Reaction equation

HRID 501398 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:14])[S:10](Cl)(=[O:12])=[O:11].ClCCl.[CH2:18]([O:25][CH2:26][N:27]1[C:32](=[O:33])[C:31]2=[N:34][CH:35]=[N:36][C:30]2=[CH:29][NH:28]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:8][N:9]([CH3:14])[S:10]([N:36]1[C:30]2[CH:29]=[N:28][N:27]([CH2:26][O:25][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:32](=[O:33])[C:31]=2[N:34]=[CH:35]1)(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 178515257HCID 178515257, compound

Product 1

HCID 594241055-Benzyloxymethyl-4-oxo-4,5-dihydroimidazo[4,5-d]pyridazine-1-sulfonic acid dimethylamideYield 66.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.08 g of triethylamine, 2.80 g of N,N-dimethyl sulfamoyl chloride, and 0.22 g of 4-dimethylaminopyridine were added to 50 ml of a dichloromethane solution of 3.04 g of 5-benzyloxymethylimidazo[4,5-d]pyridazin-4-one [CAS NO. 82137-50-6] (R. Paul Gagnier, Michael J. Halat, and Brian A. Otter Journal of Heterocyclic Chemistry, 21, p 481, 1984), and the mixture was heated under reflux for 4 hours. 250 ml of ethyl acetate was added to the solution, and the mixture was washed successively with 50 ml of an aqueous solution of 1N hydrochloric acid, 50 ml of a saturated sodium bicarbonate solution, and 50 ml of a saturated sodium chloride solution. The mixture was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 2.86 g of the title compound was obtained from the fraction eluted with hexane-ethyl acetate (2:3).

Workup

  1. temperatureunder reflux for 4 hours
  2. washthe mixture was washed successively with 50 ml of an aqueous solution of 1N hydrochloric acid, 50 ml of a saturated sodium bicarbonate solution, and 50 ml of a saturated sodium chloride solution
  3. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4bdb1ca9e63343f4a2535bd003ac6f0d
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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