Hydrochloric Acid → 6-[(2,2-Diethyl-3-sulfamoylpropyl)oxy]imidazo[1,2-b]pyridazine

HRID 465948Notes

Reaction equation

HRID 465948 reaction equation
[OH:1][CH2:2][C:3]([CH2:11][CH3:12])([CH2:9][CH3:10])[CH2:4][S:5]([NH2:8])(=[O:7])=[O:6].[H-].[Na+].Cl[C:16]1[CH:17]=[CH:18][C:19]2[N:20]([CH:22]=[CH:23][N:24]=2)[N:21]=1.Cl>CN(C=O)C>[CH2:9]([C:3]([CH2:11][CH3:12])([CH2:4][S:5](=[O:6])(=[O:7])[NH2:8])[CH2:2][O:1][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([CH:22]=[CH:23][N:24]=2)[N:21]=1)[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-HCID 105597653-Hydroxy-2,2-diethyl-1-propanesulfonamide

Product 1

HCID 98615706-[(2,2-Diethyl-3-sulfamoylpropyl)oxy]imidazo[1,2-b]pyridazineYield 62.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-hydroxy-2,2-diethyl-1-propanesulfonamide (1.0 g) in DMF (70 ml) was added sodium hydride (0.45 g), followed by heating at 70° C. for 30 minutes. The mixture to which 6-chloroimidazo [1,2-b]pyridazine (0.8 g) was added was heated for 5 hours. The reaction mixture was cooled, adjusted to pH 6.0 with 1N-hydrochloric acid and then concentrated. The residue was subjected to a silica gel column chlomatography, eluting with chloroform-methanol (10:1). The corresponding combined fractions were concentrated, thereby affording the above-identified compound (1.0 g).

Workup

  1. temperaturewas heated for 5 hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. washeluting with chloroform-methanol (10:1)
  5. concentrationThe corresponding combined fractions were concentrated

Sources & evidence

ORD record
ord-75cd9ce185c94ce4b88ff8c54438d8ef
Source dataset
uspto-grants-1992_10
Patent number
US05155108

Reaction notes

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