Sodium hydride → 6-[(2,2-Dimethyl-3-sulfamoylpropyl)oxy]imidazo[1,2-b]pyridazine

HRID 465942Notes

Reaction equation

[OH:1][CH2:2][C:3]([CH3:10])([CH3:9])[CH2:4][S:5]([NH2:8])(=[O:7])=[O:6].[H-].[Na+].Cl[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([CH:20]=[CH:21][N:22]=2)[N:19]=1>CN(C=O)C>[CH3:9][C:3]([CH3:10])([CH2:4][S:5](=[O:7])(=[O:6])[NH2:8])[CH2:2][O:1][C:14]1[CH:15]=[CH:16][C:17]2[N:18]([CH:20]=[CH:21][N:22]=2)[N:19]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 3.5 g of 3-hydroxy-2,2-dimethyl-1-propanesulfonamide in 30 ml of DMF was added by portions 0.85 g of sodium hydride (60%, in oil)with stirring. To the mixture were added 3.18 g of 6-chloroimidazo[1,2-b]pyridazine and then 0.85 g of sodium hydride. The reaction solution was heated at 70° C. for 1.5 hours and then at 100° C. for an hour with stirring, and concentrated under reduced pressure. The residue was added into 100 ml of ice-water, extracted with ethyl acetate and tetrahydrofuran (1:1) (100 ml×4), dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was recrystallized from ethanol to obtain 5.18 g of the title compound.

Workup

stirringat 100° C. for an hour with stirring
concentrationconcentrated under reduced pressure
additionThe residue was added into 100 ml of ice-water
extractionextracted with ethyl acetate and tetrahydrofuran (1:1) (100 ml×4)
dry with materialdried over anhydrous magnesium sulfate
distillationdistilled under reduced pressure
customto remove the solvent
customThe residue was recrystallized from ethanol

Sources & evidence

ORD record: ord-ed2fc179561c4583b5761af94fece3fa
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05155108

Reaction notes

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