Hydrochloric Acid → 2-Chloro-6-cyclopropylimidazo[1,2-b]pyridazine-3-sulfonamide

HRID 1946439Notes

Reaction equation

HRID 1946439 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([CH:10]3[CH2:12][CH2:11]3)=[N:6][N:5]2[C:13]=1[S:14]([N:17]=CN(CC(C)C)CC(C)C)(=[O:16])=[O:15].Cl>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([CH:10]3[CH2:12][CH2:11]3)=[N:6][N:5]2[C:13]=1[S:14]([NH2:17])(=[O:15])=[O:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68535377HCID 68535377, compound

Product 1

HCID 230281432-Chloro-6-cyclopropylimidazo[1,2-b]pyridazine-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

N′-(2-Chloro-6-cyclopropylimidazo[1,2-b]pyridazin-3-ylsulfonyl)-N,N-diisobutylformamidine (0.93 g, 2.26 mmol) was dissolved in dioxane (9.00 mL), and 36% conc. hydrochloric acid (9.0 mL, 107 mmol) was added dropwise to the solution under stirring at 100° C. The mixture was stirred for 15 hours at 100 to 105° C., then left and cooled to room temperature and concentrated under reduced pressure until crystals occurred. Water (30.0 mL) was poured into the residues, and the crystals were completely precipitated, then filtered, washed with water and washed with methanol, to give the title compound as white crystals. The yield was 0.31 g (50.4%).

Workup

  1. stirringThe mixture was stirred for 15 hours at 100 to 105° C.
  2. waitleft
  3. temperaturecooled to room temperature
  4. concentrationconcentrated under reduced pressure until crystals
  5. additionWater (30.0 mL) was poured into the residues
  6. customthe crystals were completely precipitated
  7. filtrationfiltered
  8. washwashed with water
  9. washwashed with methanol

Sources & evidence

ORD record
ord-8e2aaca8457140178da5218a8888ec67
Source dataset
uspto-grants-2013_03
Patent number
US08399381B2

Reaction notes

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