Azane;hydrate → HCID 23028119, compound

HRID 1946441Notes

Reaction equation

HRID 1946441 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[N:6][N:5]2[C:12]=1[S:13]([N:16]=CN(CC(C)C)CC(C)C)(=[O:15])=[O:14].O.N>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[N:6][N:5]2[C:12]=1[S:13]([NH2:16])(=[O:14])=[O:15]

Participants

4

Reactant 2

HCID 12896473Azane;hydrateHCID 74015320HCID 74015320, compound

Product 1

HCID 23028119HCID 23028119, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N′-(2-Chloro-6-ethynylimidazo[1,2-b]pyridazin-3-ylsulfonyl)-N,N-diisobutylformamidine (792 mg, 2.00 mmol) was suspended in dioxane (10.0 mL), and 28% ammonia water (4.00 g, 65.8 mmol) was added dropwise to the suspension under stirring at room temperature. The mixture was stirred at room temperature for 3 days, then concentrated to remove ammonia, and adjusted to pH 1 with conc. hydrochloric acid. The reaction solution was diluted with water and extracted with ethyl acetate, and the extract was dehydrated over anhydrous magnesium sulfate and concentrated under reduced pressure. The residues were purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound as pale yellow crystals. The yield was 71 mg (13.8%).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 days
  2. concentrationconcentrated
  3. customto remove ammonia
  4. additionThe reaction solution was diluted with water
  5. extractionextracted with ethyl acetate
  6. concentrationconcentrated under reduced pressure
  7. customThe residues were purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-43a9d8136be948eab4c8d6ee3ab62399
Source dataset
uspto-grants-2013_03
Patent number
US08399381B2

Reaction notes

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