Water → HCID 58046439, compound

HRID 2046420Notes

Reaction equation

HRID 2046420 reaction equation
BrC(Br)C([C:5]1[N:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]2=[N:7][CH:6]=1)=O.[C:15](OCC)(=[S:19])[C:16]([NH2:18])=O.[OH2:23].O1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>>[N:7]1[CH:6]=[C:5]([C:16]2[N:18]=[C:25]([C:26]([O:27][CH2:28][CH3:29])=[O:23])[S:19][CH:15]=2)[N:9]2[C:8]=1[CH:13]=[CH:12][CH:11]=[N:10]2

Participants

5

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 216137632-ethoxy-2-thioxoAcetamideHCID 58046377HCID 58046377, compound

Product 1

HCID 58046439HCID 58046439, compound

Conditions

Temperature
100 °C

Procedure

2,2-Dibromo-1-(imidazo[1,2-b]pyridazin-3-yl)ethanone (790 mg, 2.48 mmol) and ethyl thiooxamate (547 mg, 3.96 mmol) were dissolved in 1,4-dioxane (24.8 mL) and heated to 100° C. for 4 h. The solution was cooled to room temperature and water was added. The aqueous layer was extracted with ethyl acetate (×3). The organic layers were combined and dried with magnesium sulfate, filtered, and concentrated under reduced pressure to give the title compound as an orange solid. 1H NMR (500 MHz, CD3SOCD3) δ 8.79 (s, 1H); 8.77 (d, 1H); 8.33 (s, 1H); 8.30 (d, 1H); 7.39 (dd, 1H); 4.43 (q, 2H); 1.36 (t, 3H). LRMS (APCI) calc'd for (C12H10N4O2S) [M+H]+, 275.1. found 275.0.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate (×3)
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ea8403193834512b3959aa50a7787c0
Source dataset
uspto-grants-2013_11
Patent number
US08592425B2

Reaction notes

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