Water → HCID 22024686, compound

HRID 501025Notes

Reaction equation

HRID 501025 reaction equation
C([N:3]([CH2:6]C)CC)C.[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].C1(C2C(C3C=CC=CC=3)=C(N=[N+]=[N-])PC=2)C=CC=CC=1.[CH3:33][C:34]1[CH:39]=[C:38]([CH3:40])[CH:37]=[CH:36][C:35]=1[C:41]1[C:42]2[N:43]([C:48](C(O)=O)=[C:49]([CH2:51][CH3:52])[N:50]=2)[N:44]=[C:45]([CH3:47])[CH:46]=1.[OH2:56]>C1(C)C=CC=CC=1>[CH3:33][C:34]1[CH:39]=[C:38]([CH3:40])[CH:37]=[CH:36][C:35]=1[C:41]1[C:42]2[N:43]([C:48]([NH:3][C:6](=[O:56])[O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[C:49]([CH2:51][CH3:52])[N:50]=2)[N:44]=[C:45]([CH3:47])[CH:46]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6386tert-ButanolHCID 8471TriethylamineHCID 22024418HCID 22024418, compoundHCID 54443253HCID 54443253, compound

Product 1

HCID 22024686HCID 22024686, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

Triethylamine (20 mL), tert-butyl alcohol (30 mL) and diphenylphospholylazide (1.95 mL, 9.05 mmol) were added to a solution of the resulting 8-(2,4-dimethylphenyl)-2-ethyl-6-methylimidazo[1,2-b]pyridazine-3-carboxylic acid (2.8 g, 9.05 mmol) in toluene (40 mL), and the mixture was heated at 140° C. for 6 hours. Water was added thereto, which was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and evaporated, to give tert-butyl N-[8-(2,4-dimethylphenyl)-2-ethyl-6-methylimidazo[1,2-b]pyridazin-3-yl]carbamate as a crude compound.

Workup

  1. extractionwhich was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-d54dea0144f947c6a3c8603f46df61e2
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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