Phenyl isocyanate → N-[3-(imidazo[1,2-b]pyridazin-6-yloxy)phenyl]-N'-phenylurea

HRID 1663771Notes

Reaction equation

HRID 1663771 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([O:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14])=[N:5]2.C(N(CC)CC)C.[C:25]1([N:31]=[C:32]=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([O:10][C:11]1[CH:12]=[C:13]([NH:14][C:32]([NH:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:33])[CH:15]=[CH:16][CH:17]=1)=[N:5]2

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 574410563-(Imidazo[1,2-b]pyridazin-6-yloxy)aniline

Product 1

HCID 57505525N-[3-(imidazo[1,2-b]pyridazin-6-yloxy)phenyl]-N'-phenylureaYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(imidazo[1,2-b]pyridazin-6-yloxy)aniline (181 mg, 0.80 mmol) and triethylamine (0.011 mL, 0.08 mmol) in tetrahydrofuran (10 mL) was added phenyl isocyanate (0.104 mL, 0.96 mmol), and the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate/methanol=100/0→90/10) and precipitated from ethyl acetate to give the title compound (196 mg, 71%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by NH silica gel column chromatography (ethyl acetate/methanol=100/0→90/10)
  3. customprecipitated from ethyl acetate

Sources & evidence

ORD record
ord-b3600db0fa984732bf55c40cee8ea7b7
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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