Triethylamine → N-[3-(imidazo[1,2-b]pyridazin-6-yloxy)phenyl]-N'-[3-(trifluoromethyl)phenyl]urea

HRID 1667958Notes

Reaction equation

HRID 1667958 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.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:28]=[C:29]([N:33]=[C:34]=[O:35])[CH:30]=[CH:31][CH:32]=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:34]([NH:33][C:29]3[CH:30]=[CH:31][CH:32]=[C:27]([C:26]([F:25])([F:36])[F:37])[CH:28]=3)=[O:35])[CH:15]=[CH:16][CH:17]=1)=[N:5]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 574410563-(Imidazo[1,2-b]pyridazin-6-yloxy)aniline

Product 1

HCID 57505526N-[3-(imidazo[1,2-b]pyridazin-6-yloxy)phenyl]-N'-[3-(trifluoromethyl)phenyl]ureaYield 62%

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 (0.040 mL, 0.29 mmol) in tetrahydrofuran (10 mL) was added 3-(trifluoromethyl)phenyl isocyanate (0.154 mL, 1.12 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 silica gel column chromatography (ethyl acetate/methanol=100/0→90/10) and precipitated from methanol to give the title compound (205 mg, 62%) as a white powder.

Workup

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

Sources & evidence

ORD record
ord-e9299e9ee10242efbf92b7483cebd45c
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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