Triethylamine → N-[3-(imidazo[1,2-b]pyridazin-6-yloxy)phenyl]-N'-[4-(trifluoromethyl)phenyl]urea

HRID 1667959Notes

Reaction equation

HRID 1667959 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:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=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:30]3[CH:29]=[CH:28][C:27]([C:26]([F:25])([F:36])[F:37])=[CH:32][CH:31]=3)=[O:35])[CH:15]=[CH:16][CH:17]=1)=[N:5]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 574410563-(Imidazo[1,2-b]pyridazin-6-yloxy)aniline

Product 1

HCID 57505527N-[3-(imidazo[1,2-b]pyridazin-6-yloxy)phenyl]-N'-[4-(trifluoromethyl)phenyl]ureaYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(imidazo[1,2-b]pyridazin-6-yloxy)aniline (113 mg, 0.50 mmol) and triethylamine (0.040 mL, 0.29 mmol) in tetrahydrofuran (10 mL) was added 4-(trifluoromethyl)phenyl isocyanate (0.100 mL, 0.70 mmol), and the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was precipitated from methanol to give the title compound (103 mg, 50%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was precipitated from methanol

Sources & evidence

ORD record
ord-4c2ee38bd1124244979a155858815920
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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