Toluene → HCID 24768004, compound

HRID 1664052Notes

Reaction equation

HRID 1664052 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[N:11]=1.[F:24][C:25]([F:36])([F:35])[C:26]1[CH:27]=[C:28]([N:32]=[C:33]=[O:34])[CH:29]=[CH:30][CH:31]=1.C1(C)C=CC=CC=1>O1CCCC1>[F:24][C:25]([F:35])([F:36])[C:26]1[CH:27]=[C:28]([NH:32][C:33]([NH:1][C:2]2[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=2)[O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]4[CH2:20][CH2:19]4)=[O:17])[N:14]=3)[N:11]=2)=[O:34])[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 57386059N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 24768004HCID 24768004, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (300 mg, 0.969 mmol), 3-(trifluoromethyl)phenyl isocyanate (667 μL, 4.84 mmol), toluene (4 mL) and tetrahydrofuran (1 mL) was stirred with heating under reflux for 3 hr. After the reaction mixture was allowed to cool to room temperature, the precipitate was collected by filtration and washed with ethyl acetate/diisopropyl ether to give the title compound (268 mg, 56%) as a white powder.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hr
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-28e098a4ab62413cb71546f4567539d7
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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