m-Tolyl isocyanate → 1-[4-(Imidazo[1,2-b]pyridazin-6-ylethynyl)phenyl]-3-(3-methylphenyl)urea

HRID 589898Notes

Reaction equation

HRID 589898 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([C:10]#[C:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1)=[N:5]2.[C:19]1([CH3:28])[CH:24]=[CH:23][CH:22]=[C:21]([N:25]=[C:26]=[O:27])[CH:20]=1>C1COCC1.O>[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([C:10]#[C:11][C:12]1[CH:13]=[CH:14][C:15]([NH:16][C:26]([NH:25][C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([CH3:28])[CH:20]=3)=[O:27])=[CH:17][CH:18]=1)=[N:5]2

Participants

5

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 1186384084-(Imidazo[1,2-b]pyridazin-6-ylethynyl)aniline

Product 1

HCID 1186384491-[4-(Imidazo[1,2-b]pyridazin-6-ylethynyl)phenyl]-3-(3-methylphenyl)urea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A reaction mixture of 4-(imidazo[1,2-b]pyridazin-6-ylethynyl)aniline (93.6 mg, 0.4 mmol, 1 eq) and m-tolyl isocyanate (0.051 mL, 1 eq) in anhydrous THF (4 mL) was stirred at room temperature for four hours. It was then diluted with water and a solid which precipitated was filtered. The solid was further triturated with ethyl acetate and 1-[4-(imidazo[1,2-b]pyridazin-6-ylethynyl)phenyl]-3-(3-methylphenyl)urea was obtained as a yellow solid upon filtration in amount of 125 mg.

Workup

  1. customa solid which precipitated
  2. filtrationwas filtered
  3. customThe solid was further triturated with ethyl acetate

Sources & evidence

ORD record
ord-1ebd06c3abaa4304a9af8f9a4f87e5b8
Source dataset
uspto-grants-2016_01
Patent number
US09233968B1

Reaction notes

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