Dimethylformamide → HCID 57505458, compound

HRID 2391192Notes

Reaction equation

HRID 2391192 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])[N:10]=2)[N:7]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.O1CCCC1.C(OCC)(=O)C>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:2]2[CH:3]=[CH:4][C:5]3[N:6]([CH:8]=[C:9]([NH:11][C:12]([CH:14]4[CH2:16][CH2:15]4)=[O:13])[N:10]=3)[N:7]=2)=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 37588824-Amino-3-NitrophenolHCID 57386058N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

Product 1

HCID 57505458HCID 57505458, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide (656 mg, 2.00 mmol), 4-amino-3-nitrophenol (616 mg, 4.00 mmol), potassium carbonate (411 mg, 3.00 mmol) and N,N-dimethylformamide (6.0 mL) was stirred at 150° C. for 3 hr. After allowing the reaction mixture to cool to room temperature, ethyl acetate (100 mL), tetrahydrofuran (40 mL) and water (40 mL) were added to the mixture, and the insoluble material was filtered through celite. The organic layer was collected from the filtrate, washed with saturated aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate, and filtrated. Dichloromethane (20 mL) was added to the residue, and the precipitate was collected by filtration to give the title compound (367 mg, 52%). The filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/19→ethyl acetate alone) to give the title compound (125 mg, 18%) as a white solid.

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe insoluble material was filtered through celite
  3. customThe organic layer was collected from the filtrate
  4. washwashed with saturated aqueous sodium hydrogencarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. additionDichloromethane (20 mL) was added to the residue
  8. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-e6001539aa744ba484311e105590dd99
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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