Dimethylformamide → HCID 57441058, compound

HRID 2391306Notes

Reaction equation

HRID 2391306 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH2:11])[N:10]=2)[N:7]=1.[NH2:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[NH2:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[O:19][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH2:11])[N:10]=2)[N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 115683-AminophenolHCID 574410246-Iodoimidazo[1,2-B]pyridazin-2-amine

Product 1

HCID 57441058HCID 57441058, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-iodoimidazo[1,2-b]pyridazin-2-amine (390 mg, 1.5 mmol), 3-aminophenol (491 mg, 4.5 mmol), potassium carbonate (415 mg, 3.0 mmol) and N,N-dimethylformamide (3 mL) was stirred using a microwave synthesizer at 180° C. for 40 min. The reaction mixture was diluted with water and extracted with a mixed solvent of ethyl acetate/tetrahydrofuran (1:1). The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→60/40). The objective fraction was concentrated under reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate/methanol=100/0→80/20) and precipitated from ethyl acetate to give the title compound (133 mg, yield 37%) as a purple solid.

Workup

  1. customat 180° C.
  2. customfor 40 min
  3. extractionextracted with a mixed solvent of ethyl acetate/tetrahydrofuran (1:1)
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→60/40)
  6. concentrationThe objective fraction was concentrated under reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (ethyl acetate/methanol=100/0→80/20)
  8. customprecipitated from ethyl acetate

Sources & evidence

ORD record
ord-01bb963b2c25417fa9607408cb9f52de
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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