Dimethylformamide → N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]-N2,N2-dimethylglycinamide

HRID 2391277

Reaction equation

HRID 2391277 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12](=[O:17])[CH2:13][N:14]([CH3:16])[CH3:15])[N:10]=2)[N:7]=1.[NH2:18][C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[NH2:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=1)[O:25][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12](=[O:17])[CH2:13][N:14]([CH3:16])[CH3:15])[N:10]=2)[N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 115683-AminophenolHCID 57708588N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)-N2,N2-dimethylglycinamide

Product 1

HCID 57708553N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]-N2,N2-dimethylglycinamideYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)-N2,N2-dimethylglycinamide (517 mg, 1.5 mmol), 3-aminophenol (491 mg, 4.5 mmol), potassium carbonate (415 mg, 3.0 mmol) and N,N-dimethylformamide (3.0 mL) was stirred using a microwave synthesizer at 180° C. for 40 min. The reaction mixture was diluted with water, and the precipitate was collected by filtration, washed with water, and dried under reduced pressure. The obtained solid was washed with ethyl acetate to give the title compound (410 mg, 84%) as a brown powder.

Workup

  1. customat 180° C.
  2. customfor 40 min
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure
  6. washThe obtained solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-eda05bd8861848bc874f746cb56d6f38
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Linked notes

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