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

HRID 1667966

Reaction equation

HRID 1667966 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-fc8307c13a8b4d439acd0e195499c420
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Linked notes

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