Potassium Carbonate → N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]-2-methylcyclopropanecarboxamide

HRID 1663710Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].I[C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:17]=[C:18]([NH:20][C:21]([CH:23]3[CH2:25][CH:24]3[CH3:26])=[O:22])[N:19]=2)[N:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cl-].[Na+].O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[O:9][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:17]=[C:18]([NH:20][C:21]([CH:23]3[CH2:25][CH:24]3[CH3:26])=[O:22])[N:19]=2)[N:16]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 3-amino-4-fluorophenol (0.42 g, 3.29 mmol) in N,N-dimethylformamide (9.0 mL) were added N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)-2-methylcyclopropanecarboxamide (0.75 g, 2.19 mmol) and potassium carbonate (0.61 g, 4.38 mmol), and the mixture was stirred at 140° C. for 16 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran, washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate alone), and the obtained residue was washed with hexane/ethyl acetate and filtrated to give the title compound (0.63 g, 88%) as a brown powder.

Workup

extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
washwashed with saturated brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltrated
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate alone), and the obtained residue
washwas washed with hexane/ethyl acetate
filtrationfiltrated

Sources & evidence

ORD record: ord-8a0bcf956d5345b69013606bc38fe822
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034812B2

Reaction notes

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