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

HRID 2391314Notes

Reaction equation

[CH:1]1([CH2:4][C:5]([NH:7][C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13](I)=[N:12][N:11]3[CH:17]=2)=[O:6])[CH2:3][CH2:2]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>[Cl-].[Na+].O.O1CCCC1.C(OCC)(=O)C>[NH2:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=1)[O:25][C:13]1[CH:14]=[CH:15][C:10]2[N:11]([CH:17]=[C:8]([NH:7][C:5](=[O:6])[CH2:4][CH:1]3[CH2:3][CH2:2]3)[N:9]=2)[N:12]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-cyclopropyl-N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide (501 mg, 1.46 mmol), 3-aminophenol (479 mg, 4.39 mmol), potassium carbonate (807 mg, 5.84 mmol) and N,N-dimethylformamide (5 mL) was stirred at 120° C. for 12 hr. Tetrahydrofuran/ethyl acetate and saturated brine were added to the reaction mixture, and insoluble material was filtered off. The filtrate was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/80→0/100) to give the title compound (156 mg, 33%) as a pale-yellow powder.

Workup

filtrationwas filtered off
extractionThe filtrate was extracted with ethyl acetate
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltrated
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/80→0/100)

Sources & evidence

ORD record: ord-3f621dd2d2c34f61b7ac6bf0b194ee7b
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273741B2

Reaction notes

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