Ethyl Acetate → N-{6-[(4-methoxybenzyl)oxy]-3-methylimidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide

HRID 2095839Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH3:19])=[C:16]([NH2:18])[N:17]=3)[CH:14]=2)=[CH:5][CH:4]=1.[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH3:19])=[C:16]([NH:18][C:25]([CH:22]4[CH2:24][CH2:23]4)=[O:26])[N:17]=3)[CH:14]=2)=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-[(4-methoxybenzyl)oxy]-3-methylimidazo[1,2-a]pyridin-2-amine (1.0 g, 3.53 mmol) in N,N-dimethylacetamide (10 mL) was added cyclopropanecarbonyl chloride (352 μL, 3.88 mmol), and the mixture was stirred at 0° C. for 2 hr. Ethyl acetate and saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was washed with ethyl acetate and collected by filtration to give the title compound (750 mg, 60%) as a slightly-yellow solid.

Workup

extractionthe mixture was extracted 3 times with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was evaporated under reduced pressure
washThe obtained residue was washed with ethyl acetate
filtrationcollected by filtration

Sources & evidence

ORD record: ord-91bcfeb3215a471db5b74e9a7044f094
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445509B2

Reaction notes

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