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

HRID 2095839
Notes
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Reaction equation

HRID 2095839 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 581585166-[(4-Methoxybenzyl)oxy]-3-methylimidazo[1,2-a]pyridin-2-amine

Product 1

HCID 58158603N-{6-[(4-methoxybenzyl)oxy]-3-methylimidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamideYield 60.5%

Reagents, catalysts & solvents

1
HCID 31374DimethylacetamideSolvent

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

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. washThe obtained residue was washed with ethyl acetate
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes