Sodium Carbonate → N-methoxy-N-methyl-3-((3-nitropyridin-2-yl)amino)cyclobutanecarboxamide

HRID 707353Notes

Reaction equation

HRID 707353 reaction equation
[NH2:1][CH:2]1[CH2:5][CH:4]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])[CH2:3]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=1>CN(C)C=O.O>[CH3:11][O:10][N:8]([CH3:9])[C:6]([CH:4]1[CH2:5][CH:2]([NH:1][C:19]2[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:3]1)=[O:7]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 450845023-amino-N-methoxy-N-methylcyclobutanecarboxamide

Product 1

HCID 86694209N-methoxy-N-methyl-3-((3-nitropyridin-2-yl)amino)cyclobutanecarboxamideYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-amino-N-methoxy-N-methylcyclobutanecarboxamide (0.606 g, 3.84 mmol) in dry dimethylformamide (15 mL) was added sodium carbonate (1.22 g, 11.5 mmol) and 2-chloro-3-nitropyridine (608 mg, 3.84 mmol). The reaction mixture was stirred and heated at reflux for 14 hours. The reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate (2×30 mL). The combined organic extracts were washed with water (30 mL), brine (30 mL) and dried over sodium sulfate. The filtrate was evaporated in vacuo and the residue was purified by column chromatography on silica gel (20% to 50% ethyl acetate in petroleum ether) to give N-methoxy-N-methyl-3-((3-nitropyridin-2-yl)amino)cyclobutanecarboxamide (0.86 g, 3.07 mmol, 80% yield) as yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 14 hours
  3. extractionextracted with ethyl acetate (2×30 mL)
  4. washThe combined organic extracts were washed with water (30 mL), brine (30 mL)
  5. dry with materialdried over sodium sulfate
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was purified by column chromatography on silica gel (20% to 50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-1904e432163f4c44a24d225e2a2fd841
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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