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

HRID 707353노트

반응식

HRID 707353 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1904e432163f4c44a24d225e2a2fd841
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174992B2

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