Methyl iodide → 4-{5-[(3-difluoromethoxy-benzenesulfonyl)-methyl-amino]-2-methoxy-phenyl}-piperazine-1-carboxylic Acid tert-butyl Ester

HRID 1710599노트

반응식

HRID 1710599 반응식
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[C:20]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH:33]([F:35])[F:34])[CH:27]=3)(=[O:25])=[O:24])[CH:19]=[CH:18][C:17]=2[O:36][CH3:37])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:38]I>CN(C)C=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[C:20]([N:22]([S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH:33]([F:34])[F:35])[CH:27]=3)(=[O:25])=[O:24])[CH3:38])[CH:19]=[CH:18][C:17]=2[O:36][CH3:37])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 576995064-[5-(3-Difluoromethoxy-benzenesulfonylamino)-2-methoxy-phenyl]-piperazine-1-carboxylic Acid tert-butyl Ester

생성물 1

HCID 576995094-{5-[(3-difluoromethoxy-benzenesulfonyl)-methyl-amino]-2-methoxy-phenyl}-piperazine-1-carboxylic Acid tert-butyl Ester수율 95.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
60 °C

실험 절차

To a suspension of 0.015 g (0.374 mmol) of sodium hydride (60% in paraffin oil) in 2 mL of dimethylformamide 0.16 g of 4-[5-(3-Difluoromethoxy-benzenesulfonylamino)-2-methoxy-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (0.311 mmol) from preparation example 1 were added at room temperature. After stirring for 30 minutes at 60° C., a solution of 0.053 g methyliodide (0.374 mmol) in 1 mL dimethylformamide were added dropwise. Stirring was continued for 16 h at room temperature before the solvent was evaporated. Then, 15 mL of water were added, and the aqueous phase was extracted twice with 10 mL of ethyl acetate each. The organic phases were combined, dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to yield 0.156 g of crude title product which was further purified via silica gel chromatography.

후처리

  1. customfrom preparation example 1
  2. additionwere added at room temperature
  3. stirringStirring
  4. waitwas continued for 16 h at room temperature before the solvent
  5. customwas evaporated
  6. additionThen, 15 mL of water were added
  7. extractionthe aqueous phase was extracted twice with 10 mL of ethyl acetate each
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-f03d216e4c414b22ad638389083321a6
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790727B2

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