Sodium hydride → 2-{[5-{[(4-tert-butylphenyl)sulfonyl]amino}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl Acetate

HRID 1062768

반응식

HRID 1062768 반응식
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[C:11]([NH2:20])[N:10]([CH3:21])[N:9]=1)(=[O:3])[CH3:2].[H-].[Na+].[C:24]([C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25]>CC(N(C)C)=O.O>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)=[C:11]([NH:20][S:34]([C:31]2[CH:32]=[CH:33][C:28]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:29][CH:30]=2)(=[O:36])=[O:35])[N:10]([CH3:21])[N:9]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 222820022-{[5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate

생성물 1

HCID 222819582-{[5-{[(4-tert-butylphenyl)sulfonyl]amino}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl Acetate수율 24.3%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

실험 절차

To 2-{[5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (Preparation 5) (250 mg) in dimethyl acetamide (2 ml) at room temperature was added sodium hydride (41 mg, 60% dispersion in oil), the mixture was stirred for 5 minutes. To the mixture was added 4-tert-butylbenzenesulphonyl chloride (79 mg), the mixture was stirred for a further 1 hour. The reaction was diluted with water (20 ml) and extracted with diethyl ether (20 ml). The organic fraction was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 10 g) eluted with dichloromethane:ether (1:1) to yield the title compound as a pale orange solid (40 mg).

후처리

  1. stirringthe mixture was stirred for a further 1 hour
  2. extractionextracted with diethyl ether (20 ml)
  3. dry with materialThe organic fraction was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica, 10 g)
  7. washeluted with dichloromethane:ether (1:1)

출처 및 근거

ORD 기록
ord-0dcca56b30dc4d7f9112bb516073bf55
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06962923B2

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