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

HRID 1062768

反応式

HRID 1062768 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0dcca56b30dc4d7f9112bb516073bf55
出典データセット
uspto-grants-2005_11
特許番号
US06962923B2

関連ノート

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