Sodium hydride → 4-(tert-butyl)-N-(1-methyl-4-(4-methylphenyl)-3-{2-[(5-nitro-2-pyrimidinyl)oxy]ethoxy}-1H-pyrazol-5-yl)benzenesulphonamide

HRID 1368590ノート

反応式

HRID 1368590 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[N:19]([CH3:20])[N:18]=[C:17]([O:21][CH2:22][CH2:23][OH:24])[C:16]=2[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:35]1[N:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][N:36]=1>C1COCC1.CC(N(C)C)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[N:19]([CH3:20])[N:18]=[C:17]([O:21][CH2:22][CH2:23][O:24][C:35]3[N:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][N:36]=3)[C:16]=2[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 825442-Chloro-5-nitropyrimidineHCID 222820434-(tert-butyl)-N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

生成物 1

HCID 222819704-(tert-butyl)-N-(1-methyl-4-(4-methylphenyl)-3-{2-[(5-nitro-2-pyrimidinyl)oxy]ethoxy}-1H-pyrazol-5-yl)benzenesulphonamide収率 146.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4-(tert-butyl)-N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-benzenesulphonamide (Example 2) (1838 mg) in anhydrous THF (18 ml) at 0° C. stirred under an atmosphere of nitrogen was added sodium hydride (60% dispersion in oil, 348 mg) A precipitate began to form which was stirred at 0° C. for 15 min. 2-Chloro-5-nitropyrimidine (Wempen, I.; Blank, H. U.; Fox, J. J. J. Heterocyclic Chem. 1969, 6, 593. Hurst, D. T.; Heterocycles 1984, 22, 79; Heterocycles, 1977, 6, 1999-2004.) (661 mg) in anhydrous DMA (3 ml) was added dropwise and the solution was allowed to warm to room temperature. The reaction was quenched after 130 min by cautiously pouring the mixture onto a vigorously stirred mixture of ethyl acetate (300 ml) and saturated ammonium chloride solution (300 ml). The ethyl acetate layer was separated off, dried (MgSO4) and evaporated to dryness. This afforded a yellow residue (3.44 g) which was purified by column chromatography on silica gel (256 g), eluting with a gradient of ethyl acetate:hexane (4:5 to 5:4).

後処理

  1. customto form which
  2. temperatureto warm to room temperature
  3. customThe reaction was quenched after 130 min
  4. additionby cautiously pouring the mixture
  5. additiononto a vigorously stirred mixture of ethyl acetate (300 ml) and saturated ammonium chloride solution (300 ml)
  6. customThe ethyl acetate layer was separated off
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness

出典と根拠

ORDレコード
ord-0b4b3c5346d147e1977e6f2c1aba5dae
出典データセット
uspto-grants-2003_06
特許番号
US06573270B1

反応ノート

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