Sodium hydride → 2-[1-(2-Butyl4-oxo-1,3-diaza-spiro[4.4]non-1-en-3-yl)-indan-5-yl]-benzonitrile

HRID 1742408

反応式

HRID 1742408 の反応式
[H-].[Na+].[CH2:3]([C:7]1[NH:11][C:10](=[O:12])[C:9]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[N:8]=1)[CH2:4][CH2:5][CH3:6].Cl[CH:18]1[C:26]2[C:21](=[CH:22][C:23]([C:27]3[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=3[C:29]#[N:30])=[CH:24][CH:25]=2)[CH2:20][CH2:19]1>O1CCOCC1>[CH2:3]([C:7]1[N:11]([CH:18]2[C:26]3[C:21](=[CH:22][C:23]([C:27]4[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=4[C:29]#[N:30])=[CH:24][CH:25]=3)[CH2:20][CH2:19]2)[C:10](=[O:12])[C:9]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[N:8]=1)[CH2:4][CH2:5][CH3:6]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 101765112-Butyl-1,3-diazaspiro[4.4]non-1-en-4-oneHCID 152289522-(1-Chloro-indan-5-yl)-benzonitrile

生成物 1

HCID 190089202-[1-(2-Butyl4-oxo-1,3-diaza-spiro[4.4]non-1-en-3-yl)-indan-5-yl]-benzonitrile収率 30.9%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
110 °C

実験手順

Sodium hydride (53 mg, 2.3 mmol) was added to 2-butyl-1,3-diaza-spiro[4.4]non-1-en-4-one (458 mg, 2.36 mmol) in anhydrous 1,4-dioxane (3 mL). After 0.25 hour, a solution of 2-(1-chloro-indan-5-yl)-benzonitrile (300 mg, 1.18 mmol)in dioxane (1.0 mL) was added. The reaction mixture was heated at 110° C. for 20 hours, cooled to room temperature and concentrated in vacuo. The crude residue was chromatographed on SiO2 -gel using 50% ethyl acetate/hexanes to give 150 mg of a colorless oil. 1H NMR (250 MHz, CDCl3): d 7.80 (d, 1 H), 7.65 (q, 1 H), 7.48 (m, 4 H), 7.10 (d, 1 H), 5.75 (m, 1 H), 3.42 (m), 3.15 (m), 2.85 (m), 2.55 (m), 2.40-1.60 (m), 1.40 (m), 0.88 (t, 3 H).

後処理

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was chromatographed on SiO2

出典と根拠

ORDレコード
ord-2e97e82659fa4c8094f17fe795a956ae
出典データセット
uspto-grants-1994_08
特許番号
US05338740

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