Sodium Iodide → 2-azido-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindol-4-yl)acetamide

HRID 9989

反応式

HRID 9989 の反応式
[O:1]=[C:2]1[CH:7]([N:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[NH:17][C:18](=[O:21])[CH2:19]Cl)[C:9]2=[O:22])[CH2:6][CH2:5][C:4](=[O:23])[NH:3]1.[N-:24]=[N+:25]=[N-:26].[Na+].[Na+].[I-]>CC(C)=O.ClCCl.O>[N:24]([CH2:19][C:18]([NH:17][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH2:16][N:8]([CH:7]1[CH2:6][CH2:5][C:4](=[O:23])[NH:3][C:2]1=[O:1])[C:9]2=[O:22])=[O:21])=[N+:25]=[N-:26]

参加物

7

反応物 3

HCID 5238Sodium IodideHCID 33557Sodium Azide2 回HCID 98808592-chloro-N-[2-(2,6-dioxo-3-piperidyl)-1-oxo-isoindolin-4-yl]acetamide

生成物 1

HCID 102689262-azido-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindol-4-yl)acetamide収率 93%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred suspension of N-[2-(2,6-dioxo(3-piperidyl))-1-oxoisoindolin-4-yl]-2-chloroacetamide (4.64 g, 13.8 mmol) in acetone (60 ml) was added sodium azide (1.35 g, 20.7 mmol). The mixture was heated to reflux for 18 hours. After 18 hours, to the reaction mixture was added NaI (2.05 g, 13.8 mmol) and additional sodium azide (0.90 g, 13.8 mmol). The mixture was heated at reflux for an additional 18 hours. The solvent was evaporated in vacuo to give an off-white solid which was slurried in a mixture of dichloromethane (50 ml) and H2O (50 ml). This slurry was filtered to give 4.39 g (93%) of product: 1H NMR (DMSO-d6) δ 11.50–9.52 (bs, 2H), 7.87–7.84 (m, 1H), 7.59–7.50 (m, 2H), 5.17 (dd, J=5.0 and 13.1 Hz, 1H), 4.44 (d, J=17.6 Hz, 1H), 4.34 (d, J=17.6 Hz, 1H), 4.13 (s, 2H), 3.00–2.86 (m, 1H), 2.65–2.59 (m, 1H), 2.44–2.29 (m, 1H), 2.07–2.02 (m, 1H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 hours
  3. temperatureThe mixture was heated
  4. temperatureat reflux for an additional 18 hours
  5. customThe solvent was evaporated in vacuo
  6. customto give an off-white solid which
  7. filtrationThis slurry was filtered

出典と根拠

ORDレコード
ord-432839de2b464e6a9c0b3a86be259370
出典データセット
uspto-grants-2006_08
特許番号
US07091353B2

関連ノート

読み込み中…