Sodium Iodide → 2-azido-N-[[2-(2,6-dioxo-3-piperidyl)-1,3-dioxo-isoindolin-4-yl]methyl]acetamide

HRID 9968

반응식

HRID 9968 반응식
Cl[CH2:2][C:3]([NH:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9](=[O:25])[N:10]([CH:17]1[CH2:22][CH2:21][C:20](=[O:23])[NH:19][C:18]1=[O:24])[C:11]2=[O:16])=[O:4].[N-:26]=[N+:27]=[N-:28].[Na+].[I-].[Na+]>CC(C)=O>[N:26]([CH2:2][C:3]([NH:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9](=[O:25])[N:10]([CH:17]1[CH2:22][CH2:21][C:20](=[O:23])[NH:19][C:18]1=[O:24])[C:11]2=[O:16])=[O:4])=[N+:27]=[N-:28]

참가 물질

5

반응물 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 10270102TNF-alpha-IN-1

생성물 1

HCID 101096912-azido-N-[[2-(2,6-dioxo-3-piperidyl)-1,3-dioxo-isoindolin-4-yl]methyl]acetamide수율 90.8%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of 2-chloro-N-{[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]methyl}acetamide (1.3 g, 3.57 mmol), sodium azide (0.3 g, 4.65 mmol) and sodium iodide (0.54 g, 3.57 mmol) in acetone (50 ml) was refluxed for 17 hours. The solvent was removed in vacuo and the residue was dissolved in EtOAc (60 ml). The EtOAc solution was washed with H2O (30 ml), brine (30 ml), and dried (MgSO4). The solvent was removed in vacuo to give 2-azido-N-{[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]methyl}acetamide (1.2 g, 90%) as a white solid: 1H NMR (CDCl3) δ d 8.48 (s, 1H), 7.84–7.68 (m, 3H), 7.51 (t, J=6.3 Hz, 1H), 5.04–4.97 (dd, J=4.7 and 11.8 Hz, 1H), 4.80 (d, J=6.5 Hz, 2H), 3.97 (s, 2H), 2.95–2.74 (m, 3H), 2.20–2.15 (m, 1H).

후처리

  1. temperaturewas refluxed for 17 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in EtOAc (60 ml)
  4. washThe EtOAc solution was washed with H2O (30 ml), brine (30 ml)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-7fef32c3685e4b6683f832c20f4ac0ba
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091353B2

연결된 노트

불러오는 중…