Potassium Iodide → 2-(6-{[({[3-(dimethylamino)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione

HRID 1258600노트

반응식

HRID 1258600 반응식
[OH:1][N:2]=[C:3]([C:13]1[N:17]([CH3:18])[N:16]=[N:15][N:14]=1)[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[N:7]([CH3:9])[CH3:8].Br[CH2:20][C:21]1[N:26]=[C:25]([N:27]2[C:35](=[O:36])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]2=[O:37])[CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[CH3:8][N:7]([CH3:9])[C:6]1[CH:5]=[C:4]([C:3](=[N:2][O:1][CH2:20][C:21]2[N:26]=[C:25]([N:27]3[C:28](=[O:37])[C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:35]3=[O:36])[CH:24]=[CH:23][CH:22]=2)[C:13]2[N:17]([CH3:18])[N:16]=[N:15][N:14]=2)[CH:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 112323512-(6-Bromomethyl-pyridin-2-YL)-isoindole-1,3-dioneHCID 1363527053-[(hydroxyimino)(1-methyl-1H-tetrazol-5-yl)methyl]-N,N-dimethylaniline

생성물 1

HCID 866531502-(6-{[({[3-(dimethylamino)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione수율 97%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of 3-[(hydroxyimino)(1-methyl-1H-tetrazol-5-yl)methyl]-N,N-dimethylaniline (2.90 g, 11 mmol) in dry acetonitrile (100 mL) were added 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (3.74 g, 11.8 mmol), cesium carbonate (7.33 g, 22.5 mmol) and potassium iodide (0.89 g, 5.36 mmol). The reaction mixture was stirred at room temperature for 24 h, then insolubles were removed by filtration and washed with dichloromethane. The filtrates were combined and concentrated in vacuo. The residue was dissolved in dichloromethane (500 mL), washed with water (2×200 mL), and the organic layer was dried over MgSO4 and concentrated in vacuo to afford 2-(6-{[({[3-(dimethylamino)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione as an orange solid [5.28 g, yield 97%; HPLC/MS: m/z=483 (M+H); logP(HCOOH)=3.17].

후처리

  1. custominsolubles were removed by filtration
  2. washwashed with dichloromethane
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane (500 mL)
  5. washwashed with water (2×200 mL)
  6. dry with materialthe organic layer was dried over MgSO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f800c35a594d4b6f840de8131e2b1025
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466176B2

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