Pyridine → N-[4-(3-benzyl-[1,2,4]oxadiazol-5-yl)-pyridin-2-yl]-benzamide

HRID 714350

Reaktionsgleichung

Reaktionsgleichung von HRID 714350
[C:1]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][N:18]=1)[C:13]([OH:15])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.O[N:26]=[C:27]([NH2:35])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.N1C=CC=CC=1.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>ClCCl.CN(C)C=O.C(OCC)(=O)C>[CH2:28]([C:27]1[N:35]=[C:13]([C:12]2[CH:16]=[CH:17][N:18]=[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:11]=2)[O:15][N:26]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Komponenten

9

Edukt 5

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 2731007N'-hydroxy-2-phenylethanimidamideHCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 64393851HCID 64393851, Verbindung

Produkt 1

HCID 67153834N-[4-(3-benzyl-[1,2,4]oxadiazol-5-yl)-pyridin-2-yl]-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-benzamidoisonicotinic acid (0.35 g, 1.44 mmol) and N,N-dimethylformamide (0.1 mL) in dichloromethane (5 mL) was added oxalyl chloride (0.15 mL, 1.73 mmol) at ambient temperature. The resulting mixture was stirred at ambient temperature for 1 hour and concentrated in vacuo to dryness. The residue was dissolved in N,N-dimethylformamide (2 mL) and added to a solution of N′-hydroxy-2-phenylacetimidamide (0.24 g, 1.59 mmol) and pyridine (0.3 mL, 3.70 mmol) in N,N-dimethylformamide (1 mL) at 0° C. The reaction mixture was stirred at ambient temperature for 3 hours, diluted with ethyl acetate (40 mL), washed with water (20 mL) and brine (20 mL). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was dissolved in toluene (10 mL), followed by the addition of (methoxycarbonylsulfamoyl)triethylammonium hydroxide (0.53 g, 2.16 mmol). The mixture was refluxed for 1 hour and concentrated in vacuo. The residue was purified by column chromatography to give N-[4-(3-benzyl-[1,2,4]oxadiazol-5-yl)-pyridin-2-yl]-benzamide as a colorless solid (0.06 g 12%): mp 150-151° C.; 1H NMR (300 MHz, CDCl3) δ 9.06 (s, 1H), 8.69 (s, 1H), 8.46 (d, J=4.9 Hz, 1H), 7.94-7.91 (m, 2H), 7.72-7.69 (m, 1H), 7.62-7.48 (m, 3H), 7.39-7.24 (m, 5H), 4.16 (s, 2H); MS (ES+) m/z 357.5 (M+1).

Aufarbeitung

  1. concentrationconcentrated in vacuo to dryness
  2. dissolutionThe residue was dissolved in N,N-dimethylformamide (2 mL)
  3. stirringThe reaction mixture was stirred at ambient temperature for 3 hours
  4. washwashed with water (20 mL) and brine (20 mL)
  5. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in toluene (10 mL)
  9. temperatureThe mixture was refluxed for 1 hour
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a056803727484e82aaaf77c0a5bf2208
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187426B2

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