Sodium hydride → N-(2-(3-methyl-1,2,4-oxadiazol-5-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide

HRID 1519951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519951
[H-].[Na+].[C:3](=[N:6][OH:7])([NH2:5])[CH3:4].[C:8]1([CH2:18][C:19]([NH:21][C:22]2[CH:26]=[CH:25][S:24][C:23]=2[C:27](OC)=O)=[O:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1>C1COCC1.C(OCC)(=O)C>[CH3:4][C:3]1[N:5]=[C:27]([C:23]2[S:24][CH:25]=[CH:26][C:22]=2[NH:21][C:19](=[O:20])[CH2:18][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[O:7][N:6]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 30926N-HydroxyacetamidineHCID 25660569Methyl 3-(2-(naphthalen-1-yl)acetamido)thiophene-2-carboxylate

Produkt 1

HCID 46869074N-(2-(3-methyl-1,2,4-oxadiazol-5-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydride (60% dispersion, 15 mg, 0.39 mmol) was added to a solution of acetamide oxime (29 mg, 0.39 mmol) in THF (1 mL). The resulting mixture was stirred at room temperature for 10 minutes after which a solution of methyl 3-(2-(naphthalen-1-yl)acetamido)thiophene-2-carboxylate (107 mg, 0.33 mmol) in THF (1 mL) was added. The reaction mixture was stirred for 1 h and was subsequently diluted with ethyl acetate (10 mL). The resulting solution was washed with brine (5 mL) and the organic phase was then dried (Na2SO4), filtered and concentrated under vacuum. The residue was dissolved in THF (1 mL) and HCl (1 mL of a 10% aqueous solution) was added. The mixture was stirred for 20 minutes after which ethyl acetate (10 mL) was added. The resulting solution was washed with brine (5 mL) and the organic phase was then dried (Na2SO4), filtered, concentrated under vacuum and the residue was purified by preparative HPLC to give N-(2-(3-methyl-1,2,4-oxadiazol-5-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide. Retention time (min)=9.533, method [7], MS(ESI) 350.1 (M+H). 1H NMR (300 MHz, CDCl3) δ 10.10 (s, 1H), 8.26 (d, J=5.4 Hz, 1H), 8.03 (d, J=9.3 Hz, 2H), 7.59-7.49 (m, 5H), 4.27 (s, 2H), 2.14 (s, 3H).

Aufarbeitung

  1. additionwas added
  2. washThe resulting solution was washed with brine (5 mL)
  3. dry with materialthe organic phase was then dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. dissolutionThe residue was dissolved in THF (1 mL)
  7. additionHCl (1 mL of a 10% aqueous solution) was added
  8. stirringThe mixture was stirred for 20 minutes after which ethyl acetate (10 mL)
  9. additionwas added
  10. washThe resulting solution was washed with brine (5 mL)
  11. dry with materialthe organic phase was then dried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated under vacuum
  14. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0b8a5cd3ed25429fa75f0b460ff3b146
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073891B2

Notizen zur Reaktion

Wird geladen…