Acrylamide → 1-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indole

HRID 2073545

Reaktionsgleichung

Reaktionsgleichung von HRID 2073545
[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[CH:13]3)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[C:21]([NH2:25])(=[O:24])[CH:22]=[CH2:23].[Cl-].[NH4+]>CN(C)C=O>[C:21]([CH2:22][CH2:23][N:15]1[C:16]2[C:12](=[CH:11][C:10]([C:8](=[O:9])[NH:7][CH2:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:18][CH:17]=2)[CH:13]=[CH:14]1)(=[O:24])[NH2:25]

Komponenten

6

Edukt 4

HCID 6579AcrylamideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 100373961h-Indole-5-carboxamide,n-(cyclopentylmethyl)-

Produkt 1

HCID 198224771-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indoleAusbeute 36,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 5-(N-cyclopentylmethylcarbamoyl)indole (A) (1.50 g) in N,N-dimethylformamide (DMF) (5 ml) was added to a stirred slurry of sodium hydride (0.16 g) in DMF (15 ml) maintained at 0° C. under an atmosphere of nitrogen. The mixture was warmed to room temperature for 15 minutes, treated with a solution of acrylamide (0.66 g) in DMF (5 ml), and allowed to stir for 12 hours. The mixture was poured into a cold, saturated aqueous solution of ammonium chloride to give a milky suspension which was extracted with ethyl acetate. The organic phase was washed successively with water and brine, dried (MgSO4), and evaporated. The resulting clear oil was purified by flash chromatography on silica gel (700 ml), eluting with 7:93 v/v methanol:ethyl acetate, to give 1-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indole (0.70 g, 36%) as a gummy white foam; NMR (80 MHz, CDCl3): 1.2-2.2(broad m, 9H, cyclopentyl), 2.7(t, 2H, CH2CO), 3.4(dd, 2H, CH2NH), 4.5(t, 2H, CH2CH2CO), 5.4(broad, 2H, CONH2), 6.5(dd, 1H, H3 -indole), 7.2(d, 1H, H2 -indole), 7.3(d, 1H, H7 -indole), 7.6(dd, 1H, H6 -indole), 8.0(m, 1H, H4 -indole).

Aufarbeitung

  1. temperatureThe mixture was warmed to room temperature for 15 minutes
  2. customto give a milky suspension which
  3. extractionwas extracted with ethyl acetate
  4. washThe organic phase was washed successively with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe resulting clear oil was purified by flash chromatography on silica gel (700 ml)
  8. washeluting with 7:93 v/v methanol

Quellen und Nachweise

ORD-Eintrag
ord-ab9345e05c5441c6b5bd0c7509b0dd0c
Quelldatensatz
uspto-grants-1990_04
Patentnummer
US04918094

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