Sodium Cyanide → Ethyl 2-(3-(2-(4-fluorobenzylamino)-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

HRID 1882364

Reaktionsgleichung

Reaktionsgleichung von HRID 1882364
C(O[C:4](=[O:23])[CH2:5][N:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:14]([CH3:16])[N:15]=2)[C:7]1=[O:22])C.[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.[C-]#N.[Na+]>ClCCl>[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:4](=[O:23])[CH2:5][N:6]2[CH2:10][CH2:9][N:8]([C:11]3[S:12][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:14]([CH3:16])[N:15]=3)[C:7]2=[O:22])=[CH:27][CH:26]=1

Komponenten

5

Edukt 3

HCID 8929Sodium CyanideHCID 673264-FluorobenzylamineHCID 57919757Ethyl 2-(3-(2-ethoxy-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

Produkt 1

HCID 57919793Ethyl 2-(3-(2-(4-fluorobenzylamino)-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of ethyl 2-(3-(2-ethoxy-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate (0.43 g, 1.25 mmol), 4-fluorobenzylamine (3 mL) and catalytic amount of sodium cyanide was stirred at 80° C. for 16 h. The reaction mixture was allowed to cool to ambient temperature, diluted with dichloromethane (25 mL) and filtered. The solid was washed with dichloromethane and hexanes on the filter. The filtrate was filtered again, and the solid was washed with hexanes. The combined material was dried to afford the title compound as a colorless solid (0.45 g, 86%): 1H NMR (300 MHz, CDCl3) δ 7.28-7.20 (m, 2H), 7.05-6.97 (m, 2H), 6.42 (br s, 1H), 4.42 (d, J=5.7 Hz, 2H), 4.29 (q, J=7.1 Hz, 2H), 4.19-4.10 (m, 2H), 3.99 (s, 2H), 3.77-3.70 (m, 2H), 2.62 (s, 3H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 421.2 (M+1).

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered
  3. washThe solid was washed with dichloromethane and hexanes on the filter
  4. filtrationThe filtrate was filtered again
  5. washthe solid was washed with hexanes
  6. customThe combined material was dried

Quellen und Nachweise

ORD-Eintrag
ord-a691abfff44b454cb867c03d16e2bdb2
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318949B2

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