Cesium carbonate → Diethyl 2-(4-tert-butoxycarbonylaminobutyl)-2-[1-(5-cyclopropyl-[1,3,4]thiadiazol-2-ylmethyl)-1H-imidazol-4-yl]malonate

HRID 1666986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666986
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:8][C:9]1[S:10][C:11]([CH:14]2[CH2:16][CH2:15]2)=[N:12][N:13]=1.[C:17]([O:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([C:40]1[N:41]=[CH:42][NH:43][CH:44]=1)([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[C:17]([O:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([C:40]1[N:41]=[CH:42][N:43]([CH2:8][C:9]2[S:10][C:11]([CH:14]3[CH2:16][CH2:15]3)=[N:12][N:13]=2)[CH:44]=1)([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:23])([CH3:19])([CH3:20])[CH3:18]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 27576792-(Chloromethyl)-5-cyclopropyl-1,3,4-thiadiazoleHCID 178471441HCID 178471441, Verbindung

Produkt 1

HCID 67443151Diethyl 2-(4-tert-butoxycarbonylaminobutyl)-2-[1-(5-cyclopropyl-[1,3,4]thiadiazol-2-ylmethyl)-1H-imidazol-4-yl]malonateAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Together with 1.97 g (6.04 mmol) of cesium carbonate and 0.29 g (1.66 mmol) of 2-chloromethyl-5-cyclopropyl-1,3,4-thiadiazole, a solution of 0.60 g (1.51 mmol) of diethyl 2-(4-tert-butoxycarbonylaminobutyl)-2-(1H-imidazol-4-yl)malonate in 12 ml of DMF was heated at 75° C. for 2 h. The reaction mixture was concentrated under reduced pressure, and the residue was taken up in ethyl acetate and washed with water. The organic phase was dried over Na2SO4, filtered and concentrated. Chromatographic purification of the residue on silica gel (CH2Cl2:MeOH:water:acetic acid 95:5:0.5:0.5) gave 0.145 g (18%) of the title compound.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washwashed with water
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customChromatographic purification of the residue on silica gel (CH2Cl2:MeOH:water:acetic acid 95:5:0.5:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-264ef64331ce40d6b8eaf08f6d8f4d28
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044208B2

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