Ethylene carbonate → 2-[2-(4-Benzyloxy-2-fluoro-phenyl)-4-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-imidazol-1-yl]-ethanol

HRID 1800320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1800320
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][CH:17]=[C:18]([C:20]3[N:24]([CH:25]([CH3:27])[CH3:26])[N:23]=[CH:22][N:21]=3)[N:19]=2)=[C:11]([F:28])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:29]1[CH2:33][CH2:32]OC1=O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH2:32][CH2:33][OH:29])[CH:17]=[C:18]([C:20]3[N:24]([CH:25]([CH3:26])[CH3:27])[N:23]=[CH:22][N:21]=3)[N:19]=2)=[C:11]([F:28])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 7303Ethylene carbonateHCID 178456684HCID 178456684, Verbindung

Produkt 1

HCID 582042922-[2-(4-Benzyloxy-2-fluoro-phenyl)-4-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-imidazol-1-yl]-ethanolAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A suspension of 5-[2-(4-benzyloxy-2-fluoro-phenyl)-1H-imidazol-4-yl]-1-isopropyl-1H-[1,2,4]triazole (84 g, 0.22 mol) and [1,3]dioxolan-2-one (48 g, 0.55 mol) in toluene (100 mL) was heated at 130° C. for 7.5 h allowing some solvent to evaporate until reaction was initiated. The cooled reaction mixture was concentrated in vacuo and the residue treated with acetonitrile (50 mL), stirred, sonicated and cooled in an ice bath. The resultant solid was collected by filtration, washed with cold acetonitrile then diethyl ether and dried in vacuo at 60° C. to give 2-[2-(4-Benzyloxy-2-fluoro-phenyl)-4-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-imidazol-1-yl]-ethanol (65.2 g, 70%). 1H NMR (400 MHz, CDCl3): 8.04 (1H, s), 7.80 (1H, d, J=0.71 Hz), 7.43-7.41 (6H, m), 6.89 (1H, dd, J=8.59, 2.50 Hz), 6.79 (1H, dd, J=11.73, 2.47 Hz), 5.93-5.92 (1H, m), 5.11 (2H, s), 4.02 (2H, t, J=4.93 Hz), 3.89 (2H, t, J=4.96 Hz), 1.49 (6H, d, J=6.61 Hz). LCMS: RT=3.30 min, [M+H]+=422.

Aufarbeitung

  1. customto evaporate until reaction
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo
  4. additionthe residue treated with acetonitrile (50 mL)
  5. customsonicated
  6. temperaturecooled in an ice bath
  7. filtrationThe resultant solid was collected by filtration
  8. washwashed with cold acetonitrile
  9. dry with materialdiethyl ether and dried in vacuo at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-9008be778e1b4b38bd58b8802aa786b1
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343955B2

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