Ethylene carbonate → 2-[2-(4-Chloro-6-methoxy-pyridin-3-yl)-4-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-imidazol-1-yl]-ethanol

HRID 1530468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1530468
[Cl:1][C:2]1[C:7]([C:8]2[NH:9][CH:10]=[C:11]([C:13]3[N:14]([CH:19]([CH3:21])[CH3:20])[N:15]=[C:16]([CH3:18])[N:17]=3)[N:12]=2)=[CH:6][N:5]=[C:4]([O:22][CH3:23])[CH:3]=1.C1(=O)O[CH2:27][CH2:26][O:25]1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([O:22][CH3:23])[N:5]=[CH:6][C:7]=1[C:8]1[N:9]([CH2:27][CH2:26][OH:25])[CH:10]=[C:11]([C:13]2[N:14]([CH:19]([CH3:21])[CH3:20])[N:15]=[C:16]([CH3:18])[N:17]=2)[N:12]=1

Komponenten

4

Edukt 2

HCID 7303Ethylene carbonateHCID 178491889HCID 178491889, Verbindung

Produkt 1

HCID 582045242-[2-(4-Chloro-6-methoxy-pyridin-3-yl)-4-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-imidazol-1-yl]-ethanolAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A suspension of 4-chloro-5-[4-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-1H-imidazol-2-yl]-2-methoxy-pyridine (5.9 g, 17.7 mmol) in toluene (20 mL) was treated with ethylene carbonate (50 mL) and heated at 130° C. for 2.5 h. The cooled reaction mixture was concentrated in vacuo then diluted with DCM and passed through a pad of silica eluting with DCM then 20% methanol in DCM. Methanolic fractions were combined and concentrated in vacuo and the resultant residue subjected to recrystallisation from acetonitrile to give the title compound as a pale tan solid (2.27 g, 34%). LCMS: RT=2.53 min [M+H]+ =377/379. 1H NMR 400 MHz (CDCl3) δ: 8.25 (1H, s), 8.05 (1H, s), 6.92 (1H, s), 5.82-5.80 (1H, m), 4.00 (3H, s), 3.97 (2H, t, J=4.92 Hz), 3.88 (2H, t, J=4.92 Hz), 2.38 (3H, s), 1.48 (6H, d, J=6.63 Hz).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated in vacuo
  3. additionthen diluted with DCM
  4. concentrationconcentrated in vacuo
  5. customthe resultant residue subjected to recrystallisation from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-ad947268ccb1478c92ed0453c2e8708c
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090628B2

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