Dimethylformamide → HCID 72188742, Verbindung

HRID 625114

Reaktionsgleichung

Reaktionsgleichung von HRID 625114
[CH3:1][O:2][C:3]1[S:7][C:6]2=[N:8][C:9]([C:11]3[O:12][C:13]4[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH2:23][C:24]#[CH:25])[C:14]=4[CH:15]=3)=[CH:10][N:5]2[N:4]=1.[N:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[N+:27]=[N-:28].CN(C=O)C>>[CH3:1][O:2][C:3]1[S:7][C:6]2=[N:8][C:9]([C:11]3[O:12][C:13]4[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH2:23][C:24]5[N:26]([C:29]6[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=6)[N:27]=[N:28][CH:25]=5)[C:14]=4[CH:15]=3)=[CH:10][N:5]2[N:4]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 69319AzidobenzeneHCID 867008962-Methoxy-6-(6-methoxy-4-(prop-2-yn-1-yloxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazole

Produkt 1

HCID 72188742HCID 72188742, VerbindungAusbeute 14 %

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

In a 5 mL microwave vial, was added 2-methoxy-6-(6-methoxy-4-(prop-2-yn-1-yloxy)benzofuran-2-yl)imidazo[2,1-b][1,3,4]thiadiazole (Example 9A, 27 mgs, 0.076 mmol), azidobenzene (Example 9B, 30 mgs, 0.252 mmol), anhydrous DMF (2.5 mL, 32.3 mmol) and (Cp*RuCl)4 (12 mgs) under a nitrogen atmosphere. The vial was capped and heated at 110° C. for 20 min. in the microwave apparatus. The solvent was evaporated and the residue was purified by silica gel chromatography ISCO, concentrated and twice triturated with methanol (2×1 mL). To the solid was added acetonitrile (2 mL) and water (4 mL) and the mixture was freeze dried over the weekend to give the title material (5 mgs, 10.54 μmol, 14% yield). LC (Method F): 2.480 min. HRMS (ESI) calcd for C23H19N6O4S [M+H]+ m/z 475.1183, found 475.1234. 1H NMR (DMSO-d6, 400 MHz) δ ppm: 8.35 (s, 1H), 8.12 (s, 1H), 7.66-7.73 (m, 2H), 7.53-7.63 (m, 3H), 6.84 (dd, J=2.0, 0.8 Hz, 1H), 6.75 (d, J=0.8 Hz, 1H), 5.40 (s, 2H), 4.20 (s, 3H), 3.79 (s, 3H).

Aufarbeitung

  1. customThe vial was capped
  2. customThe solvent was evaporated
  3. customthe residue was purified by silica gel chromatography ISCO
  4. concentrationconcentrated
  5. customtwice triturated with methanol (2×1 mL)
  6. additionTo the solid was added acetonitrile (2 mL) and water (4 mL)
  7. customdried over the weekend

Quellen und Nachweise

ORD-Eintrag
ord-084261f64a63451c834b706c3bd57de0
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303065B2

Verknüpfte Notizen

Wird geladen…