Hydrazine → 3-(6-(6-(4-Fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-2,2-dimethylpropanoic acid

HRID 1711796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711796
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:17]=[N:18][C:19]([NH:22][NH2:23])=[CH:20][CH:21]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1.FC1C=CC(C2N=C3N(C=2)C=CO3)=CC=1.C1C(=O)N(I)C(=O)C1.FC1C=CC(B(O)O)=CN=1.NN.[CH3:59][C:60]1([CH3:67])[CH2:64][C:63](=O)[O:62][C:61]1=[O:66]>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][C:19]4[N:18]([C:63]([CH2:64][C:60]([CH3:67])([CH3:59])[C:61]([OH:66])=[O:62])=[N:23][N:22]=4)[CH:17]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1

Komponenten

8

Edukt 6

HCID 9321HydrazineHCID 870672,2-Dimethylsuccinic anhydrideHCID 120273N-IodosuccinimideHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 574336106-(4-Fluorophenyl)-imidazo[2,1-b]oxazoleHCID 594577926-(4-Fluorophenyl)-5-(6-hydrazinylpyridin-3-yl)imidazo[2,1-b]oxazole

Produkt 1

HCID 594578573-(6-(6-(4-Fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-2,2-dimethylpropanoic acidAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a 100 mL round-bottom flask 6-(4-fluorophenyl)-5-(6-hydrazinylpyridin-3-yl)imidazo[2,1-b]oxazole (0.20 g, 0.65 mmol; prepared using A from 6-(4-fluorophenyl)-imidazo[2,1-b]oxazole [prepared according to WO2004110990A2, Example 1, Steps 1-3] with NIS, C using 2-fluoropyridine-5-boronic acid [Asymchem], D using hydrazine) and 3,3-dimethyldihydrofuran-2,5-dione (0.091 g, 0.71 mmol) were dissolved in 1,4-dioxane (5 mL) and the mixture was heated to about 100° C. After about 2 h the reaction was cooled to ambient temperature and concentrated in vacuo. The crude material was dissolved in DCM and crystallized upon the addition of Et2O. The resulting solid was filtered and dried under vacuum to provide the title compound as a white solid (0.22 g, 81%): LC/MS (Table 1, Method a) Rt, =1.86 min; MS m/z: 420.2 (M+H)+.

Aufarbeitung

  1. customprepared
  2. temperatureAfter about 2 h the reaction was cooled to ambient temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude material was dissolved in DCM
  5. customcrystallized upon the addition of Et2O
  6. filtrationThe resulting solid was filtered
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2b1e1133338449c0904775669f4dbcda
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790741B2

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