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

HRID 1711793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711793
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([C:16]=1[C:17]1[CH:18]=[N:19][C:20]([NH:23][NH2:24])=[CH:21][CH:22]=1)[CH:14]=[CH:13][O:12]2.FC1C=CC(C2N=C3N(C=2)C=CO3)=CC=1.[CH2:40]1C(=O)N(I)[C:42](=[O:43])[CH2:41]1.FC1C=CC(B(O)O)=CN=1.NN.[Si](OCCC=O)(C(C)(C)C)(C)C.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CO>[F:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]2[N:10]=[C:11]3[N:15]([C:16]=2[C:17]2[CH:22]=[CH:21][C:20]4[N:19]([C:40]([CH2:41][CH2:42][OH:43])=[N:24][N:23]=4)[CH:18]=2)[CH:14]=[CH:13][O:12]3)=[CH:2][CH:7]=1

Komponenten

9

Edukt 7

HCID 9321HydrazineHCID 120273N-IodosuccinimideHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 36623923-((Tert-butyldimethylsilyl)oxy)propanalHCID 12217721Iodo benzene diacetateHCID 574336106-(4-Fluorophenyl)-imidazo[2,1-b]oxazoleHCID 594578146-(2,4-Difluorophenyl)-5-(6-hydrazinylpyridin-3-yl)imidazo[2,1-b]oxazole

Produkt 1

HCID 594578032-(6-(6-(4-Fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethanolAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

The 6-(2,4-difluorophenyl)-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 with 2-fluoropyridine-5-boronic acid [Asymchem], D with hydrazine) and 3-(tert-butyldimethylsilyloxy)propanal (0.12 g, 0.65 mmol; Toronto) were dissolved in MeOH (5.0 mL) and heated to about 65° C. for about 1 h. The MeOH was evaporated then DCM (5 mL) was added followed by iodobenzene diacetate (0.21 g, 0.65 mmol). The reaction was stirred for about 16 h and then evaporated. The resulting solid was dissolved in 1M TBAF in THF (5 mL). The reaction was allowed to stir for about 30 min. The THF was evaporated and the crude material was purified by reverse phase HPLC (Table 1, Method f). The fractions containing product were concentrated under reduced pressure and the resulting precipitate was filtered and dried under vacuum for about 16 h at about 60° C. to provide the title compound (0.033 g, 14%) as a white solid: LC/MS (Table 1, Method a) Rt=1.76 min; MS m/z: 364.1 (M+H)+.

Aufarbeitung

  1. customprepared
  2. customThe MeOH was evaporated
  3. additionDCM (5 mL) was added
  4. customevaporated
  5. dissolutionThe resulting solid was dissolved in 1M TBAF in THF (5 mL)
  6. stirringto stir for about 30 min
  7. customThe THF was evaporated
  8. customthe crude material was purified by reverse phase HPLC (Table 1, Method f)
  9. additionThe fractions containing product
  10. concentrationwere concentrated under reduced pressure
  11. filtrationthe resulting precipitate was filtered
  12. customdried under vacuum for about 16 h at about 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-6e0462027c774273961b3dfd0c73820d
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790741B2

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