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

HRID 1711787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711787
[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]=[CH:18][C:19]4[N:20]([C:22](C(OCC)=O)=[N:23][N:24]=4)[CH:21]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1.FC1C=CC(C2N=C3N(C=2)[CH:42]=[CH:41][O:40]3)=CC=1.[CH2:45]1C(=O)N(I)C(=O)C1.FC1C=CC(B(O)O)=CN=1.NN.O=CC(OCC)=O.C[Mg]Br.[Cl-].[NH4+]>C1COCC1.C(Cl)Cl>[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]=[CH:18][C:19]4[N:20]([C:22]([C:41]([OH:40])([CH3:42])[CH3:45])=[N:23][N:24]=4)[CH:21]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1

Komponenten

11

Edukt 8

HCID 9321HydrazineHCID 25517Ammonium ChlorideHCID 70211Ethyl oxoacetateHCID 120273N-IodosuccinimideHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 574336106-(4-Fluorophenyl)-imidazo[2,1-b]oxazoleHCID 59457829Ethyl 6-(6-(4-fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridine-3-carboxylateHCID 178418573HCID 178418573, Verbindung2×

Produkt 1

HCID 594578242-(6-(6-(4-Fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)propan-2-olAusbeute 4,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

The ethyl 6-(6-(4-fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridine-3-carboxylate (0.250 g, 0.639 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, K.1 with ethyl 2-oxoacetate) was suspended in THF (2.5 mL) then cooled to about −78° C. Methylmagnesium bromide (1.4 M in THF, 1.0 mL, 1.40 mmol) was added and then the mixture was warmed to ambient temperature. Additional methylmagnesium bromide (0.20 mL; 0.28 mmol) was added and then the mixture was stirred for about 15 min. Saturated aqueous ammonium chloride solution (1-2 mL) was added and then the mixture was stirred overnight. The reaction was diluted with DCM and then the layers were separated. The organic solution was dried over MgSO4 and then filtered. The filtrate was evaporated then purified by flash chromatography on 10 g silica gel with 95:5 DCM/MeOH as an eluent to give a residue that was triturated with Et2O/heptane to give the title compound (0.010 g, 4.1% yield): LC/MS (Table 1, Method a) Rt=1.89 min; MS m/z: 378.1 (M+H)+.

Aufarbeitung

  1. customprepared
  2. temperaturethe mixture was warmed to ambient temperature
  3. stirringthe mixture was stirred overnight
  4. customthe layers were separated
  5. dry with materialThe organic solution was dried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customthen purified by flash chromatography on 10 g silica gel with 95:5 DCM/MeOH as an eluent
  9. customto give a residue that
  10. customwas triturated with Et2O/heptane

Quellen und Nachweise

ORD-Eintrag
ord-3a5fe81c8d12404ca796bc8ef8502798
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790741B2

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