Aluminium lithium hydride → HCID 178509926, Verbindung

HRID 505555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505555
[Cl:1][C:2]1[C:9]([O:10][C:11]2[C:19]3[N:18]=[N:17][N:16]([CH2:20][C:21]4[C:29]5[C:24](=[N:25][CH:26]=[CH:27][CH:28]=5)[NH:23][N:22]=4)[C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:30])=[CH:8][C:7]([Cl:31])=[CH:6][C:3]=1[C:4]#[N:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[C:9]([O:10][C:11]2[C:19]3[N:18]=[N:17][N:16]([CH2:20][C:21]4[C:29]5[C:24](=[N:25][CH:26]=[CH:27][CH:28]=5)[NH:23][N:22]=4)[C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:30])=[CH:8][C:7]([Cl:31])=[CH:6][C:3]=1[CH2:4][NH2:5]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 178509925HCID 178509925, Verbindung

Produkt 1

HCID 178509926HCID 178509926, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2,5-dichloro-3-{[5-chloro-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1H-1,2,3-benzotriazol-4-yl]oxy}benzonitrile (283 mg, 0.601 mmol) was dissolved in dry THF (30 mL), cooled to 0° C., and LAH solution (1.20 mL, 1.20 mmol) in THF (1.2 mL) was added. The reaction mixture was allowed to warm to room temperature, and after 2 hours the mixture was cooled to 0° C. and quenched with EtOAc (50 mL). To this mixture was added saturated aqueous Na2SO4 (3 mL), followed 5 minutes later by the addition of water (5 mL). This mixture was stirred for 5 minutes after which excess solid Na2SO4 was added. The mixture was then filtered and solvent removed under reduced pressure. The resulting residue was purified by reverse phase chromatography eluting with 5-95% MeCN/H2O+0.1% TFA to yield the title compound. 1H NMR (DMSO-d6) δ 8.53 (d, J=4.5 Hz, 1H), 8.12 (d, J=8.0 Hz, 1H), 7.98 (s, 2H), 7.89 (d, J=9.0 Hz, 1H), 7.79 (d, J=9.0 Hz, 1H), 7.48 (s, 1H), 7.20 (dd, J=8.0 Hz, J=4.5 Hz, 1H), 6.91 (s, 1H), 6.38 (s, 2H), 4.21 (s, 2H). HRMS (M+1)=476.0363.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. temperatureafter 2 hours the mixture was cooled to 0° C.
  3. customquenched with EtOAc (50 mL)
  4. additionTo this mixture was added saturated aqueous Na2SO4 (3 mL)
  5. additionfollowed 5 minutes later by the addition of water (5 mL)
  6. additionwas added
  7. filtrationThe mixture was then filtered
  8. customsolvent removed under reduced pressure
  9. customThe resulting residue was purified by reverse phase chromatography
  10. washeluting with 5-95% MeCN/H2O+0.1% TFA

Quellen und Nachweise

ORD-Eintrag
ord-1d3b12ecd7334b7b9d699890c98b3299
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

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