3-chloro-5-{[5-chloro-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-1H-1,2,3-benzotriazol-4-yl]oxy}benzonitrile → HCID 178509927, Verbindung

HRID 505528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505528
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([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][C:26]([NH:30]CC6C=CC(OC)=CC=6)=[CH:27][CH:28]=5)[N:23](CC5C=CC(OC)=CC=5)[N:22]=4)[C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:49])[CH:9]=1)[C:5]#[N:6]>C(O)(C(F)(F)F)=O>[NH2:30][C:26]1[N:25]=[C:24]2[NH:23][N:22]=[C:21]([CH2:20][N:16]3[C:15]4[CH:14]=[CH:13][C:12]([Cl:49])=[C:11]([O:10][C:8]5[CH:7]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:9]=5)[C:5]#[N:6])[C:19]=4[N:18]=[N:17]3)[C:29]2=[CH:28][CH:27]=1

Komponenten

3

Edukt 1

HCID 684256713-chloro-5-{[5-chloro-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-1H-1,2,3-benzotriazol-4-yl]oxy}benzonitrile

Produkt 1

HCID 178509927HCID 178509927, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

3-chloro-5-{[5-chloro-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-1H-1,2,3-benzotriazol-4-yl]oxy}benzonitrile (135 mg, 0.195 mmol) was dissolved in TFA (10 mL) and placed in an oil bath at 75° C. After 2 hours, the reaction was allowed to cool to room temperature and was concentrated under reduced pressure. The resulting residue was diluted with CHCl3/EtOAc (4:1, 50 mL) and methanol was added until a solution was achieved. 50% Aqueous sodium bicarbonate (10 mL) was then added. The organic phase was removed and the aqueous was extracted with CHCl3 (25 mL). The combined organic fractions were, dried (MgSO4), filtered and concentrated. The resulting residue was adsorbed onto silica gel with CHCl3/MeOH and purified by automated column chromatography on silica gel (12 g), eluting with 0-5% MeOH/CH2Cl2 to afford the title compound. 1H NMR (DMSO d-6) δ 7.82 (d, J=9.0 Hz, 1H), 7.81 (m, 1H), 7.75 (d, J=9.0 Hz, 1H), 7.58 (m, 1H), 7.55 (d, J=8.8 Hz, 1H), 7.52 (m, 1H), 6.36 (m, 1H), 6.30 (d, J=8.8 Hz, 1H), 6.16 (s, 1H).

Aufarbeitung

  1. customplaced in an oil bath at 75° C
  2. concentrationwas concentrated under reduced pressure
  3. additionThe resulting residue was diluted with CHCl3/EtOAc (4:1, 50 mL) and methanol
  4. additionwas added until a solution
  5. addition50% Aqueous sodium bicarbonate (10 mL) was then added
  6. customThe organic phase was removed
  7. extractionthe aqueous was extracted with CHCl3 (25 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified by automated column chromatography on silica gel (12 g)
  12. washeluting with 0-5% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-a149907fde704567b915bf94ac41d1a6
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

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