2-Propanol, 2-methyl-, lithium salt (1:1) → 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

HRID 505527

Reaktionsgleichung

Reaktionsgleichung von HRID 505527
[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][NH:16][C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6].CC(C)([O-])C.[Li+].Cl[CH2:28][C:29]1[C:37]2[C:32](=[N:33][C:34]([NH:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)=[CH:35][CH:36]=2)[N:31]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)[N:30]=1>CN(C=O)C>[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]([CH2:28][C:29]4[C:37]5[C:32](=[N:33][C:34]([NH:38][CH2:39][C:40]6[CH:41]=[CH:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=6)=[CH:35][CH:36]=5)[N:31]([CH2:48][C:49]5[CH:50]=[CH:51][C:52]([O:55][CH3:56])=[CH:53][CH:54]=5)[N:30]=4)[C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6]

Komponenten

5

Edukt 3

HCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 568336463-(Chloromethyl)-N,1-bis(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-6-amineHCID 178509930HCID 178509930, Verbindung

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-chloro-5-[(5-chloro-1H-1,2,3-benzotriazol-4-yl)oxy]benzonitrile (140 mg, 0.459 mmol) and lithium tert-butoxide (37 mg, 0.459 mmol) were dissolved in DMF (1 mL) under N2 and allowed to stir for 20 minutes. After this time, the reaction was cooled to 0° C. and 3-(chloromethyl)-N,1-bis(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-6-amine as a solution in DMF (1 mL) was added dropwise. After 1 hour, the reaction was quenched with saturated aqueous ammonium chloride (3 mL), diluted with water (3 mL) and the mixture was extracted with ethyl acetate (2×25 mL). The combined organic fractions were washed with dilute brine (4×10 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by automated column chromatography on silica gel (12 g), eluting with 0-100% EtOAc/hexanes to give the title compound. LRMS (M+1)=690.5.

Aufarbeitung

  1. waitAfter 1 hour
  2. customthe reaction was quenched with saturated aqueous ammonium chloride (3 mL)
  3. additiondiluted with water (3 mL)
  4. extractionthe mixture was extracted with ethyl acetate (2×25 mL)
  5. washThe combined organic fractions were washed with dilute brine (4×10 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe resulting residue was purified by automated column chromatography on silica gel (12 g)
  10. washeluting with 0-100% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e17ae3e32d1f453b9129fd5df53d89d2
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

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