Thionyl Chloride → 3-(Chloromethyl)-N,1-bis(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-6-amine

HRID 505500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505500
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]2[C:12]3=[N:13][C:14]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)=[CH:15][CH:16]=[C:11]3[C:10]([CH2:27]O)=[N:9]2)=[CH:5][CH:4]=1.S(Cl)([Cl:33])=O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Cl:33][CH2:27][C:10]1[C:11]2[C:12](=[N:13][C:14]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[CH:15][CH:16]=2)[N:8]([CH2:7][C:6]2[CH:29]=[CH:30][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:9]=1

Komponenten

5

Edukt 3

HCID 24386Thionyl Chloride2×HCID 516892Sodium BicarbonateHCID 56833645{1-(4-Methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methanol

Produkt 1

HCID 568336463-(Chloromethyl)-N,1-bis(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-6-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a slurry of {1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methanol (1.49 g, 3.68 mmol) in chloroform (15 mL) cooled in an ice bath was added thionyl chloride (538 μL, 7.37 mmol). The resulting mixture was then allowed to warm to room temperature and left at room temperature for 30 minutes. The reaction was determined by LCMS monitoring not to be complete not complete, so the reaction mixture was re-cooled in an ice bath, treated with additional thionyl chloride (100 μL), and then stirred at room temperature for 30 minutes. The reaction mixture was then poured into aqueous NaHCO3, extracted into CHCl3 and the solvent removed in vacuo. This residue was purified on a silica gel (120 g) column (0-60% EtOAc/CHCl3 to give the title compound. LRMS (M+1)=422.9

Aufarbeitung

  1. temperatureso the reaction mixture was re-cooled in an ice bath
  2. extractionextracted into CHCl3
  3. customthe solvent removed in vacuo
  4. customThis residue was purified on a silica gel (120 g) column (0-60% EtOAc/CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-6b6dc44e7904488f8c3fe328902798e9
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

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