4-Methoxybenzylamine → tert-Butyl 1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridine-3-carboxylate

HRID 505498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505498
F[C:2]1[N:7]=[C:6]2[N:8]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[N:9]=[C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:5]2=[CH:4][CH:3]=1.[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1>CN1C(=O)CCC1.O>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:8]2[C:6]3=[N:7][C:2]([NH:34][CH2:33][C:32]4[CH:35]=[CH:36][C:29]([O:28][CH3:27])=[CH:30][CH:31]=4)=[CH:3][CH:4]=[C:5]3[C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:9]2)=[CH:20][CH:21]=1

Komponenten

5

Edukt 2

HCID 754524-MethoxybenzylamineHCID 56833644tert-Butyl 6-fluoro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxylate

Produkt 1

HCID 56834061tert-Butyl 1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of tert-butyl 6-fluoro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (2.55 g, 7.14 mmol) in NMP (30 mL) was added 4-methoxybenzylamine (2.80 mL, 21.41 mmol). The resulting mixture was then heated to 80° C. for 2 hours, after which the mixture was diluted with water (200 mL) and extracted with EtOAc (2×200 mL). The combined extracts were washed with water (100 mL), dried with MgSO4, filtered, absorbed onto silica gel (17 g) and removed the solvent in vacuo. This solid was purified on silica gel (80 g) column (0-100% EtOAc/CH2Cl2 to give the title compound. LRMS (M+1)=474.0

Aufarbeitung

  1. extractionextracted with EtOAc (2×200 mL)
  2. washThe combined extracts were washed with water (100 mL)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customabsorbed onto silica gel (17 g)
  6. customremoved the solvent in vacuo
  7. customThis solid was purified on silica gel (80 g) column (0-100% EtOAc/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-5020448ab9594d92a887b8624969bbe8
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

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