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3,4-dihydro-2H-pyran → 5-bromo-N-methoxy-N-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamide

HRID 334460
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Reaktionsgleichung

Reaktionsgleichung von HRID 334460
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]([N:13]([O:15][CH3:16])[CH3:14])=[O:12])=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]([N:13]([O:15][CH3:16])[CH3:14])=[O:12])=[N:9][N:8]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][O:17]3)[C:5]2=[N:6][CH:7]=1
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Komponenten

5

Edukt 3

HCID 80803,4-dihydro-2H-pyran2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 178502688HCID 178502688, Verbindung

Produkt 1

HCID 583780195-bromo-N-methoxy-N-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamideAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

To a solution of 5-bromo-N-methoxy-N-methyl-1H-pyrazolo[3,4-b]pyridine-3-carboxamide (XIX) (0.250 g, 0.88 mmol) in dry DCM (10 mL) was added 3,4-dihydro-2H-pyran (0.179 mL, 1.98 mmol) and PPTS (22 mg, 0.08 mmol) and refluxed 5 h under nitrogen. Another equivalent of 3,4-dihydro-2H-pyran (0.179 mL, 1.98 mmol) and PPTS (22 mg, 0.08 mmol) was added and the solution was further heated at refluxed overnight under nitrogen. The solution was cooled, diluted with DCM, washed subsequently with a saturated aqueous NaHCO3 solution and brine. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give 5-bromo-N-methoxy-N-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamide (XX) as a viscous liquid (302 mg, 0.82 mmol, 93% yield). 1H NMR (CDCl3) δ ppm 1.51-1.62 (m, 2H), 1.91-2.13 (m, 2H), 2.33-2.44 (m, 2H), 3.40 (s, 3H), 3.66 (m, 1H), 3.75 (s, 3H), 3.87-3.98 (m, 1H), 6.07 (dd, J=10.07 Hz, J=2.52 Hz, 1H), 8.57 (d, J=3.01 Hz, 1H), 8.73 (d, J=3.01 Hz, 1H); ESIMS found for C14H17BrN4O3 m/z 369.4 (M+H).

Aufarbeitung

  1. temperaturerefluxed 5 h under nitrogen
  2. temperaturethe solution was further heated
  3. temperatureat refluxed overnight under nitrogen
  4. temperatureThe solution was cooled
  5. washwashed subsequently with a saturated aqueous NaHCO3 solution and brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-626387eef17645a8b289e28632a4ed01
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08883822B2

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