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Acetic Acid → 1-(4-Methoxy-phenyl)-3-methyl-6-[4-(2-oxo-2H-pyridin-1-yl)-phenyl]-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one

HRID 639591
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 639591
O[CH2:2][C:3]1[C:11]2[CH2:10][CH2:9][N:8]([C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]4=[O:24])=[CH:14][CH:13]=3)[C:7](=[O:25])[C:6]=2[N:5]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[N:4]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.C(O)(=O)C>C(Cl)Cl>[CH3:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([N:5]2[C:6]3[C:7](=[O:25])[N:8]([C:12]4[CH:17]=[CH:16][C:15]([N:18]5[CH:23]=[CH:22][CH:21]=[CH:20][C:19]5=[O:24])=[CH:14][CH:13]=4)[CH2:9][CH2:10][C:11]=3[C:3]([CH3:2])=[N:4]2)=[CH:31][CH:30]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acid3×HCID 12052Triethylsilane3×HCID 10138256HCID 10138256, Verbindung

Produkt 1

HCID 101372751-(4-Methoxy-phenyl)-3-methyl-6-[4-(2-oxo-2H-pyridin-1-yl)-phenyl]-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To 3-hydroxymethyl-1-(4-methoxy-phenyl)-6-[4-(2-oxo-2H-pyridin-1-yl)-phenyl]-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one (65 mg, 0.15 mmol) in CH2Cl2 (10 mL) was added triethylsilane (0.1 mL) and TFA (0.05 mL). After 2 h more triethylsilane (0.2 mL) and TFA (0.1 mL) were added and the reaction was stirred for 72 h. The reaction was not proceeding so the solvents were stripped and replaced with acetic acid (10 mL), triethylsilane (0.5 mL), and TFA (0.1 mL). The reaction was heated 24 h at 80° C. Mass spectra indicated only the acetyl product formed. The solvents were removed. The acetyl group was removed by stirring with LiOH (0.1 g) in THF/H2O for 3 h. The reaction was quenched with 1N HCl, extracted with EtOAc, and dried (MgSO4) to recover the alcohol. To the alcohol in CHCl3 was added PBr3 and the reaction was stirred 24 h. The reaction was quenched with ice water, extracted with CHCl3, and dried (Na2SO4). To the crude bromide were added activated Zn (80 mg) and acetic acid (10 mL) and heated to 120° C. for 24 h. The product was purified by silica gel chromatography using 0-3% MeOH in CH2Cl2 and recrystallized from CH3CN/H2O to afford 22 mg (35%); Mass Spec (M+H)+ 427.3.

Aufarbeitung

  1. customformed
  2. customThe solvents were removed
  3. customThe acetyl group was removed
  4. stirringby stirring with LiOH (0.1 g) in THF/H2O for 3 h
  5. customThe reaction was quenched with 1N HCl
  6. extractionextracted with EtOAc
  7. dry with materialdried (MgSO4)
  8. customto recover the alcohol
  9. additionTo the alcohol in CHCl3 was added PBr3
  10. stirringthe reaction was stirred 24 h
  11. customThe reaction was quenched with ice water
  12. extractionextracted with CHCl3
  13. dry with materialdried (Na2SO4)
  14. additionTo the crude bromide were added activated Zn (80 mg) and acetic acid (10 mL)
  15. temperatureheated to 120° C. for 24 h
  16. customThe product was purified by silica gel chromatography
  17. customrecrystallized from CH3CN/H2O
  18. customto afford 22 mg (35%)

Quellen und Nachweise

ORD-Eintrag
ord-c0c3ee3376724d6bba86e2d2a26bf63f
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07691846B2

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