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Methanol → 7-[3-Pentanoyloxypropylamino]-5-methyl-1H-pyrazolo[4,3-b]pyridine

HRID 620018
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 620018
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]2[CH:13]=[N:14][NH:15][C:7]=12.[C:16](Cl)(=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20].CO.CCOCC>N1C=CC=CC=1.O1CCOCC1>[C:16]([O:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]2[CH:13]=[N:14][NH:15][C:7]=12)(=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 61186Valeryl chlorideHCID 137471677-[3-hydroxypropylamino]-5-methyl-1H-pyrazolo[4,3-b]pyridine

Produkt 1

HCID 212483807-[3-Pentanoyloxypropylamino]-5-methyl-1H-pyrazolo[4,3-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049
Pyridine
Lösungsmittel
HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

7-[3-Hydroxypropylamino]-5-methyl-1H-pyrazolo[4,3-b]-pyridine,* (0.15 g, 0.73 mmol) was suspended in dry pyridine (2 ml) and 1,4-dioxan (2 ml) and cooled in an ice-bath. A solution of valeryl chloride (0.18 ml, 2.1 equiv.) in dioxan (1.5 ml) was added dropwise with stirring and then left at room temperature overnight. Methanol (10 ml) was added and the resulting solution stirred for 1 h and then solvents removed under reduced pressure. The residue was chromatographed on basic alumina eluting initially with ethyl acetate rising to 30% methanol/ethyl acetate. After removal of solvent a colourless oil was obtained, which on trituration with ether gave the title compound as a white solid, m.p. 92°-95° C.

Aufarbeitung

  1. stirringthe resulting solution stirred for 1 h
  2. customsolvents removed under reduced pressure
  3. customThe residue was chromatographed on basic alumina eluting initially with ethyl acetate rising to 30% methanol/ethyl acetate
  4. customAfter removal of solvent a colourless oil
  5. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-f466e1e089224f1c8578aa145e4a2fac
Quelldatensatz
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04818754

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