p-Toluenesulfonic acid → HCID 178437839, Verbindung

HRID 619142

Reaktionsgleichung

Reaktionsgleichung von HRID 619142
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([NH2:14])=[O:13])[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22](C=O)=[CH:23][CH:24]=1.[C:27]1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:27]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[O:18][CH3:17])=[N:14][C:12](=[O:13])[C:9]3=[C:8]([CH2:15][CH3:16])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 312444-MethoxybenzaldehydeHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Produkt 1

HCID 178437839HCID 178437839, VerbindungAusbeute 127,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.0 g, 9 mmol), anisaldehyde (2.45 g, 18 mmol), xylenes (50 ml) and p-toluenesulfonic acid (0.5 g) was refluxed for 32 hours. The reaction mixture was stripped to dryness, treated with ethanol (100 ml) and then again concentrated to dryness. The residue was treated with CHCl3 (100 ml) and 10% K2CO3 (100 ml), the layers were separated and the aqueous layer was extracted with chloroform (3×100 ml). The combined organic layers were concentrated to approximately 25 ml and then combined with silica gel (30 g). The preloaded silica was placed on a silica gel column and eluted with ether/hexanes (8/10) to ether (100%) to afford 1.25 g (41%) of 1-cyclopentyl-3-ethyl-6-(2-methoxyphenyl)-pyrazolo[3,4-d]pyrimidin-4-one, m.p. 135-136° C., after recrystallization from cyclohexane.

Aufarbeitung

  1. temperaturewas refluxed for 32 hours
  2. concentrationagain concentrated to dryness
  3. additionThe residue was treated with CHCl3 (100 ml) and 10% K2CO3 (100 ml)
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with chloroform (3×100 ml)
  6. concentrationThe combined organic layers were concentrated to approximately 25 ml
  7. washeluted with ether/hexanes (8/10) to ether (100%)

Quellen und Nachweise

ORD-Eintrag
ord-f214382a58004ada8dbfce96ae040665
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958929

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