HCID 23402490, Verbindung → 4-amino-3-cyclopentyl-1H-pyrazole-5-carboxamide

HRID 1063813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1063813
[CH:1]1([C:6]2[NH:10][N:9]=[C:8]([C:11]([NH2:13])=[O:12])[C:7]=2[N+:14]([O-])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].C(O)C>[NH2:14][C:7]1[C:8]([C:11]([NH2:13])=[O:12])=[N:9][NH:10][C:6]=1[CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 1

HCID 23402490HCID 23402490, Verbindung

Produkt 1

HCID 234024844-amino-3-cyclopentyl-1H-pyrazole-5-carboxamideAusbeute 103 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

5-cyclopentyl-4-nitro-1H-pyrazol-3-carboxylic acid amide (4.48 g, 20 mmol) and 10% palladium on carbon (800 mg) in ethanol (50 ml) were stirred under hydrogen (50 psi) at room temperature for 18 hours. The reaction mixture was filtered through arbocel and the solid was washed with ethanol (50 ml), methanol (50 ml), dichloromethane (50 ml), and ethyl acetate (50 ml). The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (9:1, by volume) to give 4-amino-5-cyclopentyl-1H-pyrazol-3-carboxylic acid amide (4.0 g) as an off-white solid which was a mixture of rotamers. 1H NMR (400 MHz, DMSO-D6): δ=12.20-12.31 (0.75H, brs), 11.78-11.87 (0.25H, brs), 7.02-7.18 (1.5H, brs), 6.80-6.93 (0.5H, brs), 4.22-4.56 (2H, 2×brs), 2.92-3.02 (1.96 (2H, m), 1.48-1.78 (6H, 2×m) ppm. LRMS (electrospray): m/z [M−H]+ 193. Anal. Found C, 56.12; H, 7.39; N, 27.55. C9H14N4O. 0.2 mol acetone requires C, 56.01; H, 7.44; N, 27.22%.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through arbocel
  2. washthe solid was washed with ethanol (50 ml), methanol (50 ml), dichloromethane (50 ml), and ethyl acetate (50 ml)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (9:1, by volume)

Quellen und Nachweise

ORD-Eintrag
ord-627fe34d89f34a0e95d28b5f2704e505
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06967204B2

Notizen zur Reaktion

Wird geladen…