Nitrogen → 2-[2-(2,5-Dimethyl-2H-pyrazol-3-ylamino)-5-isopropyl-pyridin-4-ylamino]-N-methyl-benzamide

HRID 1472564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1472564
[CH3:1][N:2]1[C:6]([NH:7][C:8]2[CH:13]=[C:12]([NH:14][C:15]3[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=3[C:17]([NH:19][CH3:20])=[O:18])[C:11]([C:25]([CH3:27])=[CH2:26])=[CH:10][N:9]=2)=[CH:5][C:4]([CH3:28])=[N:3]1.N#N>C(O)C.O=[Pt]=O>[CH3:1][N:2]1[C:6]([NH:7][C:8]2[CH:13]=[C:12]([NH:14][C:15]3[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=3[C:17]([NH:19][CH3:20])=[O:18])[C:11]([CH:25]([CH3:26])[CH3:27])=[CH:10][N:9]=2)=[CH:5][C:4]([CH3:28])=[N:3]1

Komponenten

5

Edukt 2

HCID 947NitrogenHCID 462152722-[2-(2,5-Dimethyl-2H-pyrazol-3-ylamino)-5-isopropenyl-pyridin-4-ylamino]-N-methyl-benzamide

Produkt 1

HCID 545889872-[2-(2,5-Dimethyl-2H-pyrazol-3-ylamino)-5-isopropyl-pyridin-4-ylamino]-N-methyl-benzamideAusbeute 61,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-[2-(2,5-dimethyl-2H-pyrazol-3-ylamino)-5-isopropenyl-pyridin-4-ylamino]-N-methyl-benzamide (0.13 g, 0.345 mmole, 1 eq) in ethanol (10 mL) was degassed with N2 and to this PtO2 (0.012 g, 0.052 mmole, 0.15 eq) was added. The resulting mixture was stirred at room temperature under H2 atmosphere with balloon pressure for 10 h. After completion of the reaction, it was filtered through a celite bed which was then washed with ethanol (10 mL). The filtrate was evaporated under reduced pressure to give a solid residue which was purified by washing with diethyl ether to give the title compound as a gray solid (80 mg, 61%). 1H-NMR (400 MHz, DMSO-d6): δ 1.24-1.26 (d, 6H, J=6.76 Hz), 2.05 (s, 3H), 2.75-2.76 (d, 3H, J=4.48 Hz), 2.89-3.10 (m, 1H), 3.53 (s, 3H), 5.96 (s, 1H), 6.67 (s, 1H), 6.85-7.10 (m, 1H), 7.40-7.50 (m, 2H), 7.65-7.67 (d, 1H, J=7.76 Hz), 7.86 (s, 1H), 8.36 (s, 1H), 8.60-8.70 (brs, 1H), 9.89 (s, 1H). LC-MS [M+H]+=379.2.

Aufarbeitung

  1. additionwas added
  2. customAfter completion of the reaction, it
  3. filtrationwas filtered through a celite bed which
  4. washwas then washed with ethanol (10 mL)
  5. customThe filtrate was evaporated under reduced pressure
  6. customto give a solid residue which
  7. customwas purified
  8. washby washing with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9a6da8b46d7249fdb07981c3c2f63e12
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012479B2

Notizen zur Reaktion

Wird geladen…