Reaktion #2161285

Reaktionsgleichung

ethyl 5-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]methyl}-1,2,4-oxadiazole-3-carboxylate

dimethylamine

maleic acid

→

title compound

Ausbeute 89.0%

5-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]methyl}-N,N-dimethyl-1,2,4-oxadiazole-3-carboxamide

Ausbeute 89.0%

Lösungsmittel

EtOH

EtOAc

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed
2. 2
   Sonstigethe residue was purified by flash chromatography (2:98 MeOH/CH2Cl2)
3. 3
   Sonstigeto give a clear oil
4. 4
   workup.STIRRINGThe resulting salt suspension was stirred for 30 min
5. 5
   Filtrationfiltered
6. 6
   Sonstigedried overnight

Vorschrift

To a suspension of ethyl 5-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]methyl}-1,2,4-oxadiazole-3-carboxylate (73 mg, 0.18 mmol) in EtOH (3 ml) was added dimethylamine (2 M in MeOH, 4 mL) and the mixture was stirred overnight at room temperature. The solvent was removed and the residue was purified by flash chromatography (2:98 MeOH/CH2Cl2) to give a clear oil. This was taken up in EtOAc (5 ml) and a solution of maleic acid (15 mg, 0.13 mmol) in EtOAc (2 mL) was added to the solution. The resulting salt suspension was stirred for 30 min , filtered and dried overnight to give the title compound (57 mg, 89 %) as an off white solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 8.62 (d, 2 H), 7.82 (d, 2 H), 7.26-7.35 (m, 2 H), 7.12 (t, 2 H,) 6.82 (s, 1 H), 6.00 (s, 2 H), 4.18 (s, 2 H), 3.03 (s, 3 H), 2.95 (s, 3 H); m/z (APCI+) for C21H19N6O2F 407.1 (M+H)+.

Quelle