Reaktion #1715516

Reaktionsgleichung

1-ethyl-3-(pyridin-4-yl)-1H-pyrazol-5-amine

Boc-L-phenylalanine

EDC

→

101.1.A

Ausbeute 87.0%

Tert-butyl (S)-1-(1-ethyl-3-(pyridin-4-yl)-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate

Ausbeute 87.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas removed by rotary evaporation
2. 2
   Waschenwashed successively with saturated sodium bicarbonate, water and brine
3. 3
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe crude product was purified by silica gel chromatography

Vorschrift

To a 25 ml flask was added 1-ethyl-3-(pyridin-4-yl)-1H-pyrazol-5-amine 20.2.0 (283 mg, 1.50 mmole), Boc-L-phenylalanine (439 mg, 1.65 mmole), EDC (375 mg, 1.95 mmole), 4-dimethylaminopyridine (202 mg, 1.65 mmole) and 5 ml of dichloromethane. The reaction was stirred at room temperature for 4 hours at which time the solvent was removed by rotary evaporation. The residue was suspended in ethyl acetate, and washed successively with saturated sodium bicarbonate, water and brine. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude product was purified by silica gel chromatography to give 101.1.A (568 mg, 87% yield) as colorless amorphous. 1H NMR (400 MHz, CDCl3) δ ppm 8.80 (brs, 1H), 8.56 (d, J=5.8 Hz, 2H), 7.64 (d, J=6.2 Hz, 2H), 7.65-7.63 (m, 5H), 6.68 (s, 1H), 5.32 (brs, 1H), 4.52 (dd, J=14.6, 7.3 Hz, 1H), 3.95 (q, J=7.2 Hz, 2H), 3.25-3.14 (m, 2H), 1.52 (s, 9H), 1.37 (t, J=7.4 Hz, 3H)

Quelle