Reacción #1881780

Ecuación de reacción

compound

(±)-5-Benzyl-6-(1-bromo-propyl)-3-methyl-5H-isoxazolo[5,4-d]pyrimidin-4-one

3-amino-propionamide hydrochloride

DIEA

→

desired product

Rendimiento 49.0%

(±)-3-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propylamino]-propionamide

Rendimiento 49.0%

Disolventes

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 6 h
2. 2
   Concentraciónconcentrated under vacuum
3. 3
   workup.DISSOLUTIONThe crude product was dissolved in CH3OH
4. 4
   Otropurified by preparative reverse-phase HPLC (CH3OH/H2O) on a YMC S10 ODS 50×500 mm column

Procedimiento

A solution of the compound of Example 1 Step 4 (2.0 g, 5.5 mmol) in EtOH (50 mL) was treated with 3-amino-propionamide hydrochloride (1.72 g, 13.8 mmol) and DIEA (0.53 g, 27.7 mmol). The resulting mixture was stirred at reflux for 6 h, then cooled to room temperature and concentrated under vacuum. The crude product was dissolved in CH3OH and purified by preparative reverse-phase HPLC (CH3OH/H2O) on a YMC S10 ODS 50×500 mm column to afford the desired product as a yellow glass (0.96 g, 49%); 1H NMR (CD3OD): δ 7.37 (m, 5H), 5.65 (d, J=16.5 Hz, 1H), 5.30 (d, J=16.5 Hz, 1H), 4.70 (t, J=6.0 Hz, 1H), 3.15 (m, 1H), 2.94 (m, 1H), 2.59 (s, 3H), 2.49 (m, 2H), 1.93 (m, 2H), 0.89 (t, J=7.5 Hz, 3H); LC/MS (ESI): 370 (M+H)+.

Fuente