4-Methylmorpholine → 2-(1-hydroxyethyl)-N-{1-[3-(4-methylbenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenylpentanamide

Temperatur

-20 °C

1.09 g (4.91 mmol) of 2-(1-hydroxyethyl)-5-phenylpentanoic acid are treated with 660 mg (4.61 mmol) of 1-hydroxy-1H-benzotriazole and 990 mg (9.82 mmol) of 4-methylmorpholine and the mixture is cooled to −20° C. After addition of 940 mg (4.61 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride, the mixture is stirred for 30 min. At the same time, the cooling bath is removed. Then, after again cooling to −20° C., 1.00 g (4.09 mmol) of 6-(1-aminoethyl)-3-(4-methoxybenzyl)-1,2,4-triazin-5(4H)-one is added and the mixture is stirred overnight while warming to room temperature. For work-up, the dichloromethane phase is washed with 1N potassium hydrogensulphate solution and then with saturated sodium hydrogencarbonate solution. The dried organic phase is concentrated and chromatographed using the eluent dichloromethane/methanol 100/1 to 30/1.

1. customAt the same time, the cooling bath is removed
2. temperatureThen, after again cooling to −20° C.
3. stirringthe mixture is stirred overnight
4. temperaturewhile warming to room temperature
5. washFor work-up, the dichloromethane phase is washed with 1N potassium hydrogensulphate solution
6. concentrationThe dried organic phase is concentrated
7. customchromatographed

ORD-Eintrag

ord-c4592f1bf72243a2a9a34ab591bdcb15

Quelldatensatz

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06573263B2