Reacción #170308

Ecuación de reacción

6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid

2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate

N,N-diisopropyl ethyl amine

3-methoxypropylamine

→

title compound

Rendimiento 82.7%

N-(3-Methoxy-propyl)-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinamide

Rendimiento 82.7%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   ConcentraciónConcentration and purification by preparative HPLC on reversed phase
3. 3
   Lavadoeluting with acetonitrile/water [0.1% aq NH3 (25%)]

Procedimiento

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (100 mg, 0.32 mmol) in DMF (2 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (114 mg, 0.35 mmol), N,N-diisopropyl ethyl amine (275 μL, 1.6 mmol) and 3-methoxypropylamine (36 μL, 0.35 mmol). The resulting reaction mixture was stirred overnight at room temperature. Concentration and purification by preparative HPLC on reversed phase eluting with acetonitrile/water [0.1% aq NH3 (25%)] afforded the title compound (101 mg, 82%) which was obtained as a white solid. MS: m/e=382.5 [M+H]+.

Fuente