Reacción #1913232

Ecuación de reacción

diisopropylethylamine

EDC

(E)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylic acid hydrochloride salt

1-methyl-3-(methylaminomethyl)-1H-indole

HOBt

H2O

→

title compound

Rendimiento 48.0%

(E)-N-methyl-N-(1-methyl-1H-indol-3-ylmethyl)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylamide

Rendimiento 48.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat RT
2. 2
   Concentraciónthen was concentrated in vacuo
3. 3
   workup.ADDITIONThe residue was diluted with water
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   LavadoThe combined organic extracts were washed with brine
6. 6
   Secadodried over Na2SO4

Procedimiento

EDC (0.06 g, 0.30 mmole) was added to a solution of (E)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylic acid hydrochloride salt (0.07 g, 0.27 mmole), 1-methyl-3-(methylaminomethyl)-1H-indole (0.05 g, 0.27 mmole), HOBt.H2O (0.04 g., 0.30 mmole) and diisopropylethylamine (0.14 mL, 0.81 mmole) in DMF (15 mL) at RT. The reaction was stirred overnight then was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4. Flash chromatography on silica gel (20% EtOH/EtOAc) gave title compound (0.05 g, 48%) as an off-white solid after drying in vacuo: MS (ES) m/e 389 (M+H)+.

Fuente