Reacción #46612

Ecuación de reacción

EDC

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

2-methyl-3-(methylaminomethyl)indole

HOBt H2O

diisopropylethylamine

→

ODSA

title compound

Rendimiento 76.9%

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

Rendimiento 76.9%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

EDC (0.18 g, 0.96 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 (0.24 g, 0.87 mmole), 2-methyl-3-(methylaminomethyl)indole (0.15 g, 0.87 mmole), HOBt H2O (0.13 g., 0.96 mmole) and diisopropylethylamine (0.45 mL, 2.61 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. Preparative HPLC on a Waters C-18 ODSA column (gradient: 20-100% H2O/CH3CN) gave the title compound (0.13 g, 38%) as a light yellow solid after drying in vacuo: MS (ES) m/e 389 (M+H)+.

Fuente