Réaction #46612

Équation de réaction

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

Rendement 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

Rendement 76.9%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Concentrationthen was concentrated in vacuo
2. 2
   workup.ADDITIONThe residue was diluted with water
3. 3
   Extractionextracted with ethyl acetate
4. 4
   LavageThe combined organic extracts were washed with brine
5. 5
   Séchagedried over Na2SO4

Mode opératoire

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)+.

Source