Reaktion #11697

Reaktionsgleichung

(S)-4-amino-2,3,4,5-tetrahydro-2-benzazepin-3(1H)-one hydrochloride

5-chloroindole-2-carboxylic acid

1-hydroxy-7-azabenzotriazole

1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride

Diisopropylethylamine

→

title compound

(S)-4-(5-chloroindole-2-carbonylamino)-2,3,4,5-tetrahydro-2-benzazepin-3(1H)-one

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeafter 16 h the resulting yellow solution was evaporated under vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (150 mL)
3. 3
   Waschenthis was washed sequentially with 1.0 M aqueous hydrochloric acid (50 mL twice), 1.0 M aqueous sodium hydroxide (50 mL), water (50 mL), and brine (25 mL)
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Sonstigeevaporated under vacuum
6. 6
   Sonstigeto provide crude product
7. 7
   SonstigeThe product was crystallized
8. 8
   workup.DISSOLUTIONby dissolving in warm methanol (40 mL)
9. 9
   workup.ADDITIONadding diethyl ether (100 mL)
10. 10
    FiltrationThe crystals were filtered
11. 11
    Waschenwashed with diethyl ether (30 mL twice), and
12. 12
    Sonstigedried under vacuum

Vorschrift

A mixture of (S)-4-amino-2,3,4,5-tetrahydro-2-benzazepin-3(1H)-one hydrochloride (all of that prepared above), tetrahydrofuran (25 mL), 5-chloroindole-2-carboxylic acid (198 mg), 1-hydroxy-7-azabenzotriazole (150 mg), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (210 mg) was stirred at room temperature. Diisopropylethylamine (202 mg) was added, and after 16 h the resulting yellow solution was evaporated under vacuum. The residue was dissolved in ethyl acetate (150 mL), and this was washed sequentially with 1.0 M aqueous hydrochloric acid (50 mL twice), 1.0 M aqueous sodium hydroxide (50 mL), water (50 mL), and brine (25 mL), dried over anhydrous sodium sulfate, and evaporated under vacuum to provide crude product. The product was crystallized by dissolving in warm methanol (40 mL) and adding diethyl ether (100 mL). The crystals were filtered, washed with diethyl ether (30 mL twice), and dried under vacuum to provide the title compound (181 mg). HPLC/MS [M+H]+, 354.

Quelle