反応 #11697

反応方程式

(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

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他after 16 h the resulting yellow solution was evaporated under vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (150 mL)
3. 3
   洗浄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)
4. 4
   乾燥dried over anhydrous sodium sulfate
5. 5
   その他evaporated under vacuum
6. 6
   その他to provide crude product
7. 7
   その他The product was crystallized
8. 8
   workup.DISSOLUTIONby dissolving in warm methanol (40 mL)
9. 9
   workup.ADDITIONadding diethyl ether (100 mL)
10. 10
    ろ過The crystals were filtered
11. 11
    洗浄washed with diethyl ether (30 mL twice), and
12. 12
    その他dried under vacuum

実験手順

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.

出典