반응 #11697

반응 방정식

(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

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타after 16 h the resulting yellow solution was evaporated under vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (150 mL)
3. 3
   세척this 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
   건조dried over anhydrous sodium sulfate
5. 5
   기타evaporated under vacuum
6. 6
   기타to provide crude product
7. 7
   기타The product was crystallized
8. 8
   workup.DISSOLUTIONby dissolving in warm methanol (40 mL)
9. 9
   workup.ADDITIONadding diethyl ether (100 mL)
10. 10
    여과The crystals were filtered
11. 11
    세척washed with diethyl ether (30 mL twice), and
12. 12
    기타dried under vacuum

실험 절차

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.

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