تفاعل #11697

معادلة التفاعل

(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

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىafter 16 h the resulting yellow solution was evaporated under vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (150 mL)
3. 3
   غسيلthis 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
   تجفيفdried over anhydrous sodium sulfate
5. 5
   أخرىevaporated under vacuum
6. 6
   أخرىto provide crude product
7. 7
   أخرىThe product was crystallized
8. 8
   workup.DISSOLUTIONby dissolving in warm methanol (40 mL)
9. 9
   workup.ADDITIONadding diethyl ether (100 mL)
10. 10
    ترشيحThe crystals were filtered
11. 11
    غسيلwashed with diethyl ether (30 mL twice), and
12. 12
    أخرىdried under vacuum

الإجراء التجريبي

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.

المصدر