Triethylamine → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(chloromethyl)isoxazole-3-carboxamide

HRID 58526

반응식

HRID 58526 반응식
S(Cl)(Cl)=O.O[CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12]([OH:14])=O)[CH:8]=1.[ClH:15].[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH2:26][CH2:27][NH2:28].C(N(CC)CC)C>ClCCl>[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH2:26][CH2:27][NH:28][C:12]([C:9]1[CH:8]=[C:7]([CH2:6][Cl:15])[O:11][N:10]=1)=[O:14]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 80272495-(Hydroxymethyl)-1,2-oxazole-3-carboxylic acid

생성물 1

HCID 66831699N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(chloromethyl)isoxazole-3-carboxamide수율 22%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

Thionyl chloride (0.5 mL; 7.26 mmol) was added to a mixture of 5-(hydroxymethyl)isoxazole-3-carboxylic acid (0.207 g; 7.26 mmol) and stirred at 80° C. for 72 h. The solution was concentrated under reduced pressure and the crude material was dissolved in dichloromethane (5 mL) and added to a mixture of 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.370 g; 1.60 mmol) and triethylamine (0.524 mL; 3.62 mmol) in dichloromethane (5 mL). The resulting solution was stirred at room temperature for 20 min, concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in dichloromethane) to afford N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(chloromethyl)isoxazole-3-carboxamide 0.088 g (22%).

후처리

  1. concentrationThe solution was concentrated under reduced pressure
  2. dissolutionthe crude material was dissolved in dichloromethane (5 mL)
  3. stirringThe resulting solution was stirred at room temperature for 20 min
  4. concentrationconcentrated under reduced pressure
  5. customthe crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록
ord-e8aeaa6de6af4bfbb528e1622eee4e5b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434722B2

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